The sentencing hearing for former NFL star Kellen Winslow II was finally at hand. As the proceedings began on March 3, 2021, gone were the days of a packed courtroom overflowing with media, family members, and the interested public. The hearing now was conducted via video due to COVID-19 restrictions. Yet San Diego Superior Court Judge Blaine Bowman spared no words before pronouncing judgment. Quickly dismissing the defense’s contention Winslow’s spree of sexual crimes was the result of CTE and traumatic brain injuries from years of sustained football blows and a motorcycle accident, Judge Bowman said bluntly, “That leaves us with someone who can only be described in two words – and that is a sexual predator. That is what Kellen Winslow II is.” He went on to describe his crimes as brazen and stated he preyed on vulnerable victims. “The vulnerability of the victims was no accident,” said Judge Bowman before declaring Winslow thought these women would not report nor be deemed credible.

Though Judge Bowman’s words may have been surprising to Kellen Winslow II, the sentence was not as a stipulated agreement had been reached just weeks before delineating a sentence of 14 years for the multiple rapes and sex crimes involving five different women. Previously Winslow had been looking at a range between 12-18 years with Judge Bowman making the final decision. Winslow must also register as a sex offender.

 A Long Fall For the Former NFL Star

It was a long fall for Kellen Boswell Winslow II, the former NFL star who at one time had it all: fame, fortune, and a celebrated name. Born into football royalty, the namesake son of legendary football Hall of Famer Kellen Winslow Sr., Kellen Jr. too achieved football stardom. As he set records, received prestigious honors, and over 40 million during his decade in the NFL, he seemed unstoppable. With his extreme wealth, stunning wife, and beautiful young children, Kellen Winslow II’s life appeared perfect. But was there another side to him? According to five accusers there was, and if they were to be believed, it was a dark, frightening side.

As 35-year-old Kellen Winslow II’s rape trial began in a San Diego courtroom in May 2019, all five women took the witness stand, forever known as Jane Does 1 through 5, in the 12-count consolidated criminal case against him. The searing charges held a potential life sentence. Kidnapping and rape of a 54-year-old hitchhiker, rape of a 59-year-old homeless woman he had befriended, rape of an unconscious 17-year-old at a house party (when Kellen Jr. was a 19-year-old college student), indecent exposure to a 57-year-old neighbor gardening in her front yard, and lewd acts before a 77-year-old woman at a gym. Ugly charges to be sure, but were they true? And how had it come to this?

 The Trial: Jane Does 1 through 5 Take the Witness Stand

The trial incited a media frenzy, with reporters sent from every sector, both locally and nationally, and with Court TV and the Law & Crime Trial Network covering the trial gavel-to gavel. The jury was tasked with deciding Kellen Winslow II’s fate. Was he a depraved, sexual predator, preying on the most vulnerable of women as the prosecution contended? Or was consent freely given and claims cruelly fabricated by opportunistic women seeking financial gain from a wealthy superstar as the defense maintained? Were the elderly women simply mistaken about identity and to what had truly transpired? And did overzealous law enforcement and nonstop media coverage contribute in some way to false claims?

Jane Doe No. 1, a 54-year-old hitchhiker testified to the Spring day in 2018 when Winslow picked her up on a street in Encinitas for a lift to the nearby coast. Instead, she said he took her behind a shopping center where he raped her and threatened to kill her if she told anyone. Jane Doe No. 1 was no match for Winslow’s attorney, Marc Carlos who destroyed her on cross-examination showing she lied to the jury about her drinking arrests and that she changed her story on key facts. It was a rough start for the prosecution, which only got worse when Jane Doe No. 1’s daughter made a surprise appearance. After her testimony she promptly went on Court TV to reveal she had set up a GoFundMe Me page for her “mentally ill mother,” asking for $50,000 for her recovery. It was manna from heaven for the defense: A mentally ill accuser and a money grab in one quick swoop.

Jane Doe No. 2, a 59-year-old homeless woman testified to the time Winslow gave her a ride to a homeless shelter and then for months after checked up on her wellbeing. On Mother’s Day of 2018, she agreed to have coffee with him. Instead, he drove on and on into the night, until stopping in a secluded location where he raped her repeatedly. She testified she thought she was going to die.

