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

Former NFL player Kellen Winslow II talks to his defense attorney Marc Carlos.
Former NFL player Kellen Winslow II, left, talks to his defense attorney, Marc Carlos during a February 2020 hearing in the San Diego Superior Court in Vista.
(Howard Lipin / San Diego Union-Tribune)

Former NFL player Kellen Winslow II agreed Friday to a change in his rape-case plea deal so he could secure 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 12 to 18 years in prison following his convictions for raping a homeless woman and charges linked to misconduct with other women.

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

To achieve this, Winslow’s 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.

Superior Court Judge Blaine Bowman approved the change Friday 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 he would be able to “get an actual jury of my peers, people of color that would look like me?” if he were to go to trial.

Bowman told Winslow he would have to withdraw his guilty plea to go to trial and allowed Winslow to discuss it 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 whom he had convinced to join him for coffee, as well as two misdemeanor sexual misconduct charges involving two strangers. But the panel was hung on other charges, including two counts of raping two other women.

As his retrial was about to start five months later — 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.