Exactly my thoughts. He isn't nearly as big as Mike Tyson was, and he's probably dumber. Betting six figures on MMA fights is poor money management. I'll bet that he nets losses of at least in the 1-5 million dollar per year range on gambling alone with bets like that. Toss in a few bad investments, a posse of 100 or so, and the massive decline in boxing interest. Money can go quick.... especially when you go from 50 mil a year to scrapping for promotional money.
Boxing may be in a general decline but Mayweather does the biggest buyrate of the year out of Boxing, MMA, and pro wrestling.
Him and Pacquiao will probably regret never fighting each other though.