23. Nate Newton
Newton is one of the most colorful characters on this list. The former NFL guard played 198 games for the likes of the Tampa Bay Buccaneers and the Dallas Cowboys. However, that’s not the full story. Newton was a massive individual, weighing a hefty 335 pounds at his athletic prime. But this larger-than-life figure wasn’t always in shape.

In short, the three-time Super Bowl winner had massive problems with his diet. He once weighed up to 411 lbs and had to have a gastrectomy. Furthermore, he ran into problems with the law. Newton was the ringleader of a dog-fighting ring. He owned 14 pit bulls bred for this purpose. The Florida native also spent time in jail for drug trafficking.