John McEnroe

McEnroe played in the Davis Cup the year he retired from the game, but 1992 was his last time as a playing member of the team. Throughout the 1990s he pled his case for the head coaching spot, but he was repeatedly turned down. In typical McEnroe fashion, he blamed the U.S. Tennis Association, telling Sports Illustrated that, "If they want somebody who is going to suck up to the suits, they're never going to give it to me."

But they did give it to him in 2000, after years of pressure. It proved to be an unwise choice. According to Jon Wertheim of Sports Illustrated, "When he finally got the job, he alienated the top American players, trashed opposing athletes and coaches and blew off meetings and press conferences." At one point he even "showed up at a captains breakfast in a bathrobe." McEnroe quit as Davis Cup coach within a year.