Bossk'wassak'Cradossk

Bossk, born to the name Bossk'wassak'Cradossk, was the son of Cradossk, a Trandoshan bounty hunter. Immediately after his hatching, Bossk devoured the nest eggs of his siblings and went on to claim that he was the sole survivor of his clutch. In reality, his sister Doshanalawook survived. From his father, Bossk learned how to boost and steal a landspeeder, as well as inherited both his father's and the Trandoshan species' longstanding hatred for the Wookiees of Kashyyyk. When Bossk reached maturity, he followed in the footsteps of his father to become a bounty hunter. Looking back on his childhood, Bossk regarded fathers as overrated and was uncomfortable with people asking questions about his early life.

Bossk quickly established himself in the bounty hunting trade, becoming known far and wide for his skills at tracking, capturing, and blackmailing enemies of crime lords and tyrants across the galaxy. He also gained notoriety as an exceptionally skilled hunter of Wookiees. He was also a member of the Bounty Hunter's Guild, an institution that regulated the bounty hunting trade. At some point during his career as a bounty hunter, Bossk obtained a modified YV-666 light freighter that was named the Hound's Tooth. This versatile ship became his main transport during his career as a bounty hunter. Bossk was a fervent believer in the Trandoshan goddess known as the Scorekeeper, and believed that he was favored by the deity above other hunters.

In 22 BBY, the Galactic Republic entered the Clone Wars with the Confederacy of Independent Systems. During the opening conflict between the two, the First Battle of Geonosis, renowned bounty hunter Jango Fett was killed by Jedi Master Mace Windu, leaving Jango's young son Boba orphaned. Early in the war, Boba was taken in by Jango's former associate Aurra Sing, who, along with Bossk, mentored and trained the young Fett as part of a bounty hunting crew. Bossk and a Klatoonian bounty hunter hired by Sing named Castas also schemed with Aurra to help Boba exact revenge on Windu. Some time later, the group initiated their plan and had Boba infiltrate the Venator-class Star Destroyer Endurance, which at the time was host to Windu. Boba, whose father was the genetic donor to what would eventually become the Republic's clone army, was able to easily disguise himself as a clone cadet.

While Boba was on the Endurance, Bossk and Aurra followed the cruiser in Jango's ship, the Slave I. Aurra kept in contact with Boba, instructing him on what to do. Their first plan to kill Windu, by placing an explosive in his quarters, failed and Aurra decided to have Boba take down the entire ship. She told him to destroy the Endurances reactor core, which caused a chain reaction that damaged much of the ship's hull. Boba and the cadets he was with were sent to escape pods. The young Fett sabotaged his pod, sending it careening away from where the clones had planned to rendezvous. Bossk and Sing located the pod and had it docked to Slave I. The two hunters opened the hatch to the pod, and they were greeted by Boba. While Aurra and Boba debated what to do with the three cadets in the pod, Bossk went back to the front of the ship and prepared to take off. After detaching the pod, Bossk piloted the ship to the planet Vanqor, where the Endurance had crashed.

Once on Vanqor, the bounty hunters searched the wreckage of the Endurance for survivors. They executed several clone troopers who had survived and took three hostages: Admiral Shoan Kilian, Commander Ponds and another naval officer. Once they had cleared the wreck, they set up a trap for Windu, knowing he would also search the wreck for survivors. Inside the command bridge, Jango Fett's helmet was wired with an explosive that would be set off once it was moved or touched. After completing their task, Bossk and the others returned to Slave I with their hostages. Bossk, Boba, Aurra, and Castas watched from afar as Mace Windu and his fellow Jedi Anakin Skywalker entered the wreckage, and later watched as the bridge exploded. Boba wanted to make sure that Windu was dead, but Aurra told him that there would be nothing to find if they searched for a body.

Castas complained to Bossk about the idea of having to stay on Vanqor any longer, given not only the large population of gundarks but also the fact they were carrying hostages. Aurra reminded him that they could sell them to the Separatists, and, at the insistence of Boba, was convinced that giving the Separatists proof of Windu and Skywalker's deaths could also fetch a price. Aurra, Boba, and Castas boarded speeder bikes to head to the crash site, while Bossk was ordered to watch the hostages. While trying to navigate the wreckage of the Endurance, Sing, Castas, and Boba were nearly killed by falling debris and explosions. Despite Boba's willingness to continue to the bridge, Sing and Castas decided that it would be better to blow up the rest of the wreck and turn back. Bossk, meanwhile, had tied the three hostages together and was dragging them on board Slave I. Aurra contacted him as he was doing so and told him to fire up the ship and that they were going to destroy the rest of the Endurance. Bossk replied that he would have the ship ready for when they arrived.

While Sing and the others rode back to Slave I, they noticed an explosion nearby. Aurra commed Bossk and demanded to know what it was. Bossk looked at the ship's scanners and saw that they had picked up something near where the Jedi had landed their starfighters. Sing told Bossk to jam any communications heading off the planet before the hunters continued on their way back to Slave I. Once they loaded their speeder bikes, Bossk took off and flew the ship towards the wreckage. While flying low, they noticed a Jedi starfighter not far to their right. Castas and Boba recognized the ship as Windu's, and Aurra told Bossk to follow and destroy it. Boba fired at the ship as it flew along the length of the star destroyer, and continued firing on it as Bossk followed it into the atmosphere.

As the starfighter neared two hyperspace rings, Bossk told Boba that he was not in close enough range and would have one shot at destroying them. Boba destroyed one ring, but the starfighter entered the second one and entered lightspeed. With the ship gone, Bossk asked Aurra what their next step was. She opened the hatch to the hostages and decided that they would be the perfect bait for Windu. Aurra turned back to Bossk and said that what they needed to do next was regroup. Unbeknownst to the hunters, Windu had never left Vanqor; both Windu and Skywalker had survived the explosion of the bridge, but were trapped under debris. Skywalker's astromech droid R2-D2 had taken Windu's starfighter and was looking to contact the Republic and ask for aid which arrived soon after and saved the two Jedi.

While Bossk piloted Slave I through space, Aurra and Boba recorded a message for the Jedi. Showing the hostages to the Jedi, Aurra demanded Boba kill Ponds, which he could not bring himself to do. Aurra angrily did so herself, and she taunted Windu to find them before the other hostages were killed. Returning to the cockpit, Aurra told Bossk and Castas that it would only be a matter of time until the Jedi tracked them down. Castas told Aurra that she was in over her head, citing the haphazard planning and increasing stakes. Annoyed by Castas' cowardice, Aurra turned to Bossk and asked him if he was having any doubts as well. Bossk denied doubting her plan and told her that he wouldn't back out, saying he had a lot riding on killing Windu and that he needed the cash.

Castas, however, told Aurra that he was dropping out of the mission. Sing told Bossk to set a course for Florrum, where they would visit an old friend of hers and Castas could find a place to go. On Florrum, the hunters landed at the fortress of the Ohnaka Gang, a pirate group led by Aurra's former partner Hondo Ohnaka. While Sing, Boba, and Castas left the ship to meet with Ohnaka, Bossk stayed behind and watched from the entrance to Slave I, and later re-entered the ship when Ohnaka brought his visitors inside for drinks. While at a bar in the fortress, Aurra noticed Castas attempting to sell information on her location to a contact of his and shot him in the head. Bossk, meanwhile, watched Slave Is scanners for any ships entering the atmosphere. The scanners picked up a Jedi craft, and he alerted Aurra. Sing ordered him to take Slave I to the outskirts of Florrum and prepare the hostages.

The Jedi who arrived at Florrum wasn't Windu, but Jedi Master Plo Koon and Padawan Ahsoka Tano. Sing set up a trap for Windu inside Ohnaka's bar, but when she realized that Windu had not come she contacted Bossk and told him to execute the hostages when she gave the order. Shortly after, however, Tano cut Aurra's comlink antenna, and Bossk was unable to reach her. Bossk decided that, if he didn't hear from her, he would kill the hostages and leave aboard Slave I. Meanwhile in Ohnaka's fortress, Koon and Tano managed to gain the upper hand from Sing and Boba, taking the latter captive. Sing abandoned Boba to the Jedi and escaped on a speeder bike, followed closely by Tano. Boba gave Koon the location of Slave I, and Tano went to rescue the hostages. As Bossk aimed the hostages, Tano arrived and fired at him from her speeder. Bossk jumped to the ground to avoid the blasterfire, dropping his rifle in the process. Tano freed the two hostages, and the freed Kilian picked up Bossk's rifle and aimed it at him. Just then, Sing arrived and crashed her speeder into Tano's, destroying both in an explosion. Sing ran aboard Slave I and prepared to leave, but Tano used her lightsaber to destroy the wing. The ship came spiraling down to the ground, exploding with Sing still inside.

