27. Bill Belichick
A serial winner with the New England Patriots, Belichick is also a master of the dark arts. His teams were embroiled in numerous scandals over the years. Meanwhile, Belichick was also in the middle of them. The most notorious was in 2007 after the SpyGate saga. The Patriots lost a first-round pick while Belichick received a $500,000 fine. This was because the Patriots secretly videotaped the Jets’ sideline during a game.
Of course, this was an illegal thing to put in place. Nor was it the first time that Belichick encouraged this practice. Then there was the DeflateGate scandal. But Belichick threw Tom Brady under the bus for that one. As a result, Belichick’s reputation is one of the shadiest in the sport. Opponents accused his teams of bugging their locker room and interfering with their radio waves.