O.J. Simpson had a long-standing relationship with the Kardashian family, well before Robert Kardashian joined his defense team for the infamous murder trial. 

Simpson, who died on April 10 after a battle with cancer, was long-time friends with Robert, the father of Kourtney, Kim, Khloe and son Robert. They later became household names thanks to their reality series, "Keeping Up with the Kardashians."

According to Slate, Simpson and Kardashian first met in college in 1967 at the University of Southern California, then became closer three years later after meeting at a mutual friend’s tennis court.

The outlet also reported that through Robert, Simpson met his business manager, Leroy "Skip" Taft, who helped him transition from NFL star to Hollywood personality.

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Kardashian met and married Kris (born Kristen Mary Houghton), and their friend Simpson met Nicole Brown while she was a waitress at The Daisy in Beverly Hills, marrying her in 1985 after divorcing his first wife, Marguerite.

"Nicole brought O.J. a lot of happiness — you could see it. She lit up his life," Kris told Slate in 2016. "They were golden together."

The foursome were close and began starting families. In her 2011 memoir, "Kris Jenner … and all things Kardashian," Kris wrote that Simpson came to visit her and Robert in the hospital after the birth of their first daughter, Kourtney. 

Simpson had two children with Nicole, Sydney and Justin. He was also a father to three children with ex-wife Marguerite, Arnelle, Jason and Aaren. 

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In a 2009 interview with Howard Stern, Kim recalled, "Every spring break we would go to Cabo San Lucas, Mexico" with Nicole.

Khloe added in the same interview she remembered Nicole being "incredibly sweet."

In a 2009 episode of "E! True Hollywood Story," Khloe recalled, "O.J. was always our Uncle O.J., Nicole was my Auntie Nicole."

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Robert and Kris divorced in 1991. A year later, in 1992, Nicole and O.J. divorced, following a documented history of abuse from the "Naked Gun" star. Kris noted in her memoir that had known that Nicole had been struggling in her marriage to Simpson, but hadn’t wanted to overstep, so she never asked about it, "which would become one of [her] biggest regrets."

In 1994, Simpson was arrested for the murder of Nicole and waiter Ron Goldman and enlisted Robert to be part of his legal team, putting a major strain on the once-friendly exes and their children.

The FX series "American Crime Story: The People vs O.J. Simpson" depicted a scene in which Simpson threatened to kill himself in Kim’s bedroom at Robert’s house.

Many assumed the scene to be complete fiction, but in a 1996 interview on "20/20" with Barbara Walters, Robert stated that Simpson had indeed been in Kim’s room with a gun, looking at photos of Nicole and his children.

He told Walters he had prayed with Simpson after he threatened suicide, and Robert begged him not to, saying, "I could never walk in this room, my daughter couldn’t sleep in this bed. She’d know what happened."

On "The Late Late Show with James Corden," Khloe said it was actually her room, not Kim’s, where Simpson’s suicide threat happened. 

Robert died in 2003 from esophageal cancer, but the memories of the trial still loomed over the family.

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Kris described the divide as "devastating" to the family in a 2009 interview on "Dr. Phil," saying, "You have Robert Kardashian on the defense team defending [O.J.’s] team, and you have me, my girlfriend’s dead. It was a very difficult situation and what we needed to do was band together as a family and decide that this isn’t going to tear us apart."

She also revealed, "Right before the trial started, Robert sat down and wrote us a handwritten letter and just said, 'Look, I know you don't agree with what is going down here, but this is what I have to do for my friend. He believed in what he was doing and he was asking us for his support."

The Kardashian girls, Kourtney, Kim and Khloe, were just children at the time of the trial, but they felt caught in the middle.

"My mom was extremely vocal on her feelings — she believed that her friend was murdered by him, and that was really traumatizing for her," Kim told David Letterman in 2020. "And then we'd go to my dad's house, and it was a whole other situation there."

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In an interview with GQ last year, Kim recalled, "My dad pulled Kourtney and me out of school. He said, ‘I want you girls to witness a piece of history and what a trial is like.’"

She continued, "We walked in and saw my mom sitting on the other side. She said, ‘You’re supposed to be in school. What are you doing here?’ Kourtney and I didn’t even look at her."

