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Weird Things About Kris Jenner’s Marriages

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Kris Jenner has spent decades running the family business, but her own marriages read like the strangest subplot the Kardashian-Jenner saga never turned into an episode.

Long before she was negotiating E! contracts or shaping her daughters’ brands, Kris Jenner was working through two marriages that ended in very different but equally messy ways. One collapsed under an affair and a frozen set of credit cards. The other ran for 22 years as something that looked, from the outside, more like a business partnership than a romance. Here’s what actually happened.

• Kris had an affair with soccer player Todd Waterman in 1989 while married to attorney Robert Kardashian, a decision she later called one of the biggest regrets of her life; the divorce was finalized in March 1991.
• She married Olympic decathlete Bruce Jenner just one month later, in April 1991.
• During their 22-year marriage, Kris managed Bruce’s career, building a business around motivational speaking, workout equipment, and eventually reality television, before the couple separated in October 2013 and filed for divorce in September 2014.

The Affair That Ended the Kardashian Marriage

Kris married Robert Kardashian in 1978, and the two built a life together that produced four kids and, eventually, an entire media dynasty. But by the late 1980s, Kris has since admitted, restlessness set in. In 1989 she began an affair with soccer player Todd Waterman, something she’s publicly described as one of the biggest regrets of her life, driven less by unhappiness and more by plain boredom.

Robert found out. His response was blunt: he froze her credit cards and filed for divorce. The split became official in March 1991, closing out a marriage that had, on paper, looked stable for more than a decade. Kris’s daughters have addressed the fallout of that era in their own ways over the years — Khloe Kardashian’s own complicated history traces back in part to how the family reorganized after that split.

A One-Month Turnaround

What makes the timeline genuinely strange is the speed of it. Kris’s divorce from Robert Kardashian was finalized in March 1991, and by April 1991 — just one month later — she had already married Bruce Jenner. There was almost no gap between the two chapters of her life, a detail that has fueled plenty of speculation over the decades about how the relationship with Bruce actually started.

Despite the abrupt exit from her first marriage, Kris and Robert didn’t become estranged. The two remained unusually close, functