[NewYorkDoctorD]

Interesting topic. And look who starts off the list:

20) Jennifer Capriati: This is more of a tragedy than anything.Capriati was a nice girl. I met her many times on the junior tennis circuit. The real Capriati was just as bubbly as the one we saw on camera. But her horror of a dad was always looming. He smothered her, made her hate the game, and turn to other vices.Drug binges and shoplifting charges were part of the fall, although she successfully came back and won Grand Slams again and reached No. 1 in the world in 2001, so she's low on this list. Thankfully, it appears that she's stayed away from her dark side. Capriati appeared on the ABC reality show "The Superstars" last summer and looked healthy.

19) Tiger Woods: Tiger went from this image of the perfect dad with the perfect wife and the $1 billion bank account to the star of TMZ. He reportedly admitted to sleeping with more than 120 women. And now he may surrender the biggest divorce settlement in sports history. Then there's the golf. Nobody wants him to win anymore. We're all just waiting for the next meltdown. So far, Tiger's obliging. He's No. 19 because even if he loses half of his fortune, the dude could still buy the Yankees.

18) Bjorn Borg: Borg won a staggering 11 of the 27 Grand Slams he played, including five Wimbledons. He was the dude's dude, living the dream of celebrity and sport in the '70s.
Then, he walked away from the game, on top, with homes in all parts of the world and as owner of his own island. But after a divorce, a bastard child, rumored drug overdoses and a suicide attempt (which he denies to this day), Borg was on the verge of bankruptcy in 2006 and plans were even made to auction off his Wimbledon trophies. Instead, he created a fashion label that is the second-biggest clothing company in his home Sweden. He also attempted comebacks, but they never equaled the original. All in all, Borg has steadied the ship and is once again enjoying his place as tennis royalty—including the lovely ladies that come with it.

17) Ben Roethlesberger: I'm fresh out of jokes here. The only reason he's not higher on the list is because I don't think he's bottomed-out yet. Dude needs to grow up. Fast. You're not all that, Big Ben. Heck, you can't even get comped at Pittsburgh bars anymore because you're such a douche.

16) Plaxico Burress: I still don't get it. Was Plaxico really that much of a badass that he thought he was going to get shot up at the club? Again, there's a next chapter here. We've seen the fall, but if society holds true, Burress is going to get his shot at a comeback.

15) Michael Vick: He lived the life of a $100 million quarterback in the ATL. Who wouldn't if they were Mike Vick? Ultimately, his backwoods upbringing sank him. I had some pretty sick pictures of dogs I was going to put here, but that would just be gratuitous and pig-piling.
Add in the bad investments and frivolous spending, and you had a morally and financially bankrupt mess. We all want to believe he's rehabilitated. I'll believe it after he starts somewhere for a whole season. Once he gets a taste of the good life again, how will he handle it?

14) Art Schlichter: He was a four-year starter at Ohio State and the last starting quarterback under Woody Hayes. Everybody loved Art, including the Colts. They drafted him fourth in the 1982 draft and thought he was the future. Little did they know about his past. Schlichter was a compulsive, degenerate gambler. He was on the mafia hit list so deep that he went to the FBI for protection. The once-great QB was suspended in 1983 for gambling. He returned in 1984, but admitted to gambling during his suspension. He was released five games into the 1985 season. More gambling arrests followed in 1987, followed by a brief stint in the Arena Football League and a sports radio gig in Cincinnati in the '90s.
He was most recently released from prison in 2006.

13) Lawrence Taylor: Dude. "I thought she was 19," is not exactly going to win you any sympathy. I don't know. Maybe he's just bored. Maybe the straight and narrow just isn't his bag. We're partially to blame. We liked the badass LT. We read the memoir where he bragged about all the drugs and the loose living. This time, it's on you, LT. He fell a lot farther in his personal life than he ever did in the public eye. He made the Hall of Fame and we never stopped liking him.

12) Roger Clemens: There was no argument. Some folks wanted to say Greg Maddux and time has told us that might be true. But, before steroids, Roger Clemens was the greatest pitcher of our generation. Dude was even reportedly there to watch his wife get injected with HGH for this photo shoot. Now, the affair allegations won't stop. And, Clemens still says that he never took any PEDs, though Brian McNamee says he has the goods to finally make him admit it. There's also rumors from a mistress about a sex tape. Rocket Man, you are a world-class letdown. We all know what you are. Again, it's too late for public redemption for you.

11) Ryan Leaf: JaMarcus Russell might be on his way to rescuing you from the title of biggest NFL flop of all time. Just kidding. That's not possible—though I think we only dump on Leaf so badly because we were so ridiculously stupid for thinking that Leaf and Manning were in the same talent league. Leaf's done plenty to pile on his own grave, with prescription drug addictions and stupid arrests. He's on the road to redemption again now, hoping to be an example of hitting your lowest lows and still picking yourself up. For once, we might actually root for this guy.