Both Bossk and Boba were taken prisoner by Republic forces that arrived on Florrum soon after, and they were brought to the Republic Judiciary Central Detention Center on Coruscant. Upon arriving at the facility, they were met by Windu. Boba angrily confronted him and told him that he would never forgive him, but Windu told him that he would have to. Over the course of their stint in prison, Bossk saw something in the young Boba and grew protective of him, acting as a bodyguard and protecting him from their fellow inmates. Some time into his own prison sentence, the notorious and famed bounty hunter Cad Bane approached Boba and Bossk and, in return for inciting a prison riot, promised to give them a cut of a heavy price he was to get from criminal mastermind Moralo Eval once free.

To start a riot, Boba had to pick a fight with one of the newest inmates, Rako Hardeen. Bossk watched as Boba started an argument with Hardeen in the cafeteria, and cheered on his young charge as the two entered a fistfight. Hardeen managed to subdue Boba as two prison guards entered the fray, and Bossk stood up from his table. Bossk walked over to the guards and picked them up by their heads, slamming them together and knocking them out. Bossk growled at Hardeen and told him that if he had a problem with Boba, then he had a problem with him too. The Trandoshan picked up Hardeen by his back and hip and threw him across a cafeteria table. Four guards surrounded Bossk, prodding him with electrostaffs. Bossk growled and began attacking them, which encouraged the other inmates in the cafeteria to attack the guards across the room. Amid the riot, Bossk took out several more guards, but ultimately he and Boba were unable to escape, unlike Bane, Eval, and Hardeen.

Some time after the riot, Bane and Eval were rearrested and brought back to prison. At some point after his return, Bane sat with Bossk and Boba during their lunch block to tell them about what had happened after his escape. Bossk and Boba wanted to know when they would get the credits they were promised, but Bane told them that all he had for them was a story. Bane began explaining how he and Hardeen joined Eval in his plot to kidnap Republic Supreme Chancellor Palpatine, though the job went awry when it was revealed that Hardeen was in fact an undercover Jedi Master Obi-Wan Kenobi. Once he finished, he turned to Boba and admitted that his defeat made him wonder if he should retire and let Fett take his place as the best bounty hunter galaxy, though reluctantly added Bossk's name when the Trandoshan hissed at him. As Bossk enjoyed Bane's food after the Duros decided to give it over to him, Boba told Bane that it wasn't his time to retire yet, saying that he and Bossk had a big plan for the future, and invited him to take part in it.

After being released from prison, Bossk and Fett made their way to the Outer Rim world of Tatooine, where they formed a new bounty hunting posse called Krayt's Claw. Utilizing their notoriety and Fett's heritage, Their crew grew to include bounty hunters Dengar, Latts Razzi, C-21 Highsinger, and Oked. The group based themselves in the spaceport of Mos Eisley, where they took a job from the Belugan Major Rigosso to escort cargo on the planet Quarzite. On the day the team planned to depart for Quarzite, Bossk, Razzi, and Oked went to a local cantina to have a few drinks. While Bossk and Razzi sat at a booth, Oked went to the bar, where he began flirting with a Dathomirian woman named Asajj Ventress. When Oked grabbed her arm, she ignited a lightsaber through his stomach, killing him. Once the commotion died down, Bossk ordered her a drink on his tab, then motioned for her to sit down with him and Razzi. Ventress asked Bossk what he wanted, and he introduced himself and Razzi. Razzi went on to tell her that they had a problem. Ventress reached for her lightsabers, and Bossk pointed to the dead Oked and told her that she had killed one of their team.

The Dathomirian sarcastically apologized for the incident. Bossk asked her where she got her lightsabers, and she replied that she had stolen them. Bossk asked if she was a bounty hunter, but she said that she was not, to which the Trandoshan asked if she had ever considered it, given her disposition. Sitting down at the table, Ventress asked if it paid well. Razzi told her that it did, but Bossk got to the point and informed Ventress that they had a job to do and that she could either join their team in Oked's place or be turned over to the authorities. With little choice, Ventress agreed to Bossk's deal and joined him and Razzi. The trio left the cantina and headed for Krayt Claw's base. As they entered their small base, Dengar teased Bossk and asked who his girlfriend was, referring to Ventress. Bossk told him to shut up and continued inside. Bossk greeted Boba as his boss, which prompted Ventress to mock the idea that Boba was their boss. When asked what her name was, Ventress said that she had none. She confronted Boba, mocking his height and age. Bossk hissed at her, then told Fett that they brought her there because she had killed Oked. Putting his arm around her, Bossk coldly told her that if she backed out, they had "another way" of settling her debt.

With the matter cleared when Ventress then agreed to join, Fett told the team that they were ready to go, but Ventress questioned why they hadn't settled the payment first. Boba angrily told her that she would get her cut once the job was finished, same as the other hunters. The group left Tatooine aboard the Hound's Tooth and traveled to Quarzite's space station, where Bossk landed his ship. As they departed their ship, the team was met by Major Rigosso. Rigosso ushered them to a holotable, where he explained the mission. The team would be escorting a subtram in the planet's crystalline caverns. The tram was host to cargo valuable to Quarzite's dictator, Lord Otua Blank. Dengar asked what the cargo was, but Rigosso told him that it was none of the hunter's concern. Rigosso and the bounty hunters headed to a series of turbolifts nearby, where they would descend past the planet's hostile surface and to the crystal underworld below. Bossk entered one of the lifts alone, and altogether he and the others were brought to the tram station.

Once they got off the lifts, the bounty hunters helped Rigosso's soldiers bring the cargo to the tram. As they walked towards the train, Bossk noticed the small box and sardonically asked Razzi if it was all the cargo was. Latts responded that she didn't care what it was, as long as they got paid. Once the cargo was fully loaded, the team split into three groups. Razzi and Highsinger stayed with Rigosso and the cargo, while Fett and Bossk guarded the engine room. Securing the back platform were Dengar and Ventress. Not long into the journey, Dengar contacted the other teams and told them that they had company: a group of Kage Warriors, seeking to hijack the cargo from Rigosso and Otua Blank. Immediately after getting Dengar's transmission, Bossk and Boba noticed footsteps coming from above the tram. A group of three warriors entered the engine room in the front of the car, and three more entered from the back. While Boba fought off the three in front, Bossk shot down one in the back and engaged the others. Bossk and Boba managed to hold them off, and Boba left Bossk to check on the cargo. On the back platform, Dengar was pushed over the side of the tram, and Ventress was alone to fend off the increasing number of attackers. She commed the team and told them that she needed a hand, and Boba ordered Bossk to go help her. While taking out the last of the warriors in the engine room, Bossk threw one against a wall accidentally shorting the lights on the tram. Bossk told Boba that he was on his way and began heading towards the back platform. While in the car between the engine room and the back, he was attacked by a group of warriors. One blew blinding dust into Bossk's eyes, effectively leaving Bossk unable to see. One of the warriors grabbed hold of Bossk's side, while the others pummeled him and brought him closer to the edge of the tram. Although Bossk fought back, he was no match incapacitated and was pushed overboard. He managed to land on all fours and roared in anger as the tram sped away.

Shortly after Bossk was pushed overboard, both Razzi and Highsinger ended up overboard as well. While Ventress and Boba continued with the mission, the other hunters made their way back to the Hound's Tooth. Once the Kage Warriors were defeated, Ventress and Boba entered an argument about the payment. After a brief standoff, Ventress tied and gagged Boba and placed him in the cargo box, which was discovered to be containing a Kage girl, Pluma Sodi, who the warriors were eager to have returned safely. Ventress presented the cargo to Otua Blank and took the payment, and ensured he wouldn't discover Boba inside until she left aboard the tram. Ventress then handed Sodi over to the Kage Warriors for an additional fee. With the promised unmarked credits from Blank and her separate payment from the Kage, Ventress returned to the Hound's Tooth, where she found Bossk and the other hunters waiting for her and Boba's return. Ventress handed Blank's payment, minus her share, to Bossk, who presented the case to the others. Ventress asked Bossk to make sure Boba got his share. Bossk asked where he was, but all Ventress told him was that he would "turn up." Both Razzi and Bossk asked her about her role in the team going forward, but she made no promises and told them that she wasn't part of any team.

Later during the war, Bossk and Fett's syndicate of hunters stopped at a bar at Level 1313 on Coruscant. Bossk was sitting the bar drinking when the Jedi Quinlan Vos entered, posing as a bounty hunter. Vos, who was seeking a lead on the location of Bossk's former teammate Asajj Ventress, tried to get attention by loudly asking if anyone had any job leads, which Bossk coldly rebuked. When Vos casually referenced Ventress, however, Bossk's attention was piqued and he laughed before buying Vos a drink. Bossk inquired if she had stolen a job from Vos, and he instead asked if he knew where she was, to which Bossk answered he had no idea, but after further prodding from Vos, took him to a back alcove where Boba and the other hunters under his employ were seated. Bossk told his boss that Vos was looking for "No Name," and Boba eventually gave the undercover Jedi the information he needed to locate and confront Ventress on Pantora. Before Vos departed, Bossk remarked that he hoped Vos was "man enough" for the task.

