Binance, FTX, BitMex, Silk Road founders all went to jail - it’s a huge coin flip.
BitMex didn't go to jail, they all got probation/ankle tag, for not running a clean money org (allegedly no KYC, registering US accounts from offshore, etc.). CZ got caught in the US anti-China panic that also saw the TikTok ban pass Congress with nearly 80(!) votes in the Senate. Silk Road: drug trafficking.
FTX is the closest analog, but by all accounts they did not run a clean operation. What I have read of their operation would have been grounds for charging even if they were trading legal securities.
Seems the through line is if your main business is illegal, you need to run it as if it were going to be legalized tomorrow.