It's always crappy opsec that gets people otherwise very savvy.
Kinda like how the big mastermind criminals like Capone get away with murder and racketeering but get fucked on tax evasion.
Reading this guy's posts, his ego is the biggest issue, and it will be his downfall. The "I literally can't get caught" mentality inevitably leads to carelessness and blabbermouthing.
That’s a little different. It wasn’t that Capone couldn’t handle taxes, it was that until that point nobody used it as a serious mechanism to take town criminals. It was only validated as a good approach by the Supreme Court a few years before. In fact, one of the primary pieces of evidence of his tax evasion were from communications from his lawyer about how much tax to pay to make his tax history legit in light of the recent effectiveness of tax convictions.
Now major criminals launder money to avoid that.
It appears the government at times invents laws so they can go after criminal gangs (see RICO)