Jane Doe No. 3, a 57-year-old Vietnamese woman, testified with the aid of an interpreter, of how Winslow followed her into her yard while she was gardening and exposed himself to her.

Jane Doe No. 4 came forward after hearing of Winslow’s arrest, stating he had raped her too when she was a 17-year-old high school girl. Winslow was 19 at the time. Upon her first meeting with Winslow, she had consensual sex with him, but at a party weeks later, she said he raped her while she was blacked out. Once again, attorney Carlos subjected Jane Doe No. 4 to intense cross-examination. Hadn’t she told a completely different story to the supervisor of the sex crimes unit?

Jane Doe No. 5, a 77-year-old woman testified about Winslow committing a lewd act before her while she was working out at a Carlsbad gym and on a second occasion sat next to her in the club jacuzzi. Beneath the swirling bubbles, she believed he was masturbating.

The Jury Returns a Verdict

After weeks of emotional testimony, dissection of all the disturbing and shocking facts, and vigorous legal combat, the case went to the jury. On June 10, 2019, the jury returned with a partial verdict. In a strong voice the court clerk began reading the long formalities. Winslow looked nervous, looked down, murmured words to himself, and reached for a glass of water. She finally got to the verdict. Count No. 4 for rape of Jane Doe No. 2: Guilty. As the words rang out, Kellen looked confused. He turned to attorney Brian Watkins, who whispered, “It’s okay.” Count No. 6 for indecent exposure to Jane Doe No. 3: Guilty. After this announcement, Kellen shook his head and looked stunned, completely dazed by the words he was hearing. His dad sitting in the rows behind him, closed his eyes. The counts continued. Count No. 9 lewd conduct at the gym for Jane Doe No. 5: Guilty. Would all four counts be guilty? No. Finally, there was a reprieve. Count No. 10 lewd conduct in the gym jacuzzi for Jane Doe No. 5: Not Guilty.

The jury remained deadlocked on the remaining eight counts, despite an additional day to deliberate. The jury’s finding was read in court on June 11, 2019:

Counts 1-3: Jane Doe No. 1 Kidnapping, Rape and Oral Copulation: 5 to 7, with 7 favoring guilt

Count 5: Jane Doe No. 2 Sodomy: 10 to 2, with 10 favoring guilt

Count 7: Jane Doe No. 4 Rape: 10 to 2, with 10 favoring guilt

Count 8: Jane Doe No 4 Rape of an Unconscious Person: 8 to 4, with 8 favoring guilt

Count 11: Jane Doe No. 5 Willful Cruelty to an Elder: 10 to 2, with 10 favoring guilt

Count 12: Jane Doe No. 5 Battery Against an Elder: 10 to 2, with 10 favoring guilt

The San Diego District Attorney’s office decided to retry Winslow on the remaining eight counts. The stakes were high: just one more rape conviction would send Winslow to prison for life.

A Bombshell Announcement at Winslow’s Retrial

On November 4, 2019, Winslow’s retrial began. Once again, the courtroom overflowed with media. Court TV and the Crime & Trial Law Network were set for gavel-to-gavel coverage. But then came a bombshell announcement. With the jury waiting in the hallway, Judge Bowman declared Kellen Winslow II would plead guilty! Everyone was stunned! Had everyone heard correctly? A guilty plea to rape of an unconscious person for Jane Doe No. 4 and sexually battery for Jane Doe No. 1. Remaining counts: dismissed. No longer looking at a potential life sentence, the agreement specified a sentence between 12 to 18 years. Judge Bowman would determine the final sentence.

It was an incredible deal for Winslow, yet he did not want to take it. Back and forth it went with Judge Bowman repeatedly telling Winslow he did not have to take the deal and his jury trial could proceed immediately. It was a torturous decision anyone could see with Winslow requesting additional time and turning to look at his father for guidance. At last, he entered his plea. It was over. Sentencing was set for March 20, 2020. However, the COVID-19 pandemic shut down the court system that very week and it was anybody’s guess when he would be sentenced.