Not long after, Boba and Krayt's Claw, which now also included the feared Kyuzo bounty hunter Embo, were sought out by their old associate Ventress, who needed help rescuing Vos from Count Dooku's palace on Serenno. While initially spurning the offer due to Ventress's betrayal of Fett, the hunters, in particular, Bossk and Latts Razzi, were won over when offered 250,000 credits. Bossk and the rest of the hunters provided a distraction while Ventress entered the castle to retrieve Vos and were able to trap Dooku underneath some netting; however, the appearance of the dark side-wielding Vos forced the hunters and Ventress to flee.

Following the end of the Clone Wars and the rise of the Galactic Empire in the stead of the Republic, Krayt's Claw disbanded and Bossk began operating on his own once more. Despite this, Bossk was still a member of the Bounty Hunters' Guild, which had developed a working partnership with the Galactic Empire and pursued acquisitions targeted by a government bounty. He was among a small number of bounty hunters whose Republic criminal records were expunged by the Empire to facilitate their use as independent law enforcers in the Outer Rim Territories. As a licensed bounty hunter, Bossk was also issued with an Imperial Peace-Keeping Certificate. Though licensed under the Empire, Bossk's activities on the criminal fringe were unknown to the government, which suspected him of continuing to operate as such.

Kashyyyk, the homeworld of the Wookiees, was the site of one of the last major battles of the Clone Wars. Following the end of the war, the Empire laid siege to Kashyyyk and conquered the world. The native Wookiees, however, began an uprising following the pacification of their world. Bossk volunteered his services and played an instrumental role in cowing the rebellion. As a result of the Imperial occupation, the Wookiee populations were enslaved. Bossk, an expert tracker and hunter of Wookiees, spent several years locating rebellious Wookiees and delivering them to the Empire. He ran with a posse of Trandoshan hunters during the early years of the Empire, and one of his first Imperial bounties was on a Wookiee named Chewbacca. He also came to recognize the scent of several different clans. During an ill-fated attempt to stop a Wookiee berserker on Ord Mantell, one of Bossk's arms was clean ripped off. He later regrew it, and the arm was filed into an Imperial Security Bureau dossier on the Trandoshan.

One of his most notorious prey was Rutallaroo, an engineer who designed and directed a three-year covert operation aimed at driving Imperial forces away from Kashyyyk. Bossk managed to capture his quarry and deliver him to the Empire for a hefty fee, after which Rutallaroo allegedly "apologized" for his crimes and became a prolific Imperial designer. Though he would often give his Wookiee prey to the Empire, Bossk sometimes fed his prisoners to underworld operations, such as fighting pits and arenas. During his time hunting Wookiees, Bossk faced a mysterious opponent, the Wookiee liberator known only as "Chainbreaker." Chainbreaker led successful attacks against Imperial forces, freeing thousands of enslaved Wookiees and remaining elusive. Chainbreaker became the most wanted Wookiee in the Empire, and Bossk eagerly awaited the day he would be able to take them down. Another rival of Bossk's was Chewbacca, who had escaped Imperial captivity on Mimban with a deserter named Han Solo.

In 10 BBY, Chewbacca and Solo joined a crew led by Tobias Beckett and his lover, Val, who complained about hiring the newcomers in the place of veteran mercenaries such as Bossk or the Xan sisters. The pair became the bane of Bossk's bounty hunting career, and he developed a deep hatred for the two that challenged even his hatred of his father. Bossk tried to capture the two on multiple occasions, including when he found them trawling the sewage seas of Erub II or when he sabotaged their efforts to build a secret Wookiee colony on Gandolo IV. In a breakneck chase to catch the pair along the plasma floes of the Zusi hypertunnel, Bossk shattered the class one generator of the Hound's Tooth. Bossk also engaged them in an explosive blaster battle on the Jurzan spaceport that destroyed both his favorite cantina and a new starship he had recently purchased, the Bitemark. His constant failures to capture the pair not only embarrassed Bossk and damaged his standing with the Bounty Hunter's Guild, but led Cradossk to question Bossk's bounty hunting merits and whether he had been the proper hatchling to survive his clutch.

Despite his frustrations with his uncatchable quarry, Bossk managed to secure several prolific bounties and prided himself on them. Bossk managed to take down the Gibbering Gran of Gibraal and topple the of Qotile, whose title was taken by Bossk after collecting on his bounty. Bossk also collected a bounty on Durgaagoo, the right-hand man of Ploovo Two-For-One.

Around 10 BBY, Bossk was hired by Khamus, heir to the Mourner's Wail Syndicate, to help him infiltrate a sanctuary of the Unbroken Clan and kill Krynthia, the daughter of the syndicate's leader, who was pregnant with his child, though Bossk and the other hunters were unaware that Krynthia was the target or that they were breaking into Unbroken Clan territory. Bossk was part of a group of hunters hired, including Beilert Valance, Nakano Lash, and T'ongor. While the crew made preparations for the job, T'ongor contacted his sister T'onga on the ship's long-range communicator, while Bossk and Valance stood nearby and waited for the briefing. Bossk teased Valance, who was waiting for T'ongor to finish his conversation so he could talk to his close friend, Yuralla Vega. Bossk was impatient with having to wait for Valance to talk to Vega before they could start the briefing, and told the cyborg to be quick with his lover. The annoyed Valance threatened to rip off Bossk's arm after the Trandoshan smacked him in the back of the head, and the two engaged in a brief standoff. Bossk taunted Valance and told him that his new synthetic skin wouldn't make Vega love him, mockingly calling him more of a droid than a man. Bossk quipped that one day he would rip Valance open and see for himself.

T'ongor ended his conversation with T'onga and offered Valance the comm, but as Valance began to contact Vega he suddenly cut the transmission. Bossk called him pathetic, and Valance angrily pinned him against a wall. Bossk incited the Scorekeeper to ward off Valance, telling him that the goddess favored him and that Valance would pay for attacking him. Before their fight could escalate, Lash entered the room and broke up their fight. Lash threatened to kill both of them, but reminded them that the only thing stopping her was the fact she was already down one fighter for the mission. As the group entered the briefing room, Bossk told Lash that if she needed an extra gun, he could contact his old partner, Boba Fett. Lash accepted Bossk's offer and had him arrange a rendezvous with Fett. With the crew all together, Lash began the briefing and explained the mission: the crew would assist Khamus enter a secret base so he could assassinate his target, and in return the bounty hunters would be rewarded one hundred thousand credits.

Their target was located in Coronet City on Corellia, and the hunters began their strike by taking out the guards surrounding the facility. Bossk was tasked with taking down the soldiers in the West Quadrant, which he did with ease. He commed Khamus to tell him about his progress and told his client that the other hunters were having more difficulty taking the tower. Khamus noted that one of the guards escaped Bossk's massacre, and had Lash snipe the guard down from their position. Although Bossk was successful in accomplishing his part of the mission, Fett's lack of discretion entering the base and the sudden murder of Khamus by Lash after discovering that Krynthia was pregnant forced the hunters to make a hasty and violent retreat. Lash, Krynthia, and T'ongor ran out of the facility, where Bossk questioned what was happening. As T'ongor yelled at Bossk to help Lash and Krynthia, he was killed by a stray blast from Fett, who was stopped from sniping the pregnant woman by Valance.

Fett abandoned Valance to the Unbroken Clan's forces, and the cyborg was taken prisoner. The rest of the hunters managed to escape relatively unscathed, though the failed mission would have dire consequences. Because of Lash's actions, the Mourner's Wail Syndicate and the Unbroken Clan entered a war with each other, and she was forced into hiding with Krynthia's daughter after she died during childbirth. Bossk, Fett, and T'ongor's sister, T'onga each grew a vendetta against Lash for what she did. The failed mission also had a longstanding effect on Bossk and Fett; both hunters grew more independent of each other and in their trade, with Fett abandoning the idea of working with a crew altogether.

Five years before the Battle of Yavin, Bossk visited the Outer Rim planet of Lothal to collect a bounty on the Dug criminal Gronson "Shifty" Takkaro, who had jumped bail in the Ahakista system. While the local security Imperial Security Bureau Lieutenant Herdringer was hesitant about allowing the Trandoshan bounty hunter to enter his jurisdiction, he reluctantly acquiesced on the condition that Bossk avoided the use of firepower. Unknown to Bossk, the ISB official he was talking to was actually an impostor, the corrupt ISB Lieutenant Jenkes, who had murdered the real Herdringer and stolen his identity. Jenkes was also in cahoots with "Shifty" Takkaro and informed the Dug fugitive. He also sent Squad Five, a squad of stormtroopers, to kill Bossk.

