What did O.J. Simpson think of Caitlyn Jenner before her transition?

Caitlyn Jenner
Photo Credit: Caitlyn Jenner’s Instagram (@caitlynjenner)

With O.J. Simpson back in the spotlight thanks to the new FX series “The People v. O.J. Simpson,” more details of the incarcerated sports star’s past are emerging. And one of those details is his relationship with transgender celebrity Caitlyn Jenner, whom Simpson knew as Bruce Jenner back in the ’80s and ’90s. Now, news stories are revealing what Simpson thought of Jenner before her transition.

For fans that don’t know, Kris Jenner was best friends with Simpson’s late ex-wife, Nicole Brown Simpson, who was allegedly killed by Simpson in 1994. Kris’ late ex-husband, Robert Kardashian, was one of the “dream team” lawyers who represented Simpson in the criminal trial in which Simpson was accused of murdering Nicole. However, he was found not guilty.


Simpson and Jenner knew each other throughout the ’80s and ’90s because of their mutual status as sports superstars, as well as Jenner’s marriage to Kris, whom Caitlyn married in 1991, before Caitlyn’s transition.

According to new media reports, Simpson’s former sports agent, Mike Gilbert, recently spoke out about Simpson and Jenner’s relationship and he says that Simpson never liked Jenner.


“O.J. always thought Bruce was weird and he never fit in,” Gilbert said. “O.J. hated Bruce. He thought he was really awkward.”

Gilbert spoke about a time in the ’80s when he and Simpson drove past Jenner on Sunset Boulevard and Simpson told Gilbert that he already knew that Jenner wanted to become a woman.

“This motherf—– wants to be a woman,” Gilbert said. “O.J. was looking straight at him and said, ‘I swear to God now look at him. You heed my words. That mother—— wants to be a woman.”

Simpson’s former manager, Norman Pardo, also spoke on the matter and claimed that Jenner’s then-wife, Kris, would try and ask her BFF Nicole to help her find friends for Jenner, which included trying to get Simpson to hang out with him.

“Bruce didn’t have any friends, so Kris would ask Nicole if O.J. could take him out and about,” Pardo said.

However, Gilbert says that Kris’ plan didn’t work at all with Simpson.

“He could just never stand him,” Gilbert said about Simpson.

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