José Mourinho

José Mourinho boasts a 66% win rate across five leagues — better than #6 Serena Williams' 85% in tennis — yet his 2011 eye-gouging attack on Barcelona's Tito Vilanova drew a five-match ban and a €20,000 fine. He's been sacked from 60% of his managerial positions, including Chelsea twice, after spending an average of 2.8 years per club. Mourinho's reign as the Special One outlasts #7's typical tenure by 1.1 years, but his habit of burning bridges makes #5 Mike Tyson's comebacks seem harmonious.