Han is gambling with his pal Lando again. Chewie can't believe it. His buddy is insane, always taking risks they both know he can't afford. How many worlds have they already been banned from, which by the way is a terrible way to operate for smugglers? Then again, as Han says it, if you're able to do something legally in this business, you're not doing it right...
Well, the good news is that they just won themselves a ship. As far as Chewie can tell, it's a piece of junk. In fact, that's exactly what everyone says when they see it for the first time. The exact words. Every single time. Sometimes he howls in general protest, apropos of nothing, and Han just shrugs his shoulders. What else are they going to do?
Han works on the ship every chance he gets. This turns out to be a terrible development. When they first met Chewie could get him to play games with him. It's a relaxing change of pace for Chewie, playing games. They don't have those on Kashyyyk. Everything's a matter of life and death! That's why he was so happy to leave his home planet behind. Because while Han seems to live his life that way, it's all a con.
Usually, he knows exactly what he's doing. Everything's a calculated risk.
Since that damn ship, however, he seems to have forgotten that a little, always trying to justify the ship. He lost Lando as a friend because of it. Doesn't matter! Entered the Kessel Run, never stops boasting about it, even though it makes no sense to anyone who's never participated in it, like podracing or death sticks.
It should be noted that although he pretends otherwise, Han is a lousy engineer. Just don't tell him so. Chewie learned that the hard way.
After being forced to sign a contract with Jabba the Hutt, they find themselves hanging out on Tatooine, which would not be Chewie's first choice. He hates it there, especially the collection of freaks at Mos Eisley. So he spends all his time trying to negotiate side deals with desperate travelers. That's how he meets Obi-Wan Kenobi. Han won't have any of it, when Chewie tries explaining the situation to him. There are two things that are otherwise really important to the galaxy Han doesn't concern himself with: the Empire and the Force. He's part of a generation that thinks it can pretend neither exists.
This, by the way, is why Chewie has such horrible migraines.
Turns out, as Chewie suspected, getting Han to talk to this guy was worth the risk. His buddy takes the job as a matter of defiance. He doesn't believe any of the old man's nonsense (so Han describes it), but sooner than even Chewie thought they're deeply embroiled in everything they previously tried to avoid. Sure, Han is also trying to avoid the ramifications of burning Jabba the Hutt, but he's finally found a con even he can't handle. A perfect con. Perfect faith in something. Some kind of con.
So Kenobi and his young ally and their two droids lead Han to a princess, with whom he falls immediately in love and succeeds in convincing both of them that this is not really happening, and Chewie finally starts unwinding. Maybe that damn ship paid off after all. Lando ends up in their crosshairs again. Han ends up in carbon freeze, but they get him out of it (eventually), everyone becomes heroes, and Chewie gets to rest easy, fly casual for the first time in ages.
Until he meets the kids. And then all hell breaks loose again!