How Kellen Winslow Jr went from NFL star to accused serial rapist
By JOSH PETER AND A.J. PEREZ | USA Today | Published: July 31, 2018
VISTA, Calif. (Tribune News Service) — The witness known as Jane Doe 2 moved closer to the microphone when she was asked to speak up.
She appeared to be avoiding eye contact with the defendant, Kellen Winslow II, the retired NFL player who sat across the courtroom. One of his attorneys asked the 58-year-old homeless woman about having testified Winslow choked her during sexual intercourse.
"It wasn't intercourse," she responded. "It was rape. You need to use your words correctly, sir."
It was the morning of July 12, and tension was rising inside the North County Division of the San Diego Superior Court during a pretrial hearing in a case that's as disturbing as it is confounding.
Winslow, 35, is the son of an NFL Hall of Famer; the sixth overall pick in the 2004 NFL draft who made almost $40 million in salary as a tight end during his 10-year pro career; and the husband of his high school sweetheart and father of their two young children.
In question: If and how he also could be a rapist.
He is facing eight felony counts, which include kidnapping and raping two homeless women in their 50s and raping an unconscious, 17-year-old female in 2003 when Winslow was 19. USA TODAY Sports does not identify alleged victims of sexual assault.
Winslow, whose next court appearance is scheduled for Aug. 25, has pleaded not guilty to all charges, and his attorneys have left open the possibility of arguing Winslow paid for consensual sex with the homeless women and had consensual sex with the then-17-year-old.
Both of the homeless women testified that they rejected Winslow's offer of $50 for sex. When one of Winslow's attorneys asked Jane Doe 2 why she waited until shortly before the pretrial hearing before disclosing the money-for-sex offer, she said she forgot.
"I mean, what does that have to do with rape, sir?" she said, her voice rising. "I'm the victim."
Earlier in the day, under questioning by deputy district attorney Dan Owens, Jane Doe 2 said she and Winslow met about 7 1/2 months ago and saw each other periodically thereafter. The first time, the woman said, she was walking toward a homeless shelter in nearby Encinitas, where Winslow lives.
He pulled over in his black Hummer, offered her a ride and she accepted, Jane Doe 2 testified.
"Very friendly, very nice," she said of her impressions of Winslow, but she also noted she was offended when he later offered her money for sex and regained her trust when over time he repeatedly asked how she was doing and if she needed food. "He seemed like a friendly person."
But, the woman testified, she encountered a much different Winslow on the evening of May 13.
After celebrating Mother's Day with a friend, Jane Doe 2 testified, she was at a transit station in Encinitas between 8 p.m. and 9 p.m. when Winslow pulled up in his Hummer. He offered to take her for coffee and she accepted, the woman said.
"At that time," she said, "I felt very safe with him."
But just minutes into the ride, the woman testified, she grew uneasy.
"I just kept asking him questions and it was like he didn't want to answer," she said.
Winslow made a quick U-turn, pulled the Hummer over to the shoulder of the road and, the woman said, she feared for her life.
"I said, 'No, please don't do this,' and I said it about four times," the woman testified, adding that Winslow responded by saying something along the lines of, "It's a done deal."
Moments later, Jane Doe 2 said, Winslow pulled her out of the car by her wrists and raped her. When she screamed with pain, Jane Doe 2 said, Winslow choked her and said, "If you scream, I'll kill you."
That rage -- if not the act of rape -- conjures memories of Winslow on and off the football field. Damon Shaffer, who coached Winslow and coached against him when Winslow was in high school, said "cheap-shot artist" was an accurate description. And while playing for the University of Miami, Winslow launched into an infamous post-game tirade.
"It's war," he fumed in the locker room after Miami's 10-6 loss to Tennessee on Nov. 8, 2003. "They're out there to kill you, so I'm out there to kill them. ... I'm a (expletive) soldier."
That image contrasts with the good-natured Winslow that Skip McDowell, owner at Nytro Multisport in Encinitas, described in a recent interview with USA TODAY Sports. Winslow became an avid cyclist after his NFL career, and McDowell said Winslow stopped by the store as often as every other week.
"Unassuming, quiet, didn't talk too much about football," McDowell said. "I didn't see any demons in his head. Honestly, all of us at the shop were in shock after the allegations."
Jonathan Deguzman, who attended Scripps Ranch High School in San Diego with Winslow, said he has seen rageful and peaceful sides of the former football star.