After landing in Lothal Capital City's spaceport, Bossk encountered a young Force-sensitive Human street urchin named Ezra Bridger. Having been orphaned at the age of seven following the death of his parents, Ezra made his living on the streets of Capital City as a con artist. Posing as an official guide to Lothal, Ezra agreed to lead Bossk to a joint called Ake's Tavern, where "Shifty" Takkaro was reported to be hiding. In return, Bossk promised to pay Ezra a thousand credits and paid the youth an upfront installment of five hundred credits. While traveling on a speeder bus to Ake's Tavern, Bossk paid Ezra the remaining half of his fee.

Upon arriving at Ake's Tavern, Ezra entered the building disguised as a ticket-seller for the Arena Day tournament, which fell on the following day. However, "Shifty" Takkaro had already been warned and Bossk and Ezra soon found themselves under attack from three of Jenkes' associates, the Duros assassin Angrigo and the two Niktos known as the Kratchell twins. These assassins had been sent to protect Takkaro and to kill Bossk and his local guide. During the ensuing shootout, Bossk killed Angrigo and the Kratchells and captured Takkaro. Bossk attempted to interrogate Takkaro but before he could extract any answers, a squad of stormtroopers arrived at Ake's Tavern.

Bossk identified himself as a licensed bounty hunter whose hunt for the bail jumper Takkaro had been sanctioned by Imperial Herdringer of the ISB. When the stormtroopers ignored Bossk, he used a concussion grenade to distract the Imperials before fleeing the tavern with Ezra. Following a skirmish with several stormtroopers and scout troopers, Bossk and Ezra managed to escape on a stolen speeder bike. At Ezra's urging, Bossk reluctantly left his unconscious quarry Takkaro behind; Takkaro was subsequently apprehended by the local Imperial authorities. During their escape from the tavern, Ezra managed to confuse the Imperials by using a stolen stormtrooper helmet to issue false orders. Fleeing into a tunnel, Bossk and Ezra were pursued by a pair of scout troopers on speeder bikes but managed to lose their pursuers by entering the left-fork which led them to the outskirts of the city.

Bossk survived the fight and escape from Ake's Tavern but has sustained a laser bolt shot through his upper shoulder. Following their escape, Ezra demanded a pay hike from Bossk as compensation for being used as a "decoy." The Trandoshan reluctantly agreed to pay Ezra all the money in his ship's strongbox if the youth took him somewhere safe to recuperate from his injury. Bossk was unable to return to his ship Hound's Tooth because the Imperial authorities were after him. Keeping his side of the bargain, Ezra took Bossk to his home: an abandoned communications tower on the outskirts of Capital City. Ezra tended to the wounded Trandoshan and applied a thick bandage around his wounded shoulder. Reflecting on his previous encounter during the day, Bossk realized that he had been set up by Lieutenant Herdringer, who had arranged for the "incident" at Ake's Tavern.

In order to ascertain how the assassins he had encountered earlier had surfaced on Lothal, Bossk decided to visit the local posting agency at Capital City's spaceport to access the Imperial Enforcement DataCore. Borrowing Ezra's jump bike, the two of them traveled to Capital City's spaceport. To avoid detection, Bossk pretended to be a blind invalid with Ezra pretending to serve as his guide. After Ezra used his conman skills to get them past a squad of stormtroopers, the two partners entered the posting agency. While viewing the Imperial records, Bossk and Ezra discovered that Lieutenant Herdringer had died three months ago during a traffic accident and that his colleague Lieutenant Jenkes had stolen his identity. They also learned that Jenkes in the past had managed an illegal gladiator arena on Nyriaan and that Gronson Takkaro had worked as his bookmaster.

Unknown to Bossk and Ezra, Lieutenant Jenkes was monitoring the Imperial Enforcement DataCore. The corrupt ISB agent dispatched a squad of stormtroopers to kill Bossk and placed a bounty on the Trandoshan. After escaping a second attack by stormtroopers, Bossk and Ezra decided to flee to Monad Outpost, where Jenkes was organizing an illegal gladiatorial event called Gladiator Night the following night. Bossk intended to confront Jenkes there and expose his corruption. During their escape from the spaceport, Bossk destroyed an Imperial surveillance remote and knocked out a Ranat bounty hunter and Nimbanel companion, who had wanted to collected the Imperial bounty on Bossk.

After Bossk deduced that Lieutenant Jenkes was the mysterious "Commissioner" who ran the illegal Gladiator Night, Ezra realized that Jenkes would want to kill anyone who knew about his operation including his Xexto mentor Ferpil Wallaway, who had hired Ezra to sell the tickets for the Gladiator Night event. In an attempt to save Wallaway's life, Bossk and Ezra traveled to Wallaway's pawnshop, which lay nine kilometers away from Capital City's spaceport. However, Jenkes had already arrived at Wallaway's pawnshop and killed him with a blaster pistol. Bossk and Ezra arrived just in time to see Jenkes leaving the pawn shop with a large luggage case. Despite failing to save Wallaway's life, Bossk managed to plant a magnetic tracer beacon on Jenkes' speeder. Wallaway's death convinced Ezra to join forces with Bossk to stop Jenkes' plan to steal as much money as he could from the Gladiator Night event at Monad Outpost.

Bossk and Ezra arrived at Monad Outpost, an abandoned mining settlement which lay on the outskirts of Lothal's Capital City; the arena was located underneath the settlement. Lieutenant Jenkes had already arrived and killed the Ishi Tib manning the box office. Before he and his two stormtrooper escorts could leave with the stolen credit chips, Bossk and Ezra intercepted them. After incapacitating his stormtrooper companions, Bossk confronted Jenkes but the lieutenant fled into the arena. Bossk and Ezra gave chase but Jenkes shot the Trandoshan bounty hunter through his right thigh. In an attempt to slow down Bossk, Jenkes seized a comlink from the arena's Pa'lowick master of ceremony and claimed that Bossk was a dangerous fugitive who was wanted by the Empire.

Bossk foiled Jenkes' attempt to frame him by using Ezra's stolen comlink to issue a challenge to the arena's competitors: the Houk Borbig Drob and the Feeorin Warjak. After soundly defeating the two competitors in bare-handed combat, Bossk revealed that Lieutenant Jenkes was actually the shady criminal known as the "Commissioner" and that he had been planning to steal the spectators' credit chips. In addition, Bossk revealed Jenkes' involvement in the murders of Lieutenant Herdringer, the pawnbroker Wallaway, and the Ishi Tib manning the box office. Lieutenant Jenkes then attempted to escape the arena but was thwarted by Ezra who fired a slingshot at him. Shortly later, Jenkes was arrested by the local Imperial authorities.

Following the Gladiator Night showdown, Bossk was exonerated by the Imperial authorities on Lothal who awarded him an undisclosed amount of credits via transfer register. In addition, Bossk was allowed by Commandant Cumberlayne Aresko to take back the corpse of Lieutenant Jenkes as a trophy, who had been executed for his numerous crimes. An official HoloNet News report credited the Trandoshan with saving the lives of numerous civilians and exposing a crime syndicate's operation to defraud gamblers. This brief report omitted any mention of Jenkes, whose actions were deemed an embarrassment for the Empire. Prior to departing Lothal, Bossk paid Ezra everything in his strongbox, which amounted to little more than a paltry sum of ninety credits.

By 7973 C.R.C., Bossk had collected twelve Imperial warrants, eight of them alive.

In the year 0 BBY, Bossk was summoned aboard the Death Star, a moon-sized planet-killing battle station built by the Galactic Empire. During a briefing with two Imperial officers, the Trandoshan learned that an Imperial astromech designated 261 had gone rogue, stolen secret files, and left the battle station. Suspecting treason, the Imperials hired Bossk to retrieve the missing droid.

Bossk then jumped in the Hound's Tooth and took off, hoping to catch the droid before it had a chance to enter hyperspace. Upon exiting the Death Star's atmosphere, the Trandoshan found himself among a fleet of Imperial Star Destroyers. He tuned in the warships' frequency, where they reported the theft of a Lambda-class T-4a shuttle bound for the desert planet Tatooine and piloted by an astromech. Having landed on Tatooine, Bossk spotted the purloined shuttle in the spaceport of Mos Eisley. Although the shuttle had crashed, injuring stormtroopers and civilians in the process, 261 was nowhere near the wreckage. Knowing that the damaged automaton would be looking for new parts, Bossk talked to several street vendors before heading into Chalmun's Cantina for a drink. He notably questioned the surly barman, Wuher, but to no avail. At a dead end, the Trandoshan journeyed to the fortress of Jabba Desilijic Tiure, the Hutt crime lord of Tatooine. There, he learned from EV-9D9 that 261 had indeed been brought to the palace and forced to join its droid pool, but managed to escape.

The Trandoshan ended up discovering that his target had been captured by a clan of Jawa scavengers, whom he started tracking across the barren expanses. Eventually, Bossk confronted the Jawas outside their sandcrawler. Having retrieved the crafty droid, the bounty hunter escorted it back to the Empire.

