'Compulsive Masturbater and Porn Enthusiast' Kellen Winslow II Shocks Everyone by Pleading Guilty Before His Rape Trial

SourceIn a stunning turn of events on the eve of his second rape trial, former NFL star Kellen Winslow II decided to plead guilty to rape and sexual battery charges here Monday as part of a plea deal that allows him to avoid the possibility of spending the rest of his life in prison.

Winslow, 36, instead faces 12 to 18 years in prison at sentencing scheduled for February. He also will have to pay a $10,000 fine and register as a sex offender for life.

In exchange for those guilty pleas, the trial that was set to begin Monday has been called off and remaining charges have been dropped except for three other guilty verdicts against him from a separate trial in June. Overall, Winslow was found guilty, or pleaded guilty to, sex crimes involving five different women since 2003, including rape, sexual battery and indecent exposure. …

His two guilty pleas Monday related to two different women in alleged incidents 15 years apart. One involved so-called Jane Doe 4, who said he raped her while she was unconscious at a party in 2003, when she was 17 and he was 19. He admitted guilt in that case Monday, as well as felony sexual battery against Jane Doe 1, a 54-year-old hitchhiker, in March 2018. In that case, he admitted touching her in an intimate area while she was restrained for his own sexual pleasure.

Those guilty pleas are in addition to guilty verdicts delivered by a different jury in June. That jury found him guilty of raping a homeless woman in May 2018, exposing himself to a neighbor that same month and engaging in a lewd act against another woman at a local gym in February. Those three women were age 57 or older.

And so ends the criminal career of one of the great public figure monsters of our time. Ordinarily when we’re talking about a guy who’s admitted to sex crimes against five women, including, though not limited to a 54-year-old hitchhiker, a homeless woman and an elderly neighbor who was working in her flower garden, you have to assume there’s more. In Winslow’s case, there is much, much more. Those are just the most prominent shards of ice on his Depravity Iceberg. As I wrote about back in the summer, SI did a report on him that exposed what was under the water:

From his early years in Cleveland (2004-08), to his final NFL season in 2013 with the Jets, Winslow became known to co-workers as a compulsive masturbater and pornography enthusiast, according to two teammates and three former team officials. He could count on having an empty seat next to him on any team flight, due to his ritual of watching hardcore pornography on his portable DVD player, according to those sources. On one occasion, an equipment manager tasked with delivering gear to lockers after hours walked in on Winslow masturbating at his locker, two seats away from the entrance, according to two team officials familiar with the incident.

During road games when the team stayed at a hotel and had a curfew, assistant coaches who performed bed checks reported on multiple occasions finding Winslow watching pornography. When pornography became widely available on mobile phones, he often watched it on his smartphone during meetings, the two former teammates said. … Later on in his career, after being sent to Tampa Bay via trade, Winslow acquired a life-sized silicone mold of a woman’s torso—complete with vagina and anus—to bring with him on road trips, according to one former assistant coach.

I won’t even take a try at figuring out how a guy who had so many advantages in his life could turn out so hideously, deplorably terrible. But no one had life handed to him from a young age the way Winslow Jr. did. He was a child of privilege. His father is a universally beloved icon who changed the position he played. The son followed his cleat steps into the family business and became a blue-chip, can’t-miss TE prospect at Miami. He was one of a record SIX Hurricanes taken in the 1st round of the 2004 draft. He had it all.

Sure, there were reasons to question him. He infamously delivered a pep talk/rant in which he called himself  “a soldier,” which a country that was watching bodies of actual soldiers get off-loaded from cargo planes from Iraq every day was in no mood for. He was told by his coaches to apologize to his teammates, and his apology consisted of him screaming “I ain’t doing it!” and pointing at guys around the room “You loved that shit! And YOU loved that shit! And you!” while his coaches died horrible deaths. Then there was predraft meeting with Joe Gibbs, who had the 5th pick of the draft. Which never happened because Winslow was asleep in his hotel room. He eventually went to the Browns at No. 6.

So he had a stable home, a respected family, talent, fame and money. In life terms, his ball was spotted 1st & goal at his opponents’ 5. And he took it right straight backwards. He had everything except that one drop of humanity you need to not molest a passed out, vulnerable 17-year-old, avoid jerking off in front of a woman trying to work out at the gym and refrain from packing a sex torso in your luggage on road trips. I’m way under-qualified to explain how a guy with all the advantages could turn out so horribly, horribly wrong. That’s for somebody’s doctorate thesis or a book by some PhD. All I know is he’s off the streets for a while. And should he not survive in jail and get back on the streets in 18 years or so, the world will be a better place for it. Good riddance, shithead.