Phil Jackson, New York Knicks
We all know how beleaguered the hapless New York Knicks are, but there was a time when Phil Jackson was heralded as a savior. When the former Chicago Bulls and Los Angeles Lakers mastermind headed to Madison Square Garden in 2014, he signed a big fat five-year contract worth $60 million, with many hoping he'd be able to turn the team around. Yet despite Jackson's involvement, the Knicks have continued to spiral out of control and suddenly that $60 million seems like a big fat waste. Regardless, Knicks owner James Dolan defended his contract with Jackson earlier this year during an interview with sportscaster Michael Kay. "Three years ago, I signed a contract with Phil Jackson – the man who has more championship rings, as far as I know, than anybody else," he noted. "He was the best guy we thought we could find to run the New York Knicks, and I made an agreement with him, and the agreement didn't say that you have to have this amount of wins by this time or anything of the sort." Well, okay then!