Although his species hates wookies, the reptilian bounty hunter name Bossk hates one wookie in particular. Chewbacca and his Corellian friend Han Solo have humiliated Bossk too many times, and he means one day to have his revenge.
Bossk is a Trandoshan, a three-toed, three-fingered reptilian. Like the rest of his species, he has the ability to regenerate lost limbs and can see in the dark by using the portion of his eyes that responds to infrared light. His home planet is in the same solar system as Kashyyyk, the Wookie homeworld. Bossk hates the hairy beasts, as do most of the Trandoshans. The Wookies owe much of their pain to the Trandoshans. The reptiles used to hunt them, skinning them for their pelts. But the worst transgression came when a Trandoshan dignitary convinced the Empire to use Wookies as their slave labor. After the Empire subjugated, enslaved, and occupied much of Kashyyyk, the Trandoshans offered to hunt down any Wookies that had escaped.
When his liege lord suggested that he become a bounty hunter who specialized in Wookie captures and kills, Bossk was more than happy to do so. He outfitted himself with protective body armor and a variety of weapons. His favorite weapon was his blaster rifle, which hung from an elaborate sling fastened around his neck and under his left arm. Bossk gained great fame for his success in hunting Wookies, but his most wanted target persistently refused to present himself. A giant named Chewbacca - allied with a Corellian smuggler named Han Solo - had gained a high amount of respect in the galaxy's underworld, and Bossk decided to bring him down. Meanwhile, he continued the hunts, and in addition to the many Wookies he trapped and killed, he made twelve captures, delivering eight to their enemies alive.
Finally, Bossk got his shot at Chewbacca. He had heard news that a group of renegade Wookies had set up a safe colony on Gandolo IV, a remote Outer Rim world. The Trandoshan went to the Imperia governer of the sector, to be paid in advance, and then he armed himself for the trip to Gandolo IV. There, he found his prey. Chewbacca was helping the small group of Wookies settle on the rocky moon. Bossk and his thugs surrounded the Wookie camp, outnumbering and easily capturing the poorly armed creatures. Bossk had little time to gloat over his victory, though, as Chewbacca was not alone. Han Solo had dropped has copilot on Gandolo IV, then he visited an old girlfriend in a nearby system. Now he returned, the Millenium Falcon's scanners picking up the bounty hunter ships even before he got in visual range. Solo drove the Falcon toward the planet, catching Bossk and his thugs by surprise, as they had the Wookies. Solo flew low over the colony, buzzing the hunters and strafing the ground with laser fire. He couldn't hit the bounty hunters full on, as they had the bound Wookies in their midst. Intending to pursue the Falcon, Bossk and his thugs boarded their own ship, leaving two guards behind. But Han Solo had other plans. As soon as the entry ramp was raised on Bossk's ship, Han pulled the Falcon directly above it, lowered the landing gear, and touched down directly on top of the other ship! The hunter's craft buckled under the strain, its own landing gear caving in, its hydraulics shot, and its interiors sparking and exploding. Bossk's people tried in vain to get the emergency hatches open. Meanwhile, Chewbacca and the other Wookies broke free of their binders and overcame the two guards. Chewbacca and Solo agreed to help the Wookies find a new, safe colony, refusing to kill the humiliated Bossk before they left. The hunters finally freed themselves from the crushed shell that had been their ship; it had taken them days to cut their way out with blasters and a few hand torches. A week later, the group was picked up by a small out-world hauler carrying a load of nerf manure.
Years later, Bossk would get another chance at the Wookie and the brash Corellian. Shortly before the Battle of Hoth, Boba Fett gathered several fellow bounty hunters, including Bossk, Dengar, and a newer hunter named Skorr, to find Han Solo. They captured him, along with Luke Skywalker and Chewbacca, aboard the pirate Raskar's ship. Bringing the Rebels to the planet Ord Mantell, the hunters were taken by surprise when Luke used his Force powers to engineer the trio's escape. When Darth Vader put out an open call for bounty hunters to find the Millenium Falcon, Bossk immediately went to the Super Star Destroyer Executor. There, he found he had competition from five other bounty hunters: Boba Fett, IG-88, Dengar, Zuckuss, and 4-LOM. Thinking he had the inside track on where the Falcon was located, Bossk took off with some temporary partners - bounty hunters who hadn't made Vader's cut. Much later, Bossk found out that Boba Fett had indeed succeeded in tracking the Falcon and in procuring the carbon-frozen body of Han Solo to deliver to Jabba the Hutt. Chewbacca had escaped, though, aided by the Baron Administrator of Bespin's Cloud City.
Following the Alliance's daring mission to rescue Han Solo on Tatooine, Bossk and IG-88 moved on to the hunter's world of Keyorin, where they accepted bounty from the small-time crime boss, Drebble, for Lando Calrissian's head. Coincidentally, Lando had accompanied Han and Chewbacca to Keyorin. A confrontation soon followed, but the Alliance heroes were victorious yet again.
Now fifty-eight standard years old, Bossk is willing to sacrifice Chewbacca's pelt for a quick kill if he ever sees the Wookie again. Meanwhile, there is a whole galaxy of bounties to pursue, and Bossk is just the Trandoshan to collect.