The surprise plea came right before the start of the ex-NFL tight end’s retrial on six felonies related to the two incidents, including rape, kidnapping and sodomy.
“I’m sorry. I’m just not thinking very clearly,” Winslow told the judge in San Diego County Superior Court, before asking for more time and eventually entering the guilty pleas.
The 36-year-old former pro-footballer in June was found guilty of the May 2018 rape of a 58-year-old homeless woman he befriended in Encinitas.
He was also convicted of indecent exposure and lewd conduct for incidents involving two other women.
In June a California jury had convicted former NFL player Kellen Winslow Jr. of raping a 58-year-old homeless woman but was unable to break a deadlock on eight other counts and a judge declared a mistrial on those charges.
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Ex-NFL player Kellen Winslow Jr was arrested in San Diego on Thursday and charged with a number of felonies, including rape, sodomy, burglary, indecent exposure, and […]

The judge previously denied a defense motion to dismiss the undecided charges involving the alleged rapes of a 54-year-old hitchhiker and an unconscious teen.
The San Diego County Superior Court jury on found the son of a Hall of Famer guilty of a 2018 attack on the homeless woman in his picturesque beach community of Encinitas, north of San Diego.
The jury also found the former tight end — at one point one of the highest-paid players in the NFL — guilty of indecent exposure and lewd conduct involving two other women, but jurors found him not guilty of one count of a lewd act.
At the time the jury told the court it was deadlocked when two jurors held out on one of the rape charges and the sodomy charge.

Kellen Winslow Jr. [seen left with the New York Jets and right with the Cleveland Browns],  was charged in June 2018 with kidnapping, raping two women aged 56 and 59. he also faced two counts of burglary with intent to rape, with the victims aged 71 and 86

The second raft of sexual assault charges against Kellen Winslow Jr included allegations by a woman who said Winslow raped her at a San Diego house party in 2003 when she was a 17-year-old high school student and he was 19 and home from college for the summer. Another victim was a hitchhiker who accused Winslow of picking her up in 2018 and raping her in his hummer

The charges on which the jury deadlocked include allegations by a woman who said Winslow raped her at a San Diego house party in 2003 when she was a 17-year-old high school student and he was 19 and home from college for the summer.
A hitchhiker also accused Winslow of picking her up in 2018 and raping her in his hummer. By the terms of the plea deal, that charge was reduced to sexual battery, with Winslow admitting he touched the woman in an intimate area while she was restrained.
Winslow  had previously pled not guilty to the charges. His attorney, Gretchen von Helms, had said the encounters were consensual.
Five women took the stand at the trial this summer, and three of them were expected to testify again.
Prosecutor Dan Owens praised the victims’ bravery and said “it was important to me to make sure that that truth was heard.”
“It was important to me to make sure that [Winslow] was held accountable for each one of those crimes,” Owens said.
In exchange for his plea, the court agreed to highly reduced sentence of 12 and 18 years in prison for the two charges, and dismiss the others.
Winslow’s attorneys will argue during his sentencing on February 19, 2020 that their client suffers from a brain injury from his football days and a motorcycle accident.
Before entering his plea, Winslow repeatedly looked back at his father, legendary San Diego Chargers tight end and Pro Football Hall of Famer, Kellen Winslow Sr.
As he left the courtroom, he reached an arm out to his dad, who responded by touching his fist to his heart.
Winslow, who also played for the Cleveland Browns, Tampa Bay Buccaneers and New England Patriots, was with the Jets in 2013.