system
A chat on subreddit /r/wallstreetbets
human
&gt;How did SBF not realize. Dude is dense as lead.

Honest speculation from my side: If you're sufficiently rich the gray areas of the law are a lot wider than for the rest of us. It's ENTIRELY possible he really thought he was enough inside the gray area to not be in danger of being prosecuted for any wrongdoings.  

Having a lot of money opens up a whole wide area of possibilities of being a "smart business man" beyond the "everything past this legal limit is illegal" line that is the reality for the rest of us.
gpt
if crypto kept going up forever he would have been fine.  (bold strategy!)