Ex-NFL tight end Kellen Winslow II, who committed sexual offenses against five women in northern San Diego County, is slated to be sentenced Wednesday to 14 years in state prison.
The 37-year-old son of former San Diego Chargers legend Kellen Winslow agreed to the 14-year sentence last month through a new plea deal that had him admitting to assault with intent to commit rape in connection with one of the victims.
The younger Winslow had already been convicted in a 2019 jury trial of rape, indecent exposure and other crimes involving three women, but the jury hung on counts involving the other two victims. Winslow later pleaded guilty to counts related to the other two women and was facing up to 18 years in prison until the new plea agreement was reached in February.
On the original charges, he faced a potential life sentence.
In his trial, a Vista jury convicted Winslow of raping a 58-year-old homeless woman — Jane Doe 2 — in May 2018, exposing himself later that month to Jane Doe 3, who was gardening in her front yard in Cardiff, and touching himself in front of a 77-year-old woman — Jane Doe 5 — at a Carlsbad gym in February of 2019. The Carlsbad incident occurred after Winslow was arrested, charged and released on bail.
The jury could not reach a consensus on whether Winslow raped a hitchhiker in 2018 — Jane Doe 1 — or a 17-year-old girl — Jane Doe 4 — at a Scripps Ranch house party in 2003, paving the way for a second trial. Winslow entered his guilty pleas on the day the retrial was set to begin.
Deputy District Attorney Dan Owens said at trial that none of the five women knew each other, yet their accounts yielded common details and similar physical descriptions of the suspect.
Winslow’s attorneys told jurors that the charged incidents were either consensual or never occurred at all.
Winslow II grew up in San Diego and attended Patrick Henry and Scripps Ranch high schools before heading to the University of Miami. His NFL career included stints with four NFL teams between 2004 and 2013, and a Pro Bowl appearance in 2007.