I'd throw that under the Roger Is A Liar umbrella but point taken.Telling your boss "Please call me and say I'm in trouble. I dare you" sure counts as controversial.
(Though, interestingly, Bill now says in the HR piece that he was trying to take a shot at the NFL there, not at the ESPN hierarchy.)
Most of his time at ESPN and in general has been spent on NBA Value columns, re-telling Teen Wolf jokes and picking against the NFL spread. Considering the size of his audience and his overall media influence I'd say he's been anything but controversial.