A Wookiee life debt was nothing to be taken lightly, and Chewbacca's to Han Solo was no different. Seeing his partner of so many years encased in carbonite at the hands of the Dark Lord of the Sith and being unable to do anything to stop it had torn the Wookiee, but he had decided to take care of Leia in Han's stead, and that was what he did. He was fond of the Tatooine farmboy as well, but losing him to the Empire did not matter nearly as much as losing Han to Boba Fett. If he could have chased the bounty hunter, he would have, but his responsibility had been to Leia, and getting her to the Falcon was top priority.

Thanks to the skills of the astromech droid, R2-D2, allowed them to escape with their lives, but just barely. During their flight from Bespin, Leia seemed distraught, but Chewbacca had more important things to worry about; he understood her grief at losing Han, but her mind seemed constantly elsewhere, so he left her alone. They met the Rebel Alliance fleet at the rendezous point at Sullust, and began to recover. Chewie and his son, Lowbacca, began formulating a plan to retake Han from Boba Fett before he reached Jabba the Hutt. Unfortunately, their planning session was interrupted by a fleet of Star Destroyers.

The Empire had the jump on the Rebel fleet right from the start; within moments, several key capital ships were crippled, their starfighters still in the docking bays. Fortunately, Chewbacca, Leia, and the droids made it to the Falcon and launched before Home One came under attack. As Rogue Squadron vainly tried to fend of the might of the Imperial Navy, Chewbacca engaged in strafing runs against the capital ships in an attempt to draw their fire away from the capital ships. Luke had led the Empire right to them, and their people were dying because of it. Enraged at the betrayal, Chewbacca engaged in daring, almost reckless attack runs against Star Destroyers at point-blank range. His tactics paid off, but at a horrible cost: Chewie brought the Falcon in close to the Star Destroyer Avenger, dropping a pair of concussion missiles in one of its shield generators, but the YT-1300 took a heavy blow to its dorsal weapons turret, killing Lowbacca and sending the ship careening out of the battle.

Some quick jury-rig repairs allowed a distraught Chewbacca and Leia to escape the battle, but their last vision of the skies above Sullust was of a devastated Rebel space fleet. Most of the star cruisers donated by the Mon Calamari had either been utterly destroyed or floated dead in space, while only the barest remains of the Corellian Corvettes and Nebulon-B cruisers, not to mention the smaller support craft, drifted in the dark silence of the Rebellion's graveyard. Fortunately, a few of the transport vessels managed to make it away from the fight, but whether or not the passengers aboard them survived remained a mystery; certainly, under the strengthened Empire, none would admit to have been aboard a Rebel transport.

For weeks they fled, narrowly escaping the Empire as they hopped from system to system. Returning to Nar Shaddaa, the Wookiee has some old friends repaint the ship and get new transponder codes to buy them some time. Chewbacca held himself responsible for Calrissian's death, but when Leia Organa told him that she would be continuing on without him, he almost worked himself into a fury. In the end, she convinced him of the necessity to go their separate ways, and he gave her the Falcon for the duration of her exile. If he could not be with her to protect her, his ship would. He decided that he would return to his home planet of Kashyyyk and gather up his friends and family capable of leaving the planet to rescue Han. Leia snuck him back onto the planet, unbeknowns to the Imperials, and he stood atop a great wroshyr tree and watched his last ties to Han Solo streak off into the night.

As the months passed, with Chewbacca again with his family and friends, the desire to run off and rescue Han eventually settled down enough for him to make a plan. He would remain on Kashyyyk for long enough to gather a strike force and head back off planet. Only, seeing his family again made him realize how bad things had gotten on Kashyyyk. The constant slave raids by the Trandoshans continued unabataed, even aided by the Empire from time to time, and in the characteristic Wookiee fashion, seeing the oppression Kashyyyk endured only enraged Chewbacca. The strike force he gathered to retake his partner from the clutches of Jabba the Hutt began training by ambushing the Trandoshans as they arrived on the planet. Chewbacca became so engrossed in this struggle against the invaders that time began to pass without his realization.

One positive side to the commando raids he and his band undertook was the training he received. If life on Kashyyyk had been had before, Chewbacca and his comrades underwent harsher rigors and more dangerous assaults than anything the population of the forest planet had ever seen. Chewbacca and his band of liberators struck hard and fast against invaders, from beneath the habitable layers of the trees. They moved like silent ghosts through the trees, striking against their opponents then vanishing under the canopy once more. The Empire's bounty on Chewbacca's head rose as the months passed, but none who approached the planet could get more of a glimpse of him while there. And, if they got that glimpse, they did not live to tell about it. The Liberators became elite even among the other Wookiee warriors, though in the back of his mind, Chewbacca knew that the day he would be forced to leave his planet and fulfill his life debt was close at hand.

That day came much sooner than he could have anticipated when the Falcon appeared in the skies above Kashyyyk. It was the Princess, returning at last from her exile. It did not affect Chewie to find that Leia had become a Jedi Knight--the tales of their deeds were well-known in Wookiee culture--but her offer to return the ship to him reminded him of his duty to Han. He gathered the Liberators, and prepared to leave the planet as soon as possible. Equipment was gathered, goodbyes were said, and the ship was loaded. Chewbacca and his Liberators had no idea that these goodbyes would be their last.

