89. $50,000 Twitter Conversation

Who: Denny Hamlin, NASCAR
Offending Tweet: @dennyhamlin: "Truthfully I don't think It matters to the fans who wins the race as long as its a good "show". Even if it comes as the expense of competition"
Date: July 2010
Consequence: Reportedly fined $50,000

If you're a professional athlete, the quickest way to lose a ton of dough is to imply that your league is fixed and the easiest way to do that is on Twitter. According to Hamlin, he was just trying to have an open debate on ways to improve racing. Unfortunately for him, NASCAR didn't see it the same way and hit him for 50 stacks.