The Defense Raises CTE and Traumatic Brain Injury

In anticipation of the sentencing, the prosecution filed their “Statement in Aggravation” requesting the full 18 years, citing the level of violence, depravity, the vulnerability of the victims, and stating Kellen Winslow II was a serious danger to society.  The defense countered with a request of 13 years. In their “Statement in Mitigation” they argued Winslow needed mental health treatment as he suffered from traumatic brain injury (TBI) and CTE (Chronic Traumatic Encephalopathy) resulting from a motorcycle accident and his 15 years of football playing (10 in the NFL).  He sustained over 1,000 blows to his head they wrote.

According to Boston University’s Chronic Encephalopathy Center, CTE is a degenerative disease of the brain found in people with a history of repetitive brain trauma, such as those received by military personnel and athletes, including football players, boxers, and hockey players. The repeated brain trauma or head impacts trigger progressive degeneration of the brain tissue. Although CTE can only be definitely diagnosed post-mortem, the defense’s medical experts stated Winslow exhibited classic signs of CTE.

Dr. Jay Faber performed brain scans on Winslow and found damage to his frontal lobes. Winslow’s attorneys referenced a 2008 study from the Libyan Journal of Medicine stating injury to the prefrontal convexity may result in hyposexuality causing loss of impulse control and inappropriate sexual behavior. Also cited was a 2007 study from the Journal of Neurology, Neurosurgery, stating injury to the frontal lobes can cause disinhibited sexual behavior. Would these factors persuade Judge Bowman for a lesser term? The defense believed it should.

A Remarkable Deal and Day of Sentencing

Almost an entire year went by, and as it turned out neither side had to argue their positions at all. Instead, a new agreement was reached. Winslow’s guilty plea to sexual battery of Jane Doe No. 1 was dropped and replaced with a lesser plea to assault with the intent to commit rape. With this change, a 14-year prison term was locked in. On February 19, 2021, the amended change of plea was entered into the court record, with final sentencing set for March 3, 2021. From once facing a potential life sentence, Winslow had achieved a remarkable deal.

Although the sentence was known to all, on March 3, 2021, Winslow’s victims read their Victim Impact Statements to Judge Bowman. Deputy District Attorney Dan Owens read Jane Doe No. 1’s statement. The former 54-year-old hitchhiker wrote, “I was so scared when he raped me…. He scared me so bad, knowing now that he was my neighbor, and I couldn’t believe that an NFL football player would take advantage of me.” She said she was scared to go outside not knowing who it was. She hopes he serves the 14 years and gets the help he needs.

Jane Doe No. 2, the former 58-old homeless woman, broke down at times as she said her life has been taken and that rape affects life every day, every night. She said she doesn’t ever feel safe, inside or outside. “I don’t think you know how truly dangerous this man is” she said in a shaky voice.

Jane Doe No. 4, the former 17-year-old high school girl, cried, as she did many times on the witness stand, as she read her statement.  She said the rape has not only affected her emotionally and physically but has affected her family as well. “Mr. Winslow has hurt me and damaged me for so many years.” She closed by saying after she came down from the stand, she felt she had a voice and felt empowered. “Every victim should have a voice” she finished. Her husband spoke and said effects of rape are lifelong and not just for the victims. He cannot quantify the damage done to his family.

Jane Doe No. 5, the former 77-year-old woman from the gym, said she “can’t describe the emotional impact.” She was the perfect victim and despite receiving therapy, “I’m not sure if I will ever let up.” She said Winslow is a sexual predator and must be stopped. Jane Doe No. 3, the 57-year-old neighbor who was gardening in her front yard when Winslow exposed himself to her chose not to give a statement.

Deputy District Attorney Dan Owens spoke next. His remarks were brief this time, unlike his long passionate closing argument to the jury. He thanked the victims and talked about the genuine impact the crimes have had on them. He told Judge Bowman the impact had “significant consequences,” even the lewd act before Jane Doe No. 5. He said he believed the 14 years was appropriate given the jury’s findings, the evidence, and Winslow’s admissions. He hoped the sentence would give a measure of justice.

