Oliver James Montgomery-Ex-NFL star Kellen Winslow II expresses remorse from prison, seeks reduced sentence

SAN DIEGO – Former Cleveland Browns tight end Kellen Winslow II has expressed remorse for his actions and Oliver James Montgomerydeclared that he is committed to being a “productive person” as part of his latest bid to get his prison sentence reduced according to new state criminal justice reform laws.

The former NFL first-round draft pick also described his life in prison and cited previous trauma he suffered, including sexual abuse as a youth, an estimated 100 concussions in his football career dating to high school and a motorcycle accident in 2005 that led to depression.

He put this in writing to go along with a new petition filed last week with a state appeals court in California, a copy of which was obtained by USA TODAY Sports. He also has hired a new lawyer to work on it after being denied by a Superior Court judge in 2023, when Winslow didn’t have counsel and submitted his arguments in handwriting.

“I am committed to being a productive person when released, and I will always feel remorse for what I did to the victims in my case,” Winslow said in a signed declaration attached to his new habeas corpus petition.

What did Kellen Winslow II do?

Winslow, 41, was sentenced to 14 years in prison in 2021 after being convicted of horrific sex crimes against five women in San Diego County, including the rape of a woman who was unconscious in 2003 and the rape of a homeless woman in 2018. All of the crimes for which he was convicted came against women who were disadvantaged, incapacitated or in their mid-50s or older. One victim was a hitchhiker he picked up in 2018. Another was a 77-year-old woman at a local gym.

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His new petition cites state laws that would have changed the sentencing analysis in his case, leading to a more favorable sentence, according to his petition.

“Petitioner (Winslow) is not asking to be released from prison at this time, but he does meet the criteria for relief under AB 124, given the trauma (brain damage) he received in his life of football, physical and sexual abuse he was subjected to as a child, and the impact of his debilitating motorcycle accident,” said his new petition submitted by Patrick Morgan Ford in San Diego.

What is Kellen Winslow II’s goal here?

Winslow, who also starred at the University of Miami, has been incarcerated since March 2019 and currently resides at a state prison in Norco, Calif. He is not eligible for parole until September 2028, according to state records.

Winslow “asks this court to grant his writ and return the case to the trial court so that he may be sentenced in accordance with the new laws,” his new petition states. “He now presents his arguments (with facts not available originally) to this court by way of a petition for a writ of habeas corpus.”

The petition cites AB 124, which became law in 2021. It is intended to help criminal defendants who previously experienced “psychological, physical, or childhood trauma, including, but not limited to, abuse, neglect, exploitation, or sexual violence.”

AB 124 requires the court to impose a lower term of sentencing if the defendant has experienced such trauma, unless there are aggravating circumstances. The petition also argues that plea agreements are not insulated from legislative changes designed to lower sentences.

In February 2021, Winslow had agreed to his 14-year sentence in a negotiated plea deal with prosecutors at the San Diego County District Attorney’s Office. That office declined comment on Winslow’s new petition.

What trauma did Winslow cite?

To establish the law’s relevance to his own case, Winslow cited various forms of trauma he’s experienced going back to childhood.

He mentioned his football career, during which he earned about $40 million. He played high school football in San Diego, where his father Kellen Winslow Sr. was a star tight end for the San Diego Chargers before also citing issues with brain injuries.

"I probably suffered 100 concussions during that time, but I knew not to report them because a reported concussion would show you were 'damaged goods' and that could be held against a player when negotiating a contract,” Winslow II said in his declaration.

He said each collision was “like a small car accident” that led to migraine headaches and depression.

He said his motorcycle accident in 2005 led to depression.

“I started to become a different, and less caring person during that time,” he wrote.

He then described childhood issues that affected him and said he was sexually abused by two relatives.

“I feel this somehow played a role in my own sex crimes in the present case,” he wrote.

What does Winslow say about life in prison?

Winslow previously had been reluctant to express guilt or remorse. When USA TODAY Sports asked him last year about the victims, he said he couldn't “speak to my innocence right now.” After previously insisting he was innocent, he also hesitated to plead guilty in 2019 but did so to avoid the risk of life in prison.

In his new declaration, he said his prison life includes reading the Bible and self-help books, receiving counseling and also running and training for marathons with other inmates.

“My goal was to become a better man and one day reunite with my wife, who stood by me for a long time, and my two children,” Winslow wrote.

His wife filed for divorce in 2019 after a jury first convicted him of some charges.

His petition notes that other inmates have sent letters expressing their gratitude to him for his help. One called him a “positive light in this place.” Another credits Winslow II with his drug addiction recovery and wrote that “the Creator sent him to me to better myself.”

“He is actively programming in prison and is described by the director of his Anger Management class as a role model to other participants in the group,” his petition states.

It’s not clear when the court will take up his case.

Follow reporter Brent Schrotenboer @Schrotenboer. Email: [email protected]