In 2009, Kim explained to Howard Stern that she and Kourtney had tended to side and spend time with their dad at the time, "because we felt like my mom had remarried so fast, and it kind of broke my dad’s heart, and she moved on, so we sided with my dad no matter what it was."

Khloe added, "I know for us as kids, it was very hard. I know for me personally, I just felt like, I was at my mom’s I couldn’t really talk about my dad. if I was at my dad’s, I couldn’t talk about my mom."

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Simpson was acquitted on October 3, 1995, and a short time later, he and Robert stopped being friends. After the verdict, Kim recalled her dad looking "shocked."

When asked about the fallout between her dad and Simpson, Kim told Howard Stern, "I think so, he kind of kept it away from us. I mean that was like, Uncle O.J., and we’d see him all the time, so after that, I remember the day he got out of jail, I went to his house with my dad and said hi to them, and then after that I don’t think we saw him again. I think they had a falling out." 

Khloe shared that her parents and step-dad became friendlier following the trial, telling Howard Stern, "After the OJ trial was done, they became best friends, my dad and my step-dad played golf together, it was fine, but during the trial, it was awful for us kids."

The Kardashian girls revealed that over time, their friendship with Simpson and Nicole’s children faded.

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In 2009, Khloe mentioned on Howard Stern that she had been "best friends" with their daughter Sydney, but neither she nor Kim spoke with her much anymore.

In 2019, Kim shared on the "FoodGod: OMFG" podcast with her friend Jonathan Cheban that she was still "somewhat friendly with his children."

"I don’t really talk to them, but I did connect with his son a few years back, and I just have respect for them, and their lives must be extremely hard to really go through that. I always try to keep to myself on that issue and not really bring anything up for them," she said.

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However, in 2021, Kim came under fire after she made a joke on "SNL" that referenced Simpson and the murder.

"It’s because of [my father] that I met my first Black person. Want to take a stab in the dark at who it was?" she said during her monologue. "I know it’s sort of weird to remember the first Black person you met, but O.J. does leave a mark or several, or none at all. I still don’t know."

After the episode aired, Nicole’s sister, Tanya Brown, told TMZ the joke was in "poor taste," adding, it was "beyond inappropriate and insensitive."

During her "FoodGod: OMFG" appearance, Kim also revealed the last time she and her sisters saw Simpson, sometime before his 2008 robbery case.

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Kim said, "I think the last time I saw him was in Miami . . . me, Kourtney and Khloé were in Miami in a club, and we ran into him in the VIP section. But it was like behind a stage or something. I don’t even know what club it was at. We all, I think, started crying. It was emotional, I think."

Though the families have essentially parted ways, the Simpson-Kardashian connection has lingered over the years.

As "American Crime Story: The People vs O.J. Simpson" reignited interest in the trial and Simpson’s history, rumors resurfaced that O.J. was Khloe’s biological father, not Robert.

On an episode of "Keeping Up with the Kardashians" in 2018, they confirmed that Khloe was indeed Robert’s daughter after doing an ancestry DNA test that showed she was "58 percent European, 41.6 percent Middle Eastern."

In the episode, Kourtney joked, "You are my sister!" Kourtney said, adding, "If you weren't Middle Eastern at all, we would be in big trouble."

Simpson also denied the allegations he was Khloe’s father, telling the "Full Send" podcast in 2022, "The rumor ain’t true. It’s not even anywhere close to being true."

"People have their types, right? I always thought Kris was a cute girl. She was really nice. But I was dating supermodels," he added.

He also denied the rumors years ago on his X, formerly Twitter, page, saying in a video, "Bob Kardashian, he was like a brother to me. He was a great guy," Simpson said in his third Twitter video. "He met and married Kris and they really had a terrific time together, when they were together. Unfortunately, that ended. But I never — and I want to stress, never in any way, shape, or form — have I ever had any interest in Kris romantically or sexually — and I never got any indication that she had any interest in me."

After calling the claims "bogus, bad, and tasteless," he said, "Khloe, like all the girls, I am very proud of, just like I know Bob would be if he was here. But the simple fact of the matter is that she is not mine."