Kris Jenner labels infidelity 'my life's biggest regret'

Kris Jenner poses in a black dress and floral earrings in front of a white draped backdrop

By Nardine SaadStaff Writer

Oct. 26, 2023 1:12 PM PT

Kris Jenner has some regrets, but the biggest one is cheating on the father of her four children, Robert Kardashian.

However, if she didn’t do it, the famed “momager” never would have had her two other beloved children: model Kendall Jenner and beauty mogul Kylie Jenner.

“The Kardashians” star was wed to the late O.J. Simpson defense attorney from 1978 to 1991 but had a months-long affair with soccer player Todd Waterman during the union that yielded their four famous children: Kourtney Kardashian, Kim Kardashian, Khloe Kardashian and Rob Kardashian Jr.

In the opening of Thursday’s episode of the family’s Hulu reality show, Khloé — who is navigating a tricky relationship with her cheating ex Tristan Thompson — asked her mother why she cheated on her father (“You have four kids and your whole family, this whole thing”). And the “Keeping Up With the Kardashians” alum blamed it on the mind-set she had in her early 20s.

“I think being really young and dumb is something that plays into it,” she said, “because you don’t really understand the consequences of your actions.”

However, she couldn’t pinpoint for her daughter what Kardashian was doing that made her “look elsewhere” then, even after all this time.

“I don’t know, because he was such a great husband and such a great dad,” she said. “And I think that I fell into a situation where I thought that the grass was greener somewhere else. And I made a huge mistake. That’s like my life’s biggest regret.”

For those closely keeping up with the reality-TV clan, Jenner’s infidelity admission on Thursday’s episode isn’t new. In 2013, on the heels of her split from Caitlyn Jenner after 22 years of marriage, the reality star said that she regretted divorcing Kardashian.

“The one regret, if I had to do it over, would be divorcing Robert Kardashian,” Jenner said in a 2013 issue of New You magazine (via People). “But then there wouldn’t have been Kendall and Kylie, so that’s the way I look at it.”

Robert Kardashian was both Simpson’s best friend and a member of his vaunted defense-attorney “Dream Team,” despite having to reactivate his lapsed law license to join it. The football Hall of Famer, who was acquitted of murder in 1995, even served as an usher during Kardashian’s 1978 wedding to Jenner (née Kris Houghton).

But the 11-month trial of the century strained Kardashian’s relationship with his wife and resulted in death threats against their family. The lawyer also struggled with his loyalty to the Juice, as he affectionately called the athlete, and the perception of disloyalty to Simpson’s ex-wife, Nicole Brown Simpson, with whom Jenner had been close friends.

Jenner admitted to having an affair with Waterman in 1989.

“I constantly lied to Robert” during the affair, Jenner wrote in her 2011 autobiography, “Kris Jenner … And All Things Kardashian.” “I could not control myself.” Kardashian caught her and her lover meeting for breakfast — she thought he had her followed by a private detective — which led to a huge fight. This would go on for three months, with him catching them together three times.

He eventually filed for a divorce, and the split was finalized in March 1991. Jenner remarried a month later — less than a year after getting fixed up with Caitlyn Jenner on a blind date.

In a confessional interview during Thursday’s episode, Jenner said that she and Kardashian became “best friends” after they divorced. And they appeared to remain so until he died of esophageal cancer in 2003.

“We talked on the phone all day long, helped each other through things all the time. And I did have regrets. I thought, ‘Wow, what was I thinking?,‘” Jenner said. “So, I just want Khloé to be really careful when she makes these decisions and she has to let somebody go.”

But, the mother of six told her daughter, she was also thankful for those mistakes because ultimately they led to her having her two youngest children.

“You know, I’m not proud of the way that I behaved during that time. But you know what? Everything happens for a reason,” she said. “I really do live my life by thinking God has a plan. And without that whole thing happening, there never would have been Kendall and Kylie.”

Jenner sang a similar tune in her 2013 interview on the topic, saying: “Everything happens for a reason, and we learn from our mistakes. I thought I was so smart when I was young; I was fearless.”

She added that love is “nonnegotiable” in her life.

Jenner, who recited the same story on a 2020 podcast, has been with her current boyfriend, Corey Gamble, since 2014.