As the ship picked up off the planet, terror siezed the crew of the Falcon as death appeared in the skies above Kashyyyk. The Darksabre, under the command of former-ally Luke Skywalker, had followed Leia on her trip to return the ship. Poised over the jungle planet, the Darksabre commenced primary ignition just as the Falcon lifted off, and rained destruction down on the planet. As the powerful superlaser cracked the crust of the planet, thousands of kilometers of forest were flash-fried before the superheated core of Kashyyyk detonated, blasting the Wookiee homeworld into ruins. Leia, Chewie, and the Liberators were hurled through space by the explosion; it was a miracle, or perhaps the will of the Force, but the Falcon 's hull remained intact, though severely damaged. The Empire left Kashyyyk victorious, but never suspected that their true targets survived.

The Liberators were devastated. Their homeworld gone, the only thing that had saved them was their mission to save Han Solo. Some blamed Leia for the attack; others took it as confirmation that the mission to rescue Han was that much more important now that their homeworld was gone. The ship limped back to Nar Shaddaa for repairs, where half of the crew abandoned the mission to seek retribution for the crimes of the Empire against the Wookiees. Even those who blamed Leia for bringing the Darksabre to Kashyyyk did not go so far as to do more than voice their opinions. Chewbacca was still fiercely loyal to the Jedi Knight, and would not allow any of the others to seek their revenge on the woman. As the Liberators scattered, Chewbacca's hope for rescuing Han began to wane. In the years that followed, the Liberators became bounty hunters, commandos, bodyguards, and one even became a Jedi Knight in Leia's future Order. Some of the elite commandos sought out other Wookiees who were off-planet during its destruction and began to train them in their special combat techniques and tactice, expanding the Liberators' numbers and freeing many of the slaves.

Chewbacca remained on Nar Shaddaa for a while, working at his old trade as a smuggler, all the while cultivating contacts that kept him apprised of the situation on Tatooine. He slowly began to develop a plan to rescue his partner alone, but every time he did so he saw another flaw, then another, until it seemed as though he could not possibly recue his comrade. The Falcon , repainted, modified with a new sensor profile, and with new transponder codes, kept its reputation as the fastest ship in the Galaxy, even though the title meant little to Chewbacca if his partner wasn't there to brag about it. He occasionally sent messages to Leia, consulting her opinion on his plans, but never more than once every few months.

When a Jedi Knight named Mara Jade contacted him years later, he thought his luck might have changed. Sent to him by Master Organa, the woman was prepared to help him infiltrate Jabba the Hutt's palace, though he thought that perhaps she would rather not have been given the assignment. Still, after a few scrapes on Nar Shaddaa, Chewie became convinced that she did have the necessary skills to help him get Han Solo out of captivity. Together, they worked out a plan to rescue the smuggler who had spent many long years in carbonite.

Using forged documents and a stolen ship, Mara and Chewie arrived on Tatooine in the guise of bounty hunters seeking employ under Jabba the Hutt. They timed it so that Jabba would be off-world, visiting his family during one of the clan's grand meetings, so they would only have a few lackeys to deal with. Unfortunately, the Hutt crimelord returned early from his trip, interrupting their plans to free Han from captivity. When things got ugly, a lightfight broke out right in Jabba's throne room, with Chewbacca and Mara fighting for their lives against Jabba's entourage. Chewbacca tried to bluff his way out with a thermal detonator--only, Mara wasn't bluffing. The resulting explosion decimated Jabba's palace, killing the crimelord and destroying Han Solo's carbonite slab, and it was only Mara's talent with the Force that saved the pair from certain destruction.

Following the debacle on Tatooine, Chewbacca sank into a slump that he never fully recovered from until many years later. He could not return to Nar Shaddaa, for the price on his head was too high. He learned of an enclave of Wookiees that had taken up residence on Ithor, amongst the jungles of the planet, and moved there to rejoin his kind.

When Leia called upon him many years later, Chewbacca was wary until he heard the target. Rumors had been spreading that the Empire was at war with some invaders, perhaps from the Unknown Regions, though no one could say for sure. Gathering up the few Liberators he kept in touch with, he prepared to help avenge the destruction of his homeworld by engaging in a suicide assault on the Darksabre. The team consisted of Master Leia Organa, Chewbacca, ex-Liberator turned Jedi Knight Durrawar, Liberator commander Rorworr, and a handful of other Liberators who saw the mission as their final chance for revenge upon the ship that destroyed their home.

As Leia sought out Lord Vader, the Wookiee Liberators made their way towards the ship's core. Stealthily traveling through the corridors, they took advantage of the Imperials' distraction at the battle raging in space to slip nearly unnoticed past security. Eventually, they reached their destination, and placed the explosives on the ship's main reactor. Unfortunately, they could not do so unnoticed, and found themselves fighting their way back to the Falcon , securely attached to the hull of the Darksabre where they were to rendezvous with Master Organa. Durrawar made the ultimate sacrifice, holding off stormtroopers with his yellow-bladed lightsaber as Chewie and the others made their escape. Rorworr and three others fell to blaster fire in an ambush just outside their ship, and it was only Leia's talent with the Force that allowed them to regain entry to the Falcon . As they sped away, reduced to Leia, Chewbacca, and two other Liberators, the Darksabre erupted into a ball of fire several kilometers long. Finally, the Wookiees had their retribution for the destruction of Kashyyyk. The war was not over, though, and Chewbacca knew it.