Chegg was a male Keshiri who served as captain of the Southern Star which was sent by the Lost Tribe of Sith government in Tahv on an exploratory mission to the polar continent of Eshkrene in 2974 BBY. Prior to this mission, he reluctantly took on the Human Sith outcast Parlan Spinner as a crew member aboard the Southern Star. During this voyage, a second human stowaway—the Sith princess Takara Hilts—surfaced on his ship. While exploring Eshkrene, Chegg and his Keshiri crew attempted to kill the two Humans when they tried to desert the ship. During the pursuit, Chegg and several of his crew were murdered by several members of the Doomed, the descendants of ancient Jedi and Dark Jedi stowaways from the Hundred-Year Darkness.
Chegg was an Alanciari Keshiri lived on Alanciar, one of the two main landmasses on the planet Kesh. At some point prior to 2974 BBY, Chegg became the captain of the sailing ship Southern Star. As a captain, he was known as a tough disciplinarian and believed that everyone who ever got on his ship had to contribute some form of work to help operate the vessel. He was also known to have developed a dislike of shirkers, individuals who did not contribute to the ship's maintenance.
Chegg's home continent of Alanciar lay to the east of Keshtah Minor and the two continents were separated by a vast ocean. Both continents were home to the Keshiri species, a humanoid sapient species that was indigenous to Kesh. In 5000 BBY, the Kesh of Kesthah Minor came under the domination of stranded Human Sith, who became known as the Lost Tribe of Sith. Eventually, several Keshiri from Keshtah Minor including Adari Vaal managed to escape to Alanciar where they warned their fellow Keshiri of the threat posed by the Sith. In response, the Alanciari strengthened their military defenses over the following centuries in order to ward off a potential invasion by the Sith.
In 2975 BBY, the Lost Tribe under the leadership of Grand Lord Varner Hilts invaded Alanciar. Despite initial resistance by the Alanciari, the Sith were able to end Keshiri resistance by using the Alanciari soldier Jogan Halder to convince his people that the Tribe did not actually pose a threat to them. The Sith claimed to be the ancient Protectors who had been prophesied in ancient Keshiri mythology. Lord Hilts and fellow Sith Lord Edell Vrai claimed that the rival Sith Lord Korsin Bentado was a servant of the evil Destructors, demonic beings in Keshiri religion. Thus, the Lost Tribe assumed control over all of Alanciar's peoples, lands, and resources with minimal bloodshed. As a consequence of the Alanciari annexation, the Sith also gained access to Alanciar's timber reserves and mariners.
Following the Sith annexation, Captain Chegg automatically became a subject of the Lost Tribe's empire on Kesh. Following the establishment of regular trade between Keshtah Minor and Alanciar, Chegg and his mariner Southern Star would sail regularly to Keshtah Minor's ports. During these travels, Chegg and his fellow Keshiri came into frequent contact with both the Human Sith and their Keshiri subjects on Keshtah Major. Due to his experiences, Cheggs came to reject the official Sith propaganda that the Human Sith were the mythical Protectors and realized that they were actually mortal beings. The Lost Tribe's government would also send Human slaves to work as sailors aboard these sailing ships. Due to the poor quality and character of these crew, Chegg gradually developed a dislike of humans.
In 2974 BBY, the Lost Tribe sent an exile—the outcast Parlan Spinner—to work aboard the Southern Star. Spinner was a common criminal who perpetrated several acts of mischief against the Lost Tribe government. While he had originally been slated for execution, Grand Lord Hilts had decided to spare his life since he wanted to give the youth another chance to channel his ambitions for more productive purposes. At that time, Chegg's ship was visiting the new docks west of the town of Berav. The Sith authorities had assigned him with the mission of exploring Eshkrene, the southern polar continent. Hilts had embarked on a programme of exploring the unknown lands and seas of Kesh as part of his wider goals of ensuring the long–term survival of his people. The Lost Tribe had recently emerged from nearly a millennia of civil war which had devastated much of Keshtah Minor.
Unknown to Captain Chegg, his crew, or Spinner, the Sith princess Takara Hilts had stowed aboard the Southern Star. Despite her privileged position in Sith society as the Prefect of the Tahv Constabulary, Hilts resented her father's meritocratic system which meant that she could not inherit the office of Grand Lord by virtue of her birth. As with many of her fellow Sith, Takara saw Alanciar as a new frontier that was wealthy, vast, and "full of wonders." She thought that if an outcast like Spinner could make a fresh start in Alanciar, a Sith princess like her would be able to run the place in a month. Unknown to her, Chegg was actually taking the ship on an exploratory mission to Eshkrene.
Takara emerged from her hiding place below deck while Spinner was sharpening his daggers. After Spinner related the true purpose of the Southern Star's voyage, Chegg encountered Takara and quickly realized that she was a stowaway. Spinner tried to explain to Chegg that Takara was actually a Sith princess and the daughter of Grand Lord Hilts. However, Takara claimed that she was merely another passenger and attempted to bully the Keshiri captain into submission by using her privileged position as a member of the Human elites who ruled Kesh. However, Chegg refused to tolerate Takara's insolence and sharply reminded her that the "only gods" on his ship were the surveyors and straw bosses.
