Kellen Winslow II, once the highest-paid tight end in the National Football League as a key player for the Cleveland Browns, was sentenced on Wednesday to 14 years in prison for raping two women and sex crimes against three others.
The judge who sentenced him called Mr. Winslow a sexual predator who preyed on marginalized women.
One of the women whom Mr. Winslow raped was homeless at the time of the assault in 2018, and another previously testified that Mr. Winslow had raped her after she passed out at a house party in 2003. She was 17 at the time.
A third victim was hitchhiking in 2018 when Mr. Winslow gave her a ride and sexually assaulted her, she had testified.
At the sentencing on Wednesday in Superior Court in San Diego County, the judge, Blaine Bowman, said that Mr. Winslow, 37, had chosen victims — five altogether — who he believed would not report his crimes.
“I think that they’re brazen crimes, and he selected the most vulnerable victims he could possibly find in order to carry out his crimes and hopefully get away with it in his mind,” Judge Bowman said.
In exchange for avoiding a life sentence, Mr. Winslow pleaded guilty in 2019 to the rape of an unconscious victim and felony sexual battery charges.
Earlier that year, he was convicted of raping the 58-year-old homeless woman, along with misdemeanor charges of indecent exposure and lewd conduct.
The misdemeanor charges stemmed from Mr. Winslow’s exposing himself to a neighbor who was gardening and an episode at a Carlsbad, Calif., gym in 2018, when, a 77-year-old woman said, Winslow masturbated in a hot tub in front of her. Mr. Winslow had been released on bail and was awaiting trial for sexual assault at the time.
Four of the victims gave impact statements at the sentencing on Wednesday, including the woman who was homeless when Mr. Winslow raped her in Encinitas, Calif., a beach community north of San Diego, according to local news accounts.
The woman described having been in a constant state of fear since the sexual assault, checking under the bed and in closets, The Associated Press reported.
“It’s affecting my life every day and every night,” the woman said, according to the news service. “I don’t ever feel safe inside or outside. You brought so much damage to my life.”
Mr. Winslow, who is being held at a maximum-security jail in San Diego County, appeared remotely during the sentencing hearing and was wearing a mask. He declined to speak at the proceeding, citing the advice of his lawyers, who have contended that he suffered trauma from blows to the head while playing football.
Mr. Winslow spent nine seasons in the N.F.L. with the Browns, the Tampa Bay Buccaneers, the New England Patriots and the New York Jets. He signed a rookie contract with Cleveland for $29 million after the Browns selected him sixth overall in the first round of the N.F.L. draft in 2004.
His father, Kellen Winslow Sr., also a tight end, played for the San Diego Chargers and was inducted into the Pro Football Hall of Fame in 1995. But the career of the younger Mr. Winslow, a standout at the University of Miami, was marked by injuries, uneven play and off-field distractions. He was selected to the Pro Bowl just once.
In 2013, he was suspended for four games for violating the N.F.L.’s policy on performance-enhancing substances while he played for the Jets. He missed the 2005 season after sustaining a severe knee injury in a motorcycle crash.