Kellen Winslow jnr and his sordid double life away from NFL

Details of former Cleveland Browns tight end’s convictions have emerged in court

Jane Doe was 58-years-old, homeless, and spending most nights sleeping behind the train tracks in the California town of Encinitas. She liked to lie down against the wall there so the sheriffs might not spot her, all of her worldly possessions contained in plastic bags she clutched tight. That was her life when she was befriended by a stranger who often rolled up in his Hummer 2 to talk to her and other transient women. She knew him only as Kevin.

Over several months, he bought her coffee, and food and gave her lifts. Random acts of kindness that gained the trust of a lonely woman at her lowest ebb. Then, on Mother's Day last year, he offered her money for sex. After she refused, he drove to a secluded road in the San Elijo Lagoon, choked, raped and threatened to kill her. Kevin's real name was Kellen Winslow jnr. Six foot five and weighing in at 18 stone, he was 34-years-old and a former NFL tight end with career earnings estimated to be close to $43m.

In his best season with the Cleveland Browns, Winslow caught 82 receptions for 1,106 yards and made it to the 2007 Pro Bowl. The type of campaign that finally confirmed he could make the leap from blue-chip collegiate prospect at the University of Miami to Sunday starter. By that point in his career, he was also somebody team-mates did not want to sit next to on cross-country flights because he invariably spent those journeys watching hardcore pornography on a DVD player. Neither did they want to share a hotel room with him due to the constant diet of adult movies and his chronic masturbation habit.

Nine years

In a California court earlier this month, Winslow was convicted of rape, indecent exposure (flashing a woman working in her garden) and lewd conduct (masturbating in front of a 78-year-old as she exercised at a Crunch Fitness gym). Crimes for which he is likely to be sentenced to at least nine years in prison. After the jury failed to reach unanimous verdicts on eight other charges, including two counts of felony rape and one of kidnapping, the San Diego District Attorney announced her intention to retry each of those next September. Another guilty verdict then could lead to him spending the rest of his life behind bars.


Following a disturbing three-week trial covered live by Court TV, there is little we do not know now about the proclivities (his Internet search history was full of elder porn) of somebody groomed for stardom from his early teens. The son of an NFL Hall of Famer whose name he shares, Wilmslow was grid-iron royalty and knew it too. He gave himself the nickname “The Chosen One” while in college, and the Browns made him the highest-paid tight end in league history after taking him with the sixth pick of the 2004 Draft.

Although injuries meant he never quite lived up to the advance billing, the Tampa Bay Buccaneers, the New England Patriots and the New York Jets all gave him opportunities before a failed drug test in 2013 finally ended his career. Throughout those years in the spotlight, he had already evinced predilections that troubled those in his orbit.

"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," wrote Robert Klemko in a forensic Sports Illustrated piece that was a throwback to that magazine's glory days. "When pornography became widely available on mobile phones, he often watched it on his smartphone during meetings, the two former teammates said (nowadays, such sites would typically be blocked by the building WiFi). Later on in his career, Winslow acquired a life-sized silicone mold of a woman's torso – complete with vagina and anus – to bring with him on road trips . . ."

Even in the demi-monde of professional athletes, traditionally the most promiscuous and licentious of constituencies, Winslow’s obsessive, compulsive sexual behaviour marked him out from the crowd. Right from the start. In his first season, the Browns arranged for a photo shoot of him and his celebrated father. When he couldn’t be located for the publicity shot, a club employee discovered him in the car park, sitting in the back of his truck, masturbating. Fourteen years after that incident, he was found shirtless entering the trailer park home of an 86-year-old woman who police believed he would have raped only for a neighbour calling 911.

Depraved behaviour

Before the trial in which the father of two never testified, there was speculation his lawyers might argue their client’s depraved behaviour was somehow caused by CTE (chronic traumatic encephalopathy) in his brain from hits received on the football field. The problem with that defence is CTE can only be diagnosed posthumously and he is the lone former NFL player who has been accused of repeatedly sexually menacing elderly, vulnerable women. Not to mention Winslow has a track record of violent conduct from way back.

In high school, he assaulted a fellow student and had to settle a $3m lawsuit out of court. And one of the outstanding rape charges against him dates back to when he was 19 and is alleged to have attacked an unconscious 17-year-old girl.

His is a reckoning that has been a long time coming.