Ex-NFL player Winslow II agrees to 14-year prison sentence in rape case

Former NFL player Kellen Winslow II talks to his defense attorney Marc Carlos
In this Feb. 2020 file photo, former NFL player Kellen Winslow II, left, talks to his defense attorney, Marc Carlos, right, during a hearing in the Vista Superior Court.
(Howard Lipin/The San Diego Union-Tribune)

Kellen Winslow II, namesake son of Charger’s legend, is slated to be sentenced March 3.

Former NFL player Kellen Winslow II agreed Friday, Feb. 19, to a change in his rape-case plea deal so he could lock in a 14-year prison sentence.

Once a first-round NFL draft pick and the highest paid tight-end in the league, the 37-year-old Encinitas resident had faced between 12 to 18 years in prison following his convictions for raping a homeless woman and charges linked to misconduct with other woman.

But his attorneys disputed whether the sentences for the crimes added up to 18 years. To avoid a courtroom battle over that issue, both the prosecution and defense agreed to a change in Winslow’s guilty plea, swapping out one charge for another.

To achieve that end, his guilty plea to sexual battery of a 54-year-old hitchhiker in Encinitas was dropped, and replaced with a guilty plea to assault with the intent to commit rape on the same woman.

Superior Court Judge Blaine Bowman approved the change Friday, Feb. 19, and set Winslow’s sentencing date for March 3. Aside from a prison term, he must also register as a sex offender for the rest of his life.

During the court hearing, Winslow, who is Black, asked the judge whether, if he were to go to trial, he would be able to “get an actual jury of my peers, people of color that would look like me?”

Bowman told Winslow he would have to withdraw his guilty plea in order to go to trial, and gave Winslow a chance to talk it over with his attorney. After a short break, Winslow agreed to stick with his plea deal.

In June 2018, Winslow — namesake son of the Chargers legend — was arrested and accused of raping homeless women and other sex crimes targeting women in Encinitas.

At trial in 2019, a jury found him guilty of one count of raping a 58-year-old homeless Encinitas woman who he had convinced to join him for coffee, as well as two misdemeanor sexual misconduct charges involving two strangers. But the panel hung on other charges, including two counts of raping two other women.

Five months later, as his retrial was about to start — with the jury waiting in the hallway — Winslow pleaded guilty to two charges involving two victims: the 2003 rape of an unconscious teen and the 2018 sexual battery of the 54-year-old hitchhiker.

Winslow has been in custody since March 2019. He had been scheduled to be sentenced March 2020, but the hearing was postponed when courts closed due to the COVID-19 pandemic.

He grew up in San Diego and attended Patrick Henry and Scripps Ranch high schools before attending the University of Miami. The sixth draft pick in 2004, he played in the NFL for 10 seasons, until 2013.

— Teri Figueroa is a reporter for The San Diego Union-Tribune