
34. The Massage
Technically fans didn’t actually see this, but they can’t unsee the image that it created in everybody’s minds. Police arrested Patriots’ owner Robert Kraft for allegedly soliciting sex at an Asian Massage Parlor in Florida. Prosecutors alleged that the offense occurred at the Orchids of Asia Day Spa in Jupiter, but they dropped the case. However, a court forced the masseuses to pay thousands of dollars in fines.

This was an immensely embarrassing incident for one of the NFL’s most visible owners. The Patriots are the most successful franchise of the 21st century, but this brings the spotlight with it. Nobody wants to see their face all over the news and the internet in connection to this kind of incident. Especially, a billionaire with children and a relationship. There are some things that money can’t chase away.