Best Sports Enigma Fort Lauderdale and Palm Beach 2008 - Pat Riley
He's a legend — and a loser. Subtract the championship year, when he took over the Heat from Stan Van Gundy, and Pat Riley has had an atrocious decade. Subtract Dwyane Wade's heroics in 2006 and Riley hasn't won a playoff series in this century. He's coached some of the best players the world has seen, yet he makes amateurish personnel decisions (Ricky Davis? Jason Williams? Are you kidding?). With all his early success with the Lakers, Riley earned the right to relax, yet he seemed to get tenser each season. And with good reason: This year he managed to put one of the worst teams in league history on the floor. It was so bad that he fired himself (for the second time). Yet even as he showed his flaws as a coach, he earned our respect. Night after night he was courtside coaching his terrible team like the playoffs were at stake. He went down with the sinking ship. And for that we give a tip of the hat to a man we'll never quite understand.