Shortly following the destruction of the Son-tuul Pride criminal organization by the Empire, Bossk responded to a call on Son-tuul alongside the bounty hunters IG-90, Krrsantan, and Beebox. IG-90 was delayed by Imperial checkpoints while traveling to the planet, and Bossk, Beebox, and Krrsantan waited in a bar for their contact, the rogue archeologist Chelli Aphra. While waiting for IG-90 to show up, Krrsantan joined a fighting pit by killing a contestant and taking their place. When IG-90 arrived, he was denied entry by a bouncer, who the droid quickly killed. Bossk sarcastically asked IG-90 if he was finished, and the droid responded that he had made his point and explained why he had arrived late. IG-90 asked Bossk what he had missed, and the Trandoshan told him that there had been nothing but delays. Beebox informed IG-90 about Krrsantan's distraction. Bossk, IG-90, and Beebox went to the fighting pit, where they observed Krrsantan defeat his opponent. Bossk remarked that, of all the Wookiees he had captured and fed into fighting pits, he had never seen a Wookiee willingly volunteer to enter one. When Krrsantan left the arena, he met up with the other hunters and they found a booth to have drinks. There, they met with Aphra, who detailed an assignment for them. She told the group of hunters about the Imperial Arquitens-class light cruiser transporting Son-Tuul Pride's riches and that she had inside information that would help them infiltrate and steal the large amount of credits.

Aboard Aphra's ship, the Ark Angel, Bossk and the other hunters traveled to Anthan Prime, where they saw the Imperial cruiser carrying Son-Tuul Pride's assets. Aphra told the hunters that once the cruiser entered the asteroid belt, they would make their move. Upset that none of the hunters questioned the fact that Anthan Prime had no asteroid belt, Aphra had her droid 0-0-0 ask the question. She then detonated an asteroid near the cruiser, creating a volley of debris that pummeled the ship. Using the bombardment to her advantage, Aphra fired an ion torpedo at the cruiser, downing its systems for five minutes. With the ship disabled, Bossk Aphra, Beebox, and IG-90 boarded the cruiser's hull from the Ark Angel. To do this, Bossk and Aphra donned spacesuits. Beebox sliced an airlock on the cruiser, and the group entered the ship. Aphra ordered Beebox to seal a door to the crew's quarters while they located the vault holding Son-Tuul Pride's credits. The group found a long hall leading to the vault door, which was guarded by Viper probe droids. Bossk commented that it was unusual for the Empire to utilize droids for such a task, offending IG-90. Bossk saved face by saying that IG units were not the same as the other droids. Aphra told Bossk that the Empire was using droids because they wouldn't let any but the most committed soldiers near the riches, then used an electro-pulse grenade to electrocute the probes. Bossk and IG-90 gunned down the droids while Aphra placed a homing beacon on the vault. She informed the others that they had a short time until the crew of the ship opened the door to their quarters. Bossk hissed and told her to let them, but she refused and explained that they needed secrecy if the mission was to be successful.

Once Aphra put a homing beacon on the vault, Bossk and the others fled the cruiser and returned to the Ark Angel. Aphra had Krrsantan drag a large asteroid into the cruiser via a cable from his gunship. The asteroid punctured the cruiser and sent the credits from the vault jettisoning into space. Krrsantan joined Bossk and the others onboard the Ark Angel, and Aphra ordered her astromech, BT-1, to create an energy field large enough to gather the credits floating in space. BT-1 only managed to accumulate enough to fill two crates, disappointing the hunters. Aphra proposed dividing the credits, but she was met with an angry growl from Krrsantan and Bossk cocking his rifle. Krrsantan and Beebox warned Aphra that she better not have crossed them, but the doctor argued that she couldn't have done so logistically and questioned if they thought she would cross four bounty hunters. Bossk looked her in the eyes and told her that he believed that she would think about it, but added that she wouldn't do it.

The hunters took the credits and left Aphra, who cheerily told them that she would have more work for them in the future. Taking the credits, Bossk and the hunters parted. Unknown to Bossk, IG-90, and Beebox was that Aphra and Krrsantan had double-crossed them. While BT-1 gathered only a fraction of the credits, the rest was collected by satellites set up by Krrsantan. The majority of the credits were then handed to the Empire's Darth Vader, who had sent Aphra to collect the credits to pay for his secret projects. As the war drove on, Bossk continued his bounty hunting work, taking jobs on Taldorrah, Lothal, the Silver Moon of Acomber, Uaua, where he assisted a Quor'sav narcotics agent, Goroth Prime, where he collaborated with a group of Rodians, and a job that involved him silencing the Mad Monks of Xo.

In 3 ABY, Bossk continued his hunt for Chainbreaker, laying a trap for his long-evasive quarry. In order to lure Chainbreaker to the , Bossk altered Imperial flight itineraries so it would appear as though a gunship full of Wookiee prisoners would pass through, which Bossk knew would be an enticing prize for the Wookiee liberator. While he waited for his enemy to arrive, Bossk kept the Hound's Tooth at Asteroid X342 and prepared. As he had anticipated, the Wookiee gunship Liswarr entered the Rycep Belt. In order to board the vessel, Bossk donned a vac suit and gear to travel in open space between the Hound's Tooth and the Liswarr to avoid being detected. Before he made the treacherous approach, however, he was alerted about a high-level communication. Believing it to be a candidate holo-ad for the upcoming Bounty Hunter's Guild elections, he went to press the "egress" button to delete the message but noticed that it was from an Imperial address.

Bossk played the recording, in which Imperial Lieutenant Masil Veit invited him to the Star Destroyer Executor to take part in a hunt for the Millennium Falcon. Before Bossk could learn the rendezvous coordinates, however, the message became distorted and cut off. Not wanting to waste any time reconstructing the message, Bossk hit the egress button and prepared to make the jump to the Liswarr. Once he exited the Hound's Tooth via the airlock, Bossk initiated a quick burn of his jetpack to propel himself towards the Wookiee ship. While navigating the asteroid field, Bossk tried to keep himself calm to avoid setting off any sensors, but as his thoughts dwelled on the Millennium Falcon and Chewbacca, he found himself getting aggravated and hot. A warning from his vac suit reminded him to keep from raising his temperature and he focused on reaching the Liswarr.

Cleanly crossing the gulf from the asteroid field, Bossk reached the Liswarr and dug his claws into the wooden underside of the gunship. Bossk pulled himself across the hull with his claws until he reached the ship's airlock. Not wanting to trip any alarms by touching the air lock's controls, he pried loose some wood that made up the rest of the unusual ship. By doing this, Bossk released the pressurized air in the lock and crawled inside, then put the piece of wood back into place. He then began prying loose wood on the interior entrance of the airlock, eager to begin the hunt. Once inside the ship's main corridor, Bossk inhaled the noxious air to make out what Wookiee tribes were aboard. He could detect the presence of the Chyakk, Koom, and Gkrur clans, but could not tell if a fourth scent belonged to the Kaapauku or Sawa tribes. Although he could not place the name of the fourth scent, he knew it well and recognized it as a relation to Chewbacca. Bossk unslung his Relby and began slowly walking down the corridor.

After about one hundred paces, a hydrospanner went hurling at his head. Bossk batted it away with his rifle and shot a stun bolt in the spine of the thrower, a brown-and-white Wookiee female. While he looked at the unconscious Wookiee, Bossk's instincts kicked in and he turned around to face a short Wookiee charging him with a large piece of tree bark. Bossk caught the branch mid-swing, then kicked the Wookiee in the gut before stunning him. He felt a tingle on his palm and found a pincer flea that had jumped from the Wookiee. Bossk smacked his hand on the wall a few times to kill the pest, then continued his way down the corridor. Bossk reached a door at the end of the corridor. After smashing the door controls with his fist, he entered a wroshyr nursery. Bossk pointed his rifle at the ceiling and began slowly creeping around the trees. In his infrared vision, he could make out the heat outlines of three young Wookiees huddled together. Not wanting to enrage the adult Wookiees elsewhere on the ship any further, Bossk decided to leave them but came up with an alternative plan instead.

Setting his Relby to fire micro-grenades, he fired an explosive at the base of a wroshyr tree. He exited the tree chamber via a different corridor than he entered in, hoping the burning tree would distract some of the gunship's crew while he searched for Chainbreaker. Following the corridor, Bossk could see the door to the bridge at an intersection of hallways. As he approached the center of the corridor to the bridge, however, six armed Wookiees entered from the intersection, two browncoats, two graycoats, one yellow-striped, and one hairless. The six Wookiees charged Bossk, who stunned the female browncoat and knocked out the male browncoat with a heavy uppercut from the butt of his rifle.

