I think it's kind of crazy to play for $ regardless of who you are or who you're playing. A few years back even a GM (Garompon/Pablo Zarnicki) was busted cheating in the Dos Hermanas online tournament. And he was a super active vendor/coach on ICC meaning he had a whole lot to lose.
His current finger notes are kind of amusing:
1: Pablo Zarnicki
2: I challenge any chess player to play Heads Up on Poker.
3: I challenge any poker player to play chess.
4: Former World Ch Junior in chess
5: Actual World Ch on line Poker in NL 6 Max
6: Course of chess lessons 5K 10 hours
7: Course of Poker lessons 10K 10 hours
Countdown til a vehement defender of Zarnicki's honor appears.