O.J. Simpson photographed with judge who sentenced him, unaware of her identity

Judge Jackie Glass, who sentenced O.J. Simpson to up to 33 years in 2008, was photographed with him after his release — Simpson had no idea who she was.

Simpson smiled for photo with his sentencing judge, not knowing who she was

Judge Jackie Glass, who presided over O.J. Simpson's 2008 robbery and kidnapping trial in Las Vegas and sentenced him to up to 33 years in prison, died last week. In the days following her death, the Toronto Sun Crime reports, her family revealed a remarkable story: Glass and a group of friends had a chance encounter with Simpson at a restaurant after his 2017 parole — and the meeting ended with a photo of Simpson smiling alongside the very judge who had sent him to prison, entirely unaware of who she was.

"OJ loved beautiful blonde women, so my mom's friend baited him into taking a picture," Glass' daughter, Rachel Wolfson, wrote on social media. "He had no idea he was taking a photo with the judge who sent him to prison."

Glass appears in the photo alongside her friends, her other daughter Rebecca Wolfson — now a judge herself — and attorney Justin Randall. "I can't believe we kept this picture under wraps for six years," Randall wrote in response to the post.

Glass' husband, Clark County District Attorney Steve Wolfson, confirmed to the Las Vegas Review-Journal that Simpson never recognized who was standing beside him. "One night, Jackie went out to dinner with her friends and there's O.J.," Wolfson said. "And I don't think it was Jackie's idea, because it wouldn't be her idea. It was one of the girlfriends that she was with that said, 'Hey, why don't we go up and take a picture with O.J.?' He had no idea that the sentencing judge that sent him to prison was standing just a few feet away."

Simpson had been acquitted in 1995 of the 1994 murders of his former wife Nicole Brown Simpson and her friend Ron Goldman at his Los Angeles home, in one of the most widely followed criminal trials in American history. His defence team, led by attorney Johnnie Cochran, dismantled the prosecution's case — pointing to racist remarks made by LAPD Detective Mark Fuhrman and demonstrating that Simpson could not fit his hands into blood-soaked leather gloves recovered at the murder scene. Cochran's summary to the jury became one of the most quoted lines of the trial: "If the glove doesn't fit, you must acquit." Simpson was later found liable for both deaths in a subsequent civil trial.

His legal fortunes reversed in 2007, when he was arrested after holding two sports memorabilia dealers at gunpoint and robbing them at the Palace Station hotel and casino in Las Vegas. Simpson maintained he was attempting to recover personal sports mementos he said had been stolen from him.

A jury convicted him on all 12 counts, including armed robbery, kidnapping and assault. Glass, serving at the time as a Clark County District Judge, presided over the proceedings and handed down a sentence of 9 to 33 years in prison. Simpson was granted parole in 2017 and died in 2024.

The photograph, kept private for six years, surfaced publicly only after Glass' death — a final, quietly ironic footnote to one of the most scrutinized legal careers in Nevada history.

Source: Toronto Sun Crime