Backed by several dagger-wielding Keshiri crew, Chegg reiterated that everyone else aboard the ship were "nothings" and ordered the two Humans to get back to work. The Southern Star was entering uncharted waters and they needed all the available manpower to make a safe landfall. Spinner and Takara were immediately put to work manning the sails. While making landfall, Spinner would criticize Takara for not using her social status to give them an advantage over Captain Chegg and his crew. Takara responded that her parents would not have given her the advantage of using her family status but claimed that she had an escape plan.
Shortly later, the Southern Star safely landed on the frozen shores of Eshkrene. Captain Chegg led a landing party which set up camp in a nearby forest. Chegg and the Keshiri crew regarded Eshkrene as a barren, frigid wasteland and expressed bemusement at why the Lost Tribe had wanted them to survey the South Pole. Chegg even joked about christening this unexplored frontier as the "Frozen Pit." Since a snow storm was approaching, he ordered his men to set up shelters and reminded them to be careful since the wild animals that lived here were unknown to the Keshiri and the Sith.
Meanwhile, Takara and Spinner attempted to sneak aboard the Southern Star while the crew were busy setting up camp and flee to Alanciar. However, Chegg quickly detected them and ordered his crew to kill the two Humans. He also voiced his feelings that he had known that the outcast Spinner was a troublemaker as soon as the Sith had sent him to them. The two Sith were able to use their Force abilities to fight off the Keshiri crew. Meanwhile, Chegg promised to give double rations to whoever killed the ringleader and triple to whoever caught them alive.
Takara and Spinner fled out of the frozen forest onto a frozen plain where they encountered the bones of a large beast. During their flight, Takara dropped her lightsaber which was retrieved by Chegg himself. Chegg and his crew quickly caught up with the two fugitives and prepared to kill them with their hammers and axes. Chegg himself commented that while the Keshiri lacked the Force powers of the Sith, they knew not to lose their weapons in the snow. However before Chegg and his men could lay a hand on the two Humans, they were hit by arrows fired by several hooded figures.
Chegg and crew who had joined the pursuit were all killed in a hail of arrows. The hooded figures later revealed themselves as the Doomed, the descendants of ancient Jedi and Dark Jedi who had also become stranded on Kesh following the Hundred-Year Darkness. The Doomed quickly took the two Human Sith into custody. Other members of the Doomed also detained the remaining members of the Keshiri crew who had landed and impounded the Southern Star. Meanwhile, the dead bodies of Chegg and the other Keshiri pursuers were left to rot on the frozen ground.
Despite his death, Chegg's remaining crew were subsequently able to escape from their Doomed captors with the help of Parlan Spinner. They escaped their poorly-guarded prison and seized back control of the Southern Star, overpowering the Doomed sentries. During their escape, Spinner also stole the Doomed's "Great Weapon": an oubliette containing the hibernating Dark Jedi Baron Remulus Dreypa, one of the Dark Jedi who had survived the Battle of Corbos and helped found the Sith Empire in the Stygian Caldera. He and his followers attempted to return to the Galactic Republic to wreak their vengeance but were thwarted by several Jedi veterans from Corbos.
The Jedi pursued Dreypa's Dark Jedi forces through hyperspace and eventually ended up on the remote planet of Kesh. The Jedi and Dark Jedi had fought on Kesh, triggering the Great Calamity. Eventually, the two parties made peace and migrated to Eshkrene, and became the ancestors of the Doomed. Dreypa was imprisoned within his oubliette. Spinner released Dreypa who unleashed an armed uprising on Kestah Minor with the intent of return to the stars. However, the Sith Lord was defeated through the combined efforts of Spinner and his former enemy Takara Hilts who saved the existence of both the Lost Tribe and the Keshiri of Kesh.
Chegg believed that everyone who came aboard his ship had to work and contribute to the ship's upkeep. He was well-respected by the Alanciari crew aboard his ship Southern Star. As an Alanciari who had grown up before the Sith annexation of Alanciar, he did not share the same fear and reverence that his brethren on Keshtah felt towards their Sith overlords. He resented the attitudes of the Human Sith from the Lost Tribe, who treated the Keshiri people like serfs. The Lost Tribe justified their dominion over the Keshiri by promoting the founding myth that they were the descendants of the divine Skyborn, legendary Keshiri gods who had fought against the evil Otherside eons ago. During to his interactions with Sith slaves, Chegg realized that the Human Sith were not gods and became critical of the Lost Tribe. Ultimately, his dislike of the Sith led to a confrontation with the two Human Sith Spinner and Takara, which ultimately ended in his death.
As the captain of a sailing ship crew, Chegg was skilled in operating a Keshiri mariner and was familiar with the seas around the continents of Keshtah Minor and Alanciar. He was known to carry a knife as a weapon. While he was not Force-sensitive like the Human Sith overlords who ruled Kesh, he and his men still knew how not to lose their weapons in the snow.
Chegg first appeared in Lost Tribe of the Sith—Spiral 1, which was first released on August 8 2012. He was a minor antagonist in the story and was killed off at the beginning of the comic arc. This marks his only appearance in the Expanded Universe. His storyline was developed by John Jackson Miller, who also wrote the Lost Tribe of the Sith novella series. Chegg was drawn by Andrea Mutti, stencilled by Pierluigi Baldassini, and colored by Michael Atiyeh.