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Ex-NFL star Kellen Winslow II agrees to 14 years behind bars for sex crimes

  | USA TODAY

SAN DIEGO – Former NFL player Kellen Winslow II has agreed to a new plea deal that will punish him with 14 years behind bars for raping two women, assaulting another and committing misdemeanor sex crimes against two others, according to an agreement submitted Friday in San Diego Superior Court.

The new plea agreement replaces a prior plea agreement in his case from November 2019, when he pleaded guilty to rape and sexual battery charges to avoid the possibility of spending the rest of his life in prison. The previous deal stipulated a sentencing range of 12 to 18 years behind bars, to be determined by the judge after a sentencing hearing. 

Winslow, 37, appeared remotely in a court hearing from his jail in San Diego County.

“I would like to agree to 14 years,” Winslow told Judge Blaine Bowman.

The new deal also includes another significant change: a new guilty plea by Winslow for assaulting a hitchhiker with the intent to commit rape in March 2018 – a woman in her mid-50s who was known in the case as Jane Doe 1. That new guilty plea replaces a guilty plea he made in November 2019 for sexual battery against the same woman.

Winslow still had a question for Bowman before the hearing adjourned.

“I just wanted to know if I was to go to trial would I get an actual jury of my peers that (are) people of color that would look like me?” asked Winslow, whose attorneys previously raised this issue in 2019. “Would I get jury trial like that?”

Bowman responded that this was not at issue in the hearing. He then called for a recess so that Winslow could talk to his attorney about whether he wanted to proceed with the new deal. After a short break, Winslow agreed to it.

Final judgment will come at Winslow’s sentencing hearing March 3.

In the meantime, the deal raises the issue of leniency for a man who committed sex crimes against five women, including raping a homeless woman, raping an unconscious woman and assaulting the hitchhiker in a parking lot behind a shopping center.  

Is 14 years enough for that?

San Diego County Deputy District Attorney Dan Owens noted that the jury in Winslow’s first trial in the spring of 2019 wasn’t able to reach a unanimous verdict on all the charges he faced. Winslow could have gotten an even lighter sentence if he went to a trial again on those unresolved charges.

Owens also noted that the new guilty plea involving assault with the intent to commit rape is for a violent sex offense, unlike sexual battery. This carries more serious consequences for Winslow as a result. 

“Ultimately, we think this was the most appropriate sentence for Mr. Winslow’s conduct,  taking those other things into account,” Owens told USA TODAY Friday. 

It was a tradeoff. Under the previous plea deal, the San Diego County District Attorney’s Office sought the maximum term of 18 years, saying Winslow “committed these despicable crimes despite being afforded every advantage in life.” Owens previously noted “he selected victims who came from much less fortunate backgrounds.”

Winslow almost was sentenced last year under the previous deal. But then came the COVID-19 pandemic, which delayed Winslow’s sentencing shortly before it was scheduled last March. Winslow’s attorneys also made the case that the previous plea deal of 12 to 18 years went beyond what the law allows. They argued 12 years should be the limit under the law, according to court records they filed last year.

This then raised the possibility of the court invalidating the 2019 plea agreement, forcing Winslow to go to a new trial and face the possibility of life behind bars all over again.

The new agreement helps each side avoid risk with a compromise. The prosecutor avoids the risk of Winslow getting a much shorter sentence and Winslow avoids those risks associated with another trial.

“After a lot of back of forth, we have agreed to withdraw the guilty pleas and enter into a new plea agreement,” Winslow’s attorney Marc Carlos said.

All of Winslow’s crimes came in San Diego County, where he was born and where his namesake father became a Hall of Fame tight end for the San Diego Chargers in the 1980s.  

►At his first trial in June 2019, a jury found him guilty of raping a homeless woman in May 2018, exposing himself to a woman in his neighborhood that same month and making a lewd gesture with his genitals toward a woman at a local gym in February 2019. Each of the women were in their late 50s or older.

►In November 2019, he admitted guilt to raping an acquaintance while she was unconscious at a party in 2003, when she was 17 and he was 19.

►In his new plea agreement Friday, he pleaded guilty to assaulting the hitchhiker with the intent to commit rape.

Winslow, who earned about $40 million during his NFL career, has been in jail since March 2019, which will count toward his punishment.

At the time of his first trial in spring 2019, Winslow been married with two children: a son, now age 9, and a daughter, age 7. That changed later that year when his wife filed for divorce, just months after the jury in that trial convicted him on some of the charges.

That same jury in June 2019 could not reach a unanimous verdict on other charges against him, leading to a retrial by a new jury on those counts scheduled for November 2019.

If the new jury had convicted on those remaining counts, he faced the possibility of spending the rest of his life in prison. But Winslow instead opted to avoid that risk by making a plea agreement in November 2019 in which he pleaded guilty to two additional counts: felony sexual battery of the hitchhiker and the rape of the unconscious woman.

Winslow’s attorneys also previously argued that Winslow suffered from brain injuries from football and a motorcycle accident in 2005, which they suggested led to changes in his behavior. They said he has frontal lobe damage and symptoms associated with chronic traumatic encephalopathy (CTE), which is linked to football head trauma.

They estimated he sustained more than 1,000 blows to the head during his career with the University of Miami, Cleveland Browns and other teams. He last played in the NFL in 2013.

Follow reporter Brent Schrotenboer @Schrotenboer. E-mail: [email protected]

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