Every day he knocks back bottles of rum, wanders the mangrove islands, and gambles. (Sometimes he ends up in some tight situations because he needs some kind of fun post-retirement.) It's easier to deal with… everything when alcohol is pumping through his blood than with a clear head.
When his head is clear, all the memories and feelings and thoughts he's held onto for twenty years come crashing down. He starts thinking he should've gone to Loguetown to say his final goodbye.
But then he remembers putting all his God-deserved faith into the last words of his best friend.
And then he laughs and motions for Shakky to pour him another glass of rum.
When should you ever trust the words of a pirate?