Bossk lunged at the two graycoats' legs, easily toppling them and stunning them. Bossk rolled to his feet in time to block a swing of a bronzium pipe from the striped Wookiee. The striped Wookiee threw the pipe away and picked Bossk up by his shoulders. The Trandoshan bent his head forward and bit her nose, and she dropped him as she howled in pain. After stunning her, Bossk came face-to-face with the hairless Wookiee, who he instantly recognized the scent of. Knowing that his opponent was Rutallaroo, whom he had apprehended over a decade before, Bossk shot him with several stun bolts, none of which felled the large creature. Bossk realized that, after years of torture at the hand of Imperials, Rutallaroo would not be taken out by stun blasts. Bossk dropped his rifle and bared his claws to tussle with the Wookiee. Bossk slashed him in his back, but Rutallaroo simply gave the Trandoshan a twisted smile and dug his cracked claws into Bossk's elbow. Bossk kneed the Wookiee in the abdomen and wriggled his arm free, then seized Rutallaroo's neck in a chokehold. Throwing the Wookiee against a wall, Bossk managed to knock him unconscious and smiled at the victory.

Bossk picked up his rifle and looked at his fallen adversaries, noticing that none were armed with blasters or bowcasters; it seemed as though they had only put up enough of a fight to mount a convincing defense without seriously injuring Bossk. While puzzling over this, the doors to the bridge opened for him. Strangely, the scent that emitted from the doorway was similar to the Scorch where he was born. Entering the metallic bridge, Bossk saw his long-sought quarry sitting in a mechno-chair. Bossk growled Chainbreaker's name, and the mysterious figure replied Bossk's full name, Bossk'wassak'Cradossk, in Dosh. Suddenly, Bossk was hit with the realization that his instincts hadn't led him astray and that Chainbreaker was not a Wookiee, but a Trandoshan. After a few moments of silence as Bossk took the fact in, he did something rare and laughed at the absurdity of a Trandoshan who liberated Wookiees. Chainbreaker told Bossk that laughing at her was like laughing at himself, and she bent her head into the light.

Bossk's laughter died when he noticed that Chainbreaker's features were strikingly similar to his. Chainbreaker told Bossk that it was good to finally meet her brother, but he exasperatedly pointed out that he had devoured his fellow hatchlings. Chainbreaker moved her mechno-chair further into the light, revealing three missing limbs and one deformed arm. Bossk deduced that Cradossk must have lied about the story of his hatching. He looked to Chainbreaker and told her to be thankful to him for her life, given that he had not eaten all of her. Chainbreaker scoffed at the notion and pointedly told him that she thanked the Wookiees for her survival. Chainbreaker revealed that she had been given to Wookiees by Cradossk in exchange for rum, and went by the name Doshanalawook. Bossk laughed and told her that Wookiees ate Trandoshan eggs, but Chainbreaker stared at him and asked if he had ever witnessed one do so. Bossk tried to back up what he believed, but his sister informed him that most Trandoshan beliefs about Wookiees were lies meant to incite hatred. Bossk could smell the clan-stench of Chewbacca on Chainbreaker, who explained that she had been mentored by Chewbacca's father, Attichitcuk.

Although he was confused and had many questions on his mind, Bossk decided that enough was enough and ordered Chainbreaker to bring the Liswarr to Asteroid X342. Chainbreaker told Bossk that she had already set the course. Bossk correctly guessed that Chainbreaker had known his plan. Chainbreaker revealed that, although Bossk's plan was better than anyone else's who had tried to capture her, she could tell that there was no Wookiee prison ship because it did not appear on any of the hundreds of Imperial timetables she received besides the one Bossk had altered. Bossk asked if she truly meant hundreds, and she invited him to tour the consoles and holographic maps in the bridge. Keeping his rifle aimed at his sister, Bossk looked around and found a projection table at the center of the bridge that featured information on him. Chainbreaker explained that she kept tabs on anyone who threatened Wookiee liberation, and dismissed Bossk's claims that Wookiee freedom was treason to Trandoshans.

While perusing the information Chainbreaker had on him, Bossk discovered that she had been intercepting his private communications. Bossk was shocked, as the Hound's Tooth had high-grade encryption transceivers that were used on Star Destroyers. Chainbreaker plainly explained that it was the Wookiees who had designed such technology. Bossk snarled and activated playback of his latest message from Lieutenant Viet about hunting the Millennium Falcon. Before he could watch the full message and learn the rendezvous, Chainbreaker used the console on her mechno-chair and disrupted the hologram. Bossk slammed the console in a failed bid to make the message reappear, then ordered Chainbreaker to replay it. Chainbreaker smiled and told him that she would only do so if he did her a favor. Bossk snapped that he didn't do favors, and she changed her wording to suggest a trade. Bossk walked towards her chair and set his rifle to its most painful setting. Staring at Chainbreaker, Bossk told her that, sister or not, he would inflict intense pain and kill every being on the ship unless she replayed the message. Unfazed, she replied that she wanted him to see the truth and let him reconsider his threat. Just as she finished speaking, Bossk heard the footsteps of Wookiees coming close to the bridge. He shot at the door controls, but before it could close a series of spears entered the cabin. Bossk dodged the spears and ducked behind Chainbreaker's chair.

Chainbreaker ordered both the Wookiees and Bossk to hold their fire. Bossk at first refused, but upon seeing the Wookiees he had beaten earlier enter the room fully armed, he relented. Bossk muttered that not all of them could have been immune to his stun blasts, but Chainbreaker confirmed that each Wookiee had endured far worse under the Empire. Bossk wedged his rifle into Chainbreaker's head and told the Wookiees that he would kill her if any of them moved. Chainbreaker informed Bossk that only she could replay the message, and he realized that his chances of escaping the ship were nil. Bossk acquiesced to Chainbreaker and asked what favor she wanted. To his astonishment, she asked that he stop hunting Wookiees for good. Bossk involuntarily let out a burst of nervous laughter and asked if she was serious. She explained that she didn't want him to stop bounty hunting, she just wanted him to stop hunting Wookiees.

She explained that the galaxy was replete with bounties for criminals and murderers and that they would be a better quarry for Bossk than Wookiees. Bossk retorted that Trandoshans were meant to hunt Wookiees. Chainbreaker took a jab at his refusal and said that he was afraid to go after other bounties. Bossk let out a stifled laugh, angry at her comment. Bossk angrily told her that his bounties went far beyond the Wookiees. In an attempt to prove his prowess, Bossk mentioned collecting on the Gibbering Gran of Gibraal, though Chainbreaker pointed out that the Gran was respected by no one. Bossk tried saving face by mentioning Dugaagoo and the monarch of Qotile, but Chainbreaker broke his facade by noting how he could not collect on Dugaagoo's boss and that the title of Monarch of Qotile was meaningless. Defeated, Bossk simply told her that insults wouldn't change his mind. Chainbreaker remained calm and apologized, saying that she simply meant to point out that he was meant to go after greater bounties than common lowlifes or Wookiees.

Eager to get his message and get back to his ship, Bossk reluctantly agreed to her terms. Chainbreaker ordered Bossk to say it aloud to the Wookiees, though he couldn't look to meet their gaze as he spit the words out. Satisfied, Chainbreaker played the end of the message, which revealed that the rendezvous with the Imperial fleet was at eight-four-two-point-three in the Anoat System. Chainbreaker also handed Bossk a datacube which she said contained information about how baseless claims and lies had shaped the divided history between Trandoshans and Wookiees. Keeping his rifle aimed at her, Bossk began to slowly back out the room as Chainbreaker optimistically told him that reconciliation between Trandoshans and Wookiees was possible. Halfway to the exit, Bossk turned to Chainbreaker and asked if she knew who his target was in the Imperial job. She nodded and told him that it would be a good test to see if he would keep his word. Bossk asked if there would be repercussions if he broke his promise.

Chainbreaker informed him that he would be hunted down and would face a wrath unlike anything he would ever know, but also told Bossk that that wouldn't happen because she knew he would keep his word. Bossk questioned why she would trust him, and she replied that she trusted him because he was her brother. As he flew back to the Hound's Tooth with his jetpack, Bossk felt colder than he had on the jump to the Liswarr and kept repeating "Doshanalawook" to keep himself awake. Despite his best efforts, he couldn't muster the ability to hate his sister. Once at the airlock of the Hound's Tooth, Bossk looked back to where the Liswarr was and noticed it had already gone. Confused by the entire experience, Bossk questioned to himself if he had become stricken with , had dreamed up the situation like the lies his father told him, or if the galaxy was changing and he was becoming involved in it. Back on board his ship, Bossk put these questions aside and began to think about Chewbacca.

After leaving the Rycep Belt, Bossk traveled to the rendezvous coordinates and landed the Hound's Tooth aboard the Executor, Bossk waited for orders alongside Dengar, IG-88, and, as he predicted would be there, 4-LOM and Zuckuss. Boba Fett was the last to arrive, and he nodded to Bossk and Dengar as he disembarked. Bossk greeted Fett by just his first name, as he had since he was a child, much to the annoyance of Fett. One of the Imperial officers collected the bounty hunters together and brought them to the bridge. Along the way, Dengar and Fett bet 20 credits that their target would be the Millennium Falcon. Bossk mused that he had dropped another score to take this job, though looked forward to killing Chewbacca. Dengar questioned how Solo and Chewbacca ended up wanted by so many individuals and organizations and survived. Bossk guessed that joining the Alliance to Restore the Republic may have helped them despite their stupidity. Once at the bridge, the hunters were made to wait once more. Vader soon arrived and began sizing up Dengar and IG-88. Admiral Firmus Piett murmured to his fellow officers that the hunters were scum, to which Bossk uttered an unmistakable warning to the Admiral in his native Dosh.