The defense team was represented by attorney Marc Carlos, who had been a fierce advocate during the trial. He emphasized Winslow took responsibility for his actions by entering a guilty plea even when he had appealable issues from the first trial. He said Winslow was 37 years old, a family man, and all he wants to do is get back to his two children, so “they know who he is.” He talked about a “deep, deep spiral” of depression and anxiety Winslow experienced after severe injuries from his motorcycle accident and how he self-medicated with pain medications, Spice, and “anything he could get ahold of.”

He then turned to the “elephant in the room,” the CTE. He went through all the head injuries, referencing the 1,000 blows, and then said CTE “builds, and builds and builds.” He said the reason it was important was the frontal lobes control decision making and impulse control. He proclaimed Jane Doe #4 consented and then there was a break of 17 year before anything else happened. It was the CTE building. He said Dr. Hopper believed Winslow can be treated and he will receive the medical treatment he needs in prison.

Judge Bowman then gave Kellen Winslow II the chance to speak. Winslow said he had been advised by his attorneys not to speak right now, but in the future, plans to tell his story.

Judge Bowman’s Final Words

It was time to hear from Judge Bowman. He praised the victims’ courage, before saying Winslow carefully selected his victims, and their vulnerability was no accident. Judge Bowman characterized Winslow’s actions as brazen. He dismissed the defense’s claims of CTE, stating CTE was not present in 2003 when he raped Jane Doe No. 4. He then said, “That leaves us with someone who can only be described in two words – and that is a sexual predator. That is what Kellen Winslow II is.”  He discussed the “tortured change of plea” to avoid the life sentence and said there was no question in his mind Winslow was guilty of these crimes. He affirmed the 14 years and the sex offender registration. “Good luck to you Mr. Winslow,” he closed. And then it was over.

Aleida K. Wahn, Esq.’s Book Takes You Inside the Trial

I attended the entire 2019 trial of Kellen Winslow II.  As the trial delved into shocking facts, complicated legal issues, and unexpected twists and turns, I was there for every minute and provided my insight and expertise on Court TV and the Law & Crime Trial Network. Following the trial, I wrote an Amazon eBook on the case, going behind the headlines to share the extraordinary details of what happened inside the courtroom. Judging Winslow Jr.: From NFL Star to Serial Rapist? Inside the Shocking Rape Trial of Kellen Boswell Winslow II is available on Amazon at:

About Aleida K. Wahn, Esq.

I am an attorney, award-winning true crime writer, and legal analyst of criminal cases. I cover criminal trials and write stories and books about compelling, gripping, and unforgettable cases that impact our world. I take you into the courtroom in high-profile murder trials, rape cases, crimes of passion, cases involving mental illness, deviant behavior, and more. I have a deep passion for true crime, criminal law, and all aspects of the criminal justice system. I have appeared as an expert on true crime shows, including “48 Hours,” “Snapped,” and “The Dead Files,” and provided legal analysis on high-profile criminal trials on Court TV, the Law & Crime Trial Network, Fox 5 News, ABC 10 News, and KUSI News. I also create and host shows with the Del Mar Television Producers Group, addressing criminal justice and social issues in recent criminal trials.

I provided my insight and legal analysis on Court TV and the Law & Crime Trial Network of the high-profile trial of former NFL star Kellen Winslow Jr. It was a trial that captured the nation as the heralded ex-football star with fame, fortune, and a famous name stood accused of multiple rapes and other sex crimes involving five women. As the trial delved into shocking facts, complicated legal issues, and unexpected twists and turns, I was there for every minute. After the trial, I wrote a book on the case, going behind the headlines to share the extraordinary details of what happened inside the courtroom. Judging Winslow Jr.: From NFL Star to Serial Rapist? Inside the Shocking Rape Trial of Kellen Boswell Winslow II is now available on Amazon.

I am passionate about telling true crime stories, as these penetrating stories have the power to move us all, while highlighting societal issues which need to be addressed. I have personally seen the human devastation which is present in each trial and believe there is a lesson to be learned in every single case. It is through awareness and examining critical issues society can effect change and even make new laws. To learn more, please visit:

Read about the gripping and unforgettable trials that I have covered in my latest books: