Doole's career on Kessel began as a spice mine administrator. He engaged in corrupt practices, arranging deals for various smuggling organizations, particularly by illicitly selling glitterstim shipments to the Hutts. Hewat, an officer with Imperial Customs, sought to expose Doole's illegal spice distribution network. During his time working for Jabba the Hutt, Han Solo frequently visited Kessel to smuggle spice. Doole, a glitterstim user, exploited its effects to amplify his mental capabilities. However, excessive glitterstim consumption induced paranoia, leading him to become excessively suspicious of Solo. Consequently, Doole informed the Imperials about Solo's activities. This infuriated Jabba the Hutt, who plotted to assassinate him. Doole begged Jabba's enforcers to take only his eye, which they did, although they would have inflicted further harm had Arb Skynxnex not intervened and eliminated them.
Following Palpatine's demise at Endor in 4 ABY, Doole initiated an uprising against Imperial control of Kessel, successfully seizing control of the planet by overthrowing the guards. Subsequently, he appointed Skynxnex as his second-in-command. In the aftermath of the revolt, Doole discovered a deceased rancor in the prison, which had perished from starvation. He lamented the creature's fate and the disruption of his plans to feed Imperials to it. While he dispatched them to the mines, he subjected the former head of the prison to torture and encased him in carbonite, displaying the man's mummified remains in his office. Around 5 ABY, Doole was also responsible for the deaths of Kyp Durron's parents, an action that would later have dire consequences for him.
Having solidified his authority, Doole arranged for numerous female Rybets to be transported to Kessel for the purpose of exclusive mating. He exploited his offspring as a source of inexpensive labor during their larval stage before ultimately killing them. As a consequence of the murder of their children, his concubines harbored intense animosity towards him.
In 6 ABY, Doole negotiated a deal with Wedge Antilles and Rogue Squadron concerning prisoners under his custody. Doole agreed to release various political prisoners captured during the height of the Galactic Civil War in exchange for Antilles removing several "problem prisoners" from Doole's care. Through this arrangement, Doole divested himself of several influential Black Sun members, such as Zekka Thyne and Fliry Vorru. Although Arb Skynxnex was at the top of the list, Doole adamantly refused to release him. Rogue Squadron inflicted significant damage to Kessel's defenses during the mission, prompting Doole to prioritize the construction of a fleet to safeguard the planet.
In 11 ABY, Han Solo and Chewbacca were dispatched on a mission to Kessel to reestablish relations with the planet and potentially negotiate the release of any remaining political prisoners. Upon encountering Doole's fleet, Han Solo transmitted a greeting, but his ship was shot down, and he was taken into custody. Initially intending to execute him, Doole instead imprisoned him in the mines. When Leia Organa Solo began searching for her husband, Doole sent Skynxnex to assassinate Solo and Chewbacca. However, they were already planning an escape and fled in a shuttle to The Maw, accompanied by a new ally named Kyp Durron. Skynxnex met his demise when he was killed and consumed by a Spice spider.
Leia dispatched Luke Skywalker and Lando Calrissian to Kessel to ascertain Han's whereabouts. Calrissian posed as a prospective investor, while Luke acted as his assistant. During a tour, they observed a repaired Millennium Falcon alongside Doole's fleet. They reclaimed the ship and fled the planet. Simultaneously, Admiral Daala's contingent of Star Destroyers from the clandestine Maw Installation appeared, pursuing the Sun Crusher. Mistaking Doole's fleet for a Rebel trap, she engaged the fleet in battle, resulting in its destruction.
Chewbacca addressed the Galactic Senate, proposing a mission to liberate prisoners on Kessel and within the Maw Installation. A fleet was deployed, and New Republic forces attempted to apprehend Doole. However, upon the release of his concubines and children, they pursued him into the mines, where, like Skynxnex, he was attacked, killed, and devoured by numerous energy spiders.