Imagine if you were high or intoxicated multiple hours a day, while surrounded by snakes. Now imagine all the scams and little bullshyt schemes your homies could pull on you. "Hey blood, sign this shyt" or "ayo this is the paperwork I told you about fam" while you high as shyt. For 15 years.
Then add on top of that you signed to Birdman and you aren't involved at all with contract stuff. He's the boss and you sign off on what he says. Between shady homies, Birdman, legal fees, drugs, and studio time he's probably broke as fukk and the majority of the fault is his.
The new generation of big rappers are smarter. Drake got his own studio, TDE/Kendrick got their own studio, I'm pretty sure Cole does too. All three are sober most of the day. Nicki has her own business team handling various things for her. It's not surprising all four are better off, even if all four signed bad contracts initially.