As Fett had predicted, their target was the Falcon. The anticipation among the hunters lasted for only a moment before an Imperial officer announced that the ship had been located. The hunters returned to the hangar bay, where 4-LOM and Zuckuss quickly departed. Bossk and Dengar were ready to leave but were puzzled by Fett's choice to stay back. Bossk questioned what was going on in his head, and Fett explained that as stupid as Solo was he wasn't going risk his ship against the Empire and that something was wrong. Bossk cleared his throat and mockingly asked Fett why, if he knew Solo so well, he hadn't brought him in yet and asked if he was losing his touch. Dengar smirked and suggested that they team up to track Fett together, to which Bossk sarcastically remarked that "Krayt's Claw lives again." Bossk added that it wouldn't happen and teased Fett about his reluctance to work with a team. Fett stated that he wouldn't work with a team again after the Corellian job, which made the three hunters grimace at the memory of the failed mission. Bossk reminisced about the better runs they'd had as Krayt's Claw. As the three hunters stood silent, a young Imperial officer ran to his comrades and told them that an officer named Captain Needa was dead, which proved Fett right that the Empire lost the Falcon.

Fett proposed that they could ride together again to track Solo, which piqued Bossk and Dengar's attention. Fett, however, was going to double-cross them. Once the three had returned to their ships, Fett gave them a series of decoy coordinates, a trick Bossk had once taught him. Bossk and Dengar unknowingly jumped to decoy points, while Fett faked his jump and stayed back with the Imperial fleet. Bossk was eventually unsuccessful in his hunt for Solo and Chewbacca, and Fett later received a carbonite-frozen Solo from Vader.

Bossk was displeased with Fett's success in capturing Solo, venting his anger at the Carbon Score Cantina on Burnin Konn. While there, he was approached by Aphra and Krrsantan, the former of whom mocked the Trandoshan. Bossk angrily stood up and threw his drink to the ground, ignoring the bartender's pleas for him to stop. Bossk charged Krrsantan, and the two engaged in a fistfight. Aphra sat down and started mixing a drink, and told Bossk to leave Krrsantan alone and revealed that she had nicked his blaster during the skirmish. The doctor mentioned the botched Corellia job, though Bossk was unmoved and demanded she explain why she and Krrsantan were there. Aphra explained that Nakano Lash had resurfaced with a bounty on her head, piquing Bossk's interest.

As it turned out, Bossk was not alone in his hunt to try and locate Lash. Lash's return drew the attention of many bounty hunters, but more importantly, Valance, Fett, and T'onga were all on the hunt to find and kill her. With Aphra's intel, Bossk traveled to the graveyard planet Galmerah, where Lash had recently been sighted. Upon landing, Bossk was met by one of the graveyard's caretakers, who asked for alms from the Trandoshan. Bossk yelled at the caretaker, who ran away from him. Also on Galmerah was Valance, who Bossk encountered at the grave of Lash's parents. Bossk pointed his rifle at Valance and accused him of being in on Lash's betrayal during the Corellia job. Valance reminded Bossk that he was the one hunter to escape unscathed, unlike Valance and the others. Bossk waved away that fact and told Valance that it would still be worth it to kill him, given that Valance's droid had discovered the coordinates of Lash.

Bossk fired a dioxis grenade at Valance, who hid and took cover. Bossk mocked his former partner as he searched through the mist for him. Valance fired at Bossk from higher ground, and the Trandoshan fired another grenade at him, which pushed the cyborg to the ground. Valance tried using his palm blasters at Bossk, but they malfunctioned and he ran through the ruins as Bossk continued firing his barrage of explosives at him. Valance threw a rock at Bossk, then punched him hard enough to momentarily knock him back. Bossk threw a punch in retaliation, then jumped over Valance before he could grab his leg. The Trandoshan continued pummeling Valance, though he was pushed to the ground after Valance slammed his head into Bossk's. Before Bossk could stand back up, Valance struck him with a large rock. Valance mused that he could kill Bossk if he wanted, but instead cuffed him so he could remember his loss.

Bossk remained cuffed to a column on Galmerah, where he was found by Fett. Fett interrogated Bossk about where Valance had gone. Bossk told Fett that Lash had given Valance coordinates, then suggested that he release him and they could work together to find Valance and Lash. Fett instead mocked the idea, telling Bossk that there was no chance they would work together. Fett then kicked Bossk hard in the jaw, knocking him unconscious and leaving him on the graveyard world.

Sometime later, Bossk returned to work and was hired by Bib Fortuna, right-hand-man to Jabba the Hutt, to infiltrate the Great Hunt of Malastare to help coerce Exum Jermit, the Second Vice Chair of the InterGalactic Banking Clan, to stop conducting business with one of Jabba's competitors and redirect his business to Jabba's criminal empire. As part of the job, Bossk was to join the prey of the Great Hunt, prisoners and other low-level offenders captured and forced to fight for their survival. Bossk saved a small group of prey from a Gran hunter, easily digging his claws into his head, killing him. The group thanked Bossk, but the Trandoshan coldly told them that they still hadn't survived the night and that only one of them may live. One of the Malastare Hunting Club's probe droids captured the killing, though Bossk ignored the group's requests that he destroy it, instead wanting the footage seen by Jermit. Bossk violently subdued one of the detracting runners and forced the others into submission to his orders. While Bossk and the prey walked through the forest, they selected a clearing to set up a trap. One of the runners stood in the center of the clearing, where any hunter trying to kill them would be impaled by several spears from the caves above.

Two Dug hunters located the clearing in search of Bossk, where one entered the trap and was skewered. Bossk snuck up behind the other, who managed to counter Bossk's attack and hit him in the jaw. One of the prey shot the Dug while Bossk fought him, angering the Trandoshan. The runner told Bossk that they were returning the favor of saving them from the Gran, but instead of thanking them, Bossk told them not to get between him and his targets ever again. The news of Bossk's presence brought Exum Jermit out of his private club and onto the hunting field, eager to kill the Trandoshan himself. While Jermit and his team tracked him, Bossk and his group made their way to the edge of the valley, where they could see Bib Fortuna's ship. The group of runners were unaware that it was Fortuna's ship, and Bossk promised them that it was a way off-world as part of his plan to draw out Jermit. Using the ship as bait, Bossk sent the group running towards it across the open field, where all but one was gunned down by Jermit's hunting group. While they were massacred, Bossk disappeared from their sight and buried himself underneath the sand. When Jermit's hunting group ceased fire, they noticed that Bossk was not present with the prey.

At that moment, Bossk burst from the ground and slashed the eyes of one hunter, setting off his detonator in the process. The explosion killed two more hunters, and Bossk eluded the blast. While Jermit and his companion Grummgar got their bearings, Bossk leaped from the smoke and threw his saber into the head of another hunter, then attacked Grummgar. Bossk and Grummgar entered a fistfight, but the large Dowutin was no match for the agile Bossk, who slammed a rock into his opponent's head. As Bossk walked away from the unconscious Grummgar, the surviving prey called out Bossk for using them. Bossk snidely remarked that he had been right earlier; one of the prey had survived.

Jermit and his remaining hunters ran towards Fortuna's ship in order to escape Bossk, though Fortuna refused him entry unless he reneged on his contract with Jabba's competitor, lest he be killed by Bossk. Jermit refused the offer, and Fortuna had Bossk sneak up behind the Muun and kill him. Bossk followed Fortuna onto his ship, where Jabba's advisor complimented his work and offered him some of the food he had taken from Jermit's hunting club, though Bossk was disinterested in the cooked meats. Bossk asked Fortuna about another job he had been told about, and Fortuna informed him that it would be a difficult challenge, exciting the Trandoshan.

Fortuna informed Bossk that Jabba had placed a bounty on Boba Fett, who had lost Han Solo while trying to bring the frozen smuggler to the Hutt. While en route to deliver Solo to Jabba and collect the Hutt's bounty on him, the carbonite holding Solo captive became unstable and Fett had to make a quick stop on Nar Shaddaa to have it fixed, though things went awry when agents of the revived criminal organization Crimson Dawn stole Solo from him for their own purposes. Believing Fett to have sold Solo, Jabba placed a price on his head with the return of Solo as a bonus. With the information given to him by Fortuna, Bossk tracked Fett down to Jekara, where Crimson Dawn was hosting a large auction attended by nearly every crime organization in the galaxy.

