Sports figure(s) involved: Charles Barkley
Year: 2008

Charles Barkley is known for his gregarious, don't-give-a-shit attitude during TNT's studio coverage of the NBA, so does it really come as that big a surprise that the former All-Star was caught running a stop sign in 2008 while on his way to go meet up with a prostitute? Oh, and he was also driving under the influence. So yeah, not a great night for Chuck, especially given the fact that he'd announced his candidacy for Alabama's 2014 gubernatorial election just a few months earlier. We'll double-check on this, but we think that sort've stuff usually doesn't look good on any resume.