In high school, Deguzman said, Winslow was known in part for his temper. As a senior in 2001, Winslow was sued for $3 million by a classmate who said Winslow kicked and punched him in the face, resulting in a broken jaw, an eye injury and head injuries. (The matter was settled out of court.)
But Deguzman, a competitive cyclist, said he was struck by Winslow's easygoing nature in 2014 when they saw each other at a bike race and got reacquainted. Deguzman said they rode together a few times and stayed in touch for about a year. He recalled ordering Winslow a bike and that when the delivery was delayed, there was no sign of Winslow's old temper.
He was very patient, Deguzman said, adding that he had conflicting thoughts after hearing Winslow had been charged with rape.
"Part of me can't believe it," Deguzman said. "And part of me can."
As the son of a Hall of Fame tight end who starred for the San Diego Chargers from 1979 to 1987, it would seem Winslow had an envious childhood. But he was born into a world of turmoil.
In 1984, a San Diego County court issued mutual restraining orders against his parents, Kellen Winslow Sr. and Katrina Winslow.
Kellen Winslow Sr. had filed for divorce in 1983, and records in the case file show Katrina Winslow accused him of assault. The alleged incident took place May 28, 1983, when Kellen Winslow Sr. arrived at the family residence without notice and told Katrina Winslow he intended to move the furniture out and into his new residence, according to court records.
"It is true that I became very upset when he allowed the movers to begin moving the furniture," Katrina Winslow stated in court records. "I did throw an iron and a brick. However, his television set was never ... broken. It must be kept in mind that the Petitioner undertook to make this move in a residence in which I was living at a time when I was 7 1/2 months pregnant. Furthermore, the Petitioner had pushed me to the floor on several occasions and had held me there to stop me from preventing the movers from taking the furniture. I ended up with several bruises about my body as a result of the Petitioner's physical assault."
Kellen Winslow Sr. leveled allegations against Katrina Winslow, who in court records is identified as the Respondent.
"On or about February 15, 1984, while the Petitioner was exercising his custodial rights with his son, Respondent came to the Petitioner's then home in Spring Valley, California and attempted forcefully to take the child from Petitioner," court records state. "It was necessary to call the Sheriff's office. Respondent was ordered by the Deputy Sheriff to leave Petitioner's home and to cease disturbing the Petitioner and the baby."
At that time, according to court records, Kellen Winslow Sr. periodically traveled to Kansas City to be with his girlfriend, Dawnn Wimes, who was pregnant at the same time Katrina Winslow was.
Kellen Boswell Winslow II was born in San Diego July 21, 1983. His half-brother, Justin, was born April 8, 1983.
At age 5, Kellen Winslow II moved with his mother to Maryland. But by the time he entered high school, he had moved back to San Diego with his father.
He excelled on the football field and basketball court, and in 2001 he accepted a scholarship to Miami. Other than the fight that year that led to a $3 million lawsuit against him, Winslow was in no serious trouble. But now, the San Diego County District Attorney's office says, in 2003 he raped an unconscious, 17-year-old female when Winslow was 19.
The alleged rape took place in the Scripps Ranch area where Winslow lived with his father while attending high school and was home from Miami, according to court records.
Winslow has pleaded not guilty to those charges and the other criminal counts -- kidnapping, forced oral copulation, sodomy by use of force, indecent exposure and unlawfully entering a home occupied by a 71-year-old woman and a home occupied by an 86-year-old woman.
Winslow, who is fighting to avoid life in prison, faced another court battle in 2008: for his reputation.
It was a decade ago that Winslow filed a civil lawsuit against an Ohio man for extortion, claiming the individual and other unidentified defendants threatened to ruin his football career and public image with "salacious lies and innuendo." The Ohio man, Cleveland Scruggs, and other unnamed defendants demanded $5 million from Winslow and he refused to pay, according to the lawsuit.
At the time of the lawsuit, Winslow, picked by the Cleveland Browns sixth overall in the 2004 draft, had completed his fifth season in the NFL. He expected to suffer more than $25 million in damages and much of the public would view him as "a crazed sports figure," according to the lawsuit.
Scruggs, reached by phone by USA TODAY Sports, declined to comment other than saying the matter stemmed from a "skirmish." The lawsuit does describe an altercation between Scruggs and Winslow, and the suit was dismissed in 2009, according to court records.
In 2014, with the fear of extortion apparently behind him, Winslow's reputation took a hit when the news media publicized details of an incident that took place the month after he was suspended for four games for violating the NFL's policy on performance-enhancing substances.
