Sports figure(s) involved: Roger Clemens
Year: 2008

Roger Clemens has done a lot of things during his professional career to make people think that he's something of an asshole, but starting an intimate relationship with a 16-year-old girl when he was 28 and married with two kids might be the worst.

According to McCready, the two met in a Florida bar when she was still in the early stages of her career and, though they were close, the sexual part of their relationship didn't begin until a few years later. Whatever the case, The Rocket had a wife and kids. What's he thinking getting involved with someone who can't even legally vote yet? When asked about the situation in 2008, all that Clemens had to say about it was that, "I have made personal mistakes in my life for which I am sorry." You should be a lot more than sorry, dude.