Sports figure(s) involved: Denny Neagle
Year: 2004, 2006

When athletes fall from grace, they fall hard. Just look at Denny Neagle, the former All-Star pitcher who was caught soliciting sex from a prostitute in both 2004 and 2006 after his career slowed down due to injuries and age. After getting ticketed in 2004, the Colorado Rockies voided the final year of his contract, and Neagle's wife left him. To be honest, it's understating the situation to call that just a fall from grace. That's more like belly-flopping off the Empire State building.