Then playing for the New York Jets, Winslow was detained by police Nov. 19, 2013, outside a Target store in East Hanover, N.J. A woman had called police and reported she thought she saw Winslow masturbating in his vehicle, according to court records.
Two open containers of Vaseline were on the center console of Winslow's car, but he denied he had been masturbating, according to court records. The woman declined to press charges, but police also found synthetic marijuana in the car, leading to a misdemeanor charge for which Winslow entered a program for first-time offenders.
Coincidentally or not, his NFL career was over.
'He was thinking of us'
Seated in the football stadium grandstands at Scripps Ranch High School, where Winslow starred after transferring from Patrick Henry High before his junior year, head coach Marlon Gardinera reflected on his relationship with Winslow.
Involved in youth sports when Winslow was in high school, Gardinera said he coached Winslow one summer in AAU basketball. "So talented he had already formed that chip on his shoulder," he said.
Earlier this summer, Gardinera said, he was thrilled when someone called on Winslow's behalf and said Winslow wanted to donate about $2,500 of workout equipment to the school. "So he was thinking of us," Gardinera said.
It was during this time that Winslow's behavior allegedly took a dark turn.
On May 24, he allegedly exposed himself to a 55-year-old woman who was gardening. Winslow took a 19.25-mile bike ride logged in his verified account on the Strava fitness tracking app on the same day, and the fitness record shows he passed along the same street on which the alleged victim lived.
The woman said the assailant arrived by bike and was wearing cyclist-style clothes. Winslow faces three misdemeanors, one for exposing himself and two trespassing charges.
This incident in question took place after Winslow allegedly raped the two homeless women and before he allegedly broke into the homes of the two elderly women.
He now is under house arrest in Encinitas after posting $2 million bail. But some members of the homeless community said they still fear him.
Standing near the entrance of the outdoor shopping center where Winslow allegedly raped a 54-year-old homeless woman in March, a 58-year-old homeless woman held a cardboard sign that read, "Anything helps! Thank you."
Referring to Winslow's alleged rapes, the woman said, "That could have been me."
Though she provided her name and age, the woman spoke to USA TODAY Sports on the condition she not be identified because she said she fears Winslow.
"You never know if the weirdo's got people backing him up" on the streets, she said.
Jane Doe 2, who according to testimony stayed at a hotel for more than two weeks paid for by a crime victims fund, was back on the streets in Encinitas on Monday. The woman sipped from a coffee cup and paced in front of bus stops less than a block from where she allegedly got into Winslow's Hummer on May 13.
How are you doing, a couple of her friends ask.
"OK," she said softly each time.
Winslow, in addition to retaining San Diego attorney Brian Watkins, has hired Harvey Steinberg, an attorney from Denver who successfully has represented several NFL players. The list of Steinberg's exonerated clients includes Brandon Marshall, a veteran wide receiver now playing for the Seattle Seahawks; Perrish Cox, a cornerback and return specialist playing for the Denver Broncos; Rolando McClain, a free agent linebacker who last played in the NFL in 2016; Bill Romanowski, the retired Pro Bowl linebacker; and Travis Henry, the retired Pro Bowl running back.
Winslow's defense team also includes a less-publicized member, Marie Little, a private investigator.
In 2016, Little pleaded guilty to four misdemeanor counts of unauthorized communication with prisoners for sending text messages and making calls to inmates while knowing they were in illegal possession of cell phones. She was sentenced to three years probation and as a result, Little said, lost her private investigator license. But Little said she now works under the license of Dennis Sesma, owner of DS Investigative Services in San Diego.
"I got the job done," Little said of her work in Winslow's case. "I found people that nobody could find."
Finding Winslow takes less work.
He is holed up in his $2.9 million house in Encinitas, where two weeks ago his wife, Janelle Winslow, declined comment to USA TODAY Sports. There were also two men assembling exercise equipment in Winslow's three-car garage. But there was no sign of Winslow or any equipment that was supposed to go to Scripps Ranch.
The morning Gardinera was scheduled to pick up the equipment at Winslow's house, the coach said, he received a text message that read, "Hey coach, I'm so sorry can we push this to next week? I will let you know ASAP when we can reschedule."
Winslow, it turned out, had been arrested the night before.
"Haven't heard a word" since then, Gardinera said. "But we all know things got progressively worse on their end."
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