- I get that Rocky's accountant stole all his money and left him penniless and his injuries forced him to retire, but we are still talking about (in-universe) the most popular athlete in the world (and probably the most popular person alive). All he would need to do is make a couple appearances and autograph sessions and he should be well on his way to recouping his lost fortune.
- Judging by Rocky II, I always thought Rocky was quite uncomfortable with the media-circus aspects of the fight game. He'd probably prefer to just be a coach, where he doesn't really need to be in the public eye and can still be fairly hands-on with the sport he loves, rather than being a pop-culture figure.
- It would make sense that, as the Balboas' former accountant was being taken to court, that they would see some of that money returned to them. Not immediately, but in between the fifth and sixth films.
- Rocky Balboa does reveal that he had raised enough capital to open a restaurant. Perhaps a few public appearances was how he got funding.
- Rocky's past as a loan shark's enforcer got revealed and he suffered a severe blow to his popularity which prevented him from doing public appearances. Like in real life, it seemed this initial scandal didn't actually affect his long term popularity. After it blew over, Rocky probably didn't have any serious financial issues thereafter.
- The beginning of the film shows that the younger boxer, Union Cane, and promoter George Washington Duke, want to challenge Rocky for a heavyweight championship...that Rocky gave up in Rocky IV to fight Ivan Drago. Even if Rocky was still champion after returning from Russia, his brain damage diagnosis would be enough (at the time) to strip him of his boxing licenses and heavyweight championship. So, the main reason George Washington Duke wants a boxer to fight Rocky is for...prestige?
- Considering Duke's role as a shady, money-hungry promoter, he'd likely look for any way to spin it to make the most money from a fight. Something like about 'the true heavyweight champion' or something.
- Also, Cane, derided as a "paper champion", would be beating the Champ who never legitimately lost the title, not to mention one of the most universally heralded champions of all time. That would go a long way towards garnering Cane some legitimacy himself, as well as no small amount of respect.
Headscratchers / Rocky V