Fett had arrived on Jekara to claim Solo from Crimson Dawn, but after landing his ship he was attacked by Bossk. Bossk fired a grappling line around Fett, snarling that Jabba had some questions for him. Fett used his flamethrower to create a cloud of steam as cover, then cut the wire restraining him. He then fired a rocket from his jetpack, which Bossk dodged. Although Bossk dodged the rocket itself, the projectile hit a ship behind him, destroying it and disintegrating his legs in the blast. Bossk crawled from the wreckage, where Fett stood over him. Bossk was not concerned with his legs, given that they would grow back. The Trandoshan faced Fett, asking what would he would do with him. Fett told him that he would not kill him, instead tying him to a rock as a message to any bounty hunters who were trying to collect the bounty on his head. Bossk pleaded with Fett not to leave him out in the cold, but Fett refused and continued on his way to retrieve Solo.

Bossk was left out in the cold, cursing Fett for defeating him and leaving him stranded. Soon after, he was discovered by a crew led by the bounty hunter T'onga, who had been searching for Valance. T'onga recognized Bossk from Nakano Lash's crew. Zuckuss sensed that the Trandoshan could be useful, but then retracted his statement when he saw the condition that Bossk was in. T'onga wanted to load Bossk into the medical bay of their ship, the Edgehawk, despite protestations from Tasu Leech. After Leech suggested eating Bossk, the Trandoshan awoke from his frost-bitten unconsciousness and lunged at Leech, grabbing him and holding a knife at his throat, saying that he would kill the crew and then proceed to track down Fett and Valance. T'onga, having realized Bossk had seen Valance. Bossk was taken aboard the ship, donning a cloak to warm up and eating protein in an attempt to help his legs grow back. Bossk asked Leech if Gands were high in protein, which worried Zuckuss. After the crew failed to rescue Valance, Bossk eventually joined T'onga's crew.

Sometime after Fett collected the bounty on Solo, Bossk and a group of fellow hunters took a job to hunt rebel Lando Calrissian, who they tracked down to the planet Arkanis. Unexpectedly, Chewbacca and rebel leader Leia Organa were sent to help Calrissian, who managed to outrun Bossk and other hunters trying to capture him. As Organa and Calrissian found each other and prepared to leave, Bossk's accomplices electrified the nearby Chewbacca and brought the Wookiee to Bossk. Bossk was elated to have Chewbacca in his hands and decided to order drinks for the hunters who brought him in. In the nearby cantina, Bossk stood at the bar with the captive Wookiee sitting on the floor next to him. Impersonating the bounty hunter Boushh, Organa entered the cantina and told Bossk that she would see him on Tatooine after Bossk mentioned bringing Chewbacca to Jabba. Bossk and the other hunters were taken aback by Boushh's statement and knew that something was up, so he sent them to go see what Boushh was doing.

Organa and Calrissian managed to take out the two hunters sent by Bossk, who followed them in the Hound's Tooth. Bossk jumped from his ship and fired at Organa, who he believed to be Boushh trying to take Calrissian for himself. Bossk and Organa engaged in a shootout, but she outsmarted the Trandoshan by firing at the rocks above him. The stones hit Bossk's first-gen X-45 rifle, which jammed and allowed Organa to corner him. Bossk suspected that Boushh wasn't himself, though Organa offered to let Bossk go if he traded Chewbacca in exchange for his gang. With no other options, Bossk relented and traded. Bossk chastised his boys after they were returned to him, then they boarded the Hound's Tooth and left Arkanis.

Bossk later met up with Fett at Jabba's Palace, and subsequently accompanied Jabba's retinue aboard the Khetanna.

In 9 ABY, during the time of the New Republic; Charr, one of the Hunters who participated in the Hunters of the Outer Rim event, praised Bossk for being his inspiration to strive to be the best. He also showed disappointment with Bossk's absence during the sporting event, wanting the chance to spar with the bounty hunter.

Around the same time, Bossk and the rest of T'onga's crew undertook a job on the Halcyon for the Black Sun to capture or kill the Balosar Stolak Vandello, who was in debt to the syndicate.

Bossk was a moody and serious, yet ruthless and efficient bounty hunter who believed in upholding the Bounty Hunter Code at any cost. He did not like other bounty hunters or governments interfering with any of his bounties, nor questions about his past with his father. While Bossk tended to work alone, he was also capable of working with other individuals, including Boba Fett, Aurra Sing, and Ezra Bridger.

As a businessman, Bossk was also known to keep his promises to the letter of the law. He was also known as a fair and honest combatant, although later cited preferring "a big rock" to honor in combat. Bossk believed the hunt itself mattered more than credits, yet he found himself in need of money on several occasions. He was impatient and did not believe in subtlety, getting the job done however he thought was appropriate.

The Trandoshan viewed instinct as "fierce, not cruel" and believed that the only purpose of the Wookiee species was to be hunted. At an early age, he learned to despise the species and would inflict gruesome injuries on the Wookiee slaves that the Trandoshans had. Despite swearing to stop hunting Wookiees after being forced to do so by his sister, who knew he was one to keep his word, Bossk pursued the bounty on Chewbacca when his hunt for Lando Calrissian was not proving fruitful.

Bossk earned his reputation as one of the best bounty hunters in the galaxy, and during the Imperial Era, his reputation was akin to that of a folk-hero. Although Bossk had some honor, he was also capable of grotesque cruelty, skinning his prey on multiple occasions.

As a bounty hunter, Bossk was a physically fit and a skilled fighter. He developed a fearsome reputation as an effective hunter of Wookiees, a species that shared the Kashyyyk system. While Bossk often wielded a mortar gun, he was also skilled in unarmed combat. As a Trandoshan, Bossk was considerably strong and had natural regeneration abilities. On one occasion, he took on two gladiatorial fighters and bested them both in a fight. Bossk lost limbs to combat on multiple occasions, ranging from an arm to both of his legs, only to later regenerate them and return to bounty hunting.

Bossk's primary weapon was a Relby-v10 micro grenade launcher, a weapon that matched his direct and destructive style. He also utilized a YV-series light freighter named the Hound's Tooth as well as the Z-95-AF4 Headhunter Nashtah Pup. During the Galactic Civil War, Bossk carried a small saber with him, and also used a first-generation X-45 blaster rifle. Among his arsenal he used dioxis grenades as well as proximity mines.

He wore a simple yellow pressurized suit and a white flak vest in favor of armor, giving him fuller freedom of movement. Additionally, he preferred to not use footwear such as boots, allowing his clawed feet to be weapons in his arsenal.

Bossk first appeared in the 1980 film Star Wars: Episode V The Empire Strikes Back. Prior to the release of the movie, he appeared in a mail-in flyer that revealed his role in the movie. In the The Empire Strikes Back, Bossk was played by the actor Alan Harris, who reprised his role in Star Wars: Episode VI Return of the Jedi. Bossk was voiced by Dee Bradley Baker in the animated series Star Wars: The Clone Wars. Bossk's animation model was redesigned between his appearances in season two and four to more closely resemble his film counterpart, as the more colorful designs for the Trandoshans in season three caused the show's staff to regret how simple his appearance was.

In the fourth draft of The Empire Strikes Back screenplay, Bossk was described as a slimy, tentacled monster with two huge bloodshot eyes in a soft baggy face.

Bossk's outfit was actually recycled from a 1966 Doctor Who serial titled The Tenth Planet. The suit itself was actually a High-Altitude Windak Pressure Suit, a suit used by the British Royal Air Force in the 1960s.

Before the cancellation of The Clone Wars TV series, Bossk was set to make an appearance during a four-episode arc starring Boba Fett and Cad Bane. In a clip revealed during the Animated Origins and Unexpected Fates panel at Celebration Orlando in 2017, Bossk and Embo were seen siding with Bane during a stand-off between Fett and other bounty hunters. Bossk then suggests that Bane give Fett his chance to prove himself.

Writer Jon Kasdan originally desired to include Bossk in the 2018 Star Wars Anthology film Solo: A Star Wars Story. However, Kasdan ultimately concluded that there was no place for Bossk in the film. In Kasdan's drafts for Solo, Bossk was part of the Cloud-Riders and served as Enfys Nest's second-in-command, only to abandon her by the end of the film. Though Kasdan fought to keep this scene, he was overruled.

Although Ultimate Star Wars, New Edition stated that Bossk and Fett escaped from the Republic Detention Center, Star Wars: The Secrets of the Bounty Hunters later established that they were released.

Bossk appeared in the LEGO Star Wars: The Freemaker Adventures Season Two episode "Return to the Wheel," which premiered on August 3, 2017. He and several bounty hunters including Dengar, 4-LOM, IG-88, and Zuckuss captured the Freemakers but they escaped after Kordi created a fight between the droid and organic bounty hunters.

• LEGO Star Wars: Droid Tales — "Flight of the Falcon"
• LEGO Star Wars: The Freemaker Adventures — "Return to the Wheel"
• LEGO Star Wars: The Force Awakens
• LEGO Star Wars: The Skywalker Saga