Maybe... I'd rather do the time, and when I get out a millionaire then do the time and when I get out flat broke.

You won't be able to legitimately cash it out, you'll be imprisoned again for money laundering.

So you'll need to take your winnings to a third world country and generally watch your back.

I'm guessing he had no plan to "legitimately" cash it out ever, given the way it was procured?

Still, he could have tumbled it, traded for Monero, etc. when he got out.

What are you basing any of that on? There are a lot of places to go and a lot of ways to use cryptocurrency. Why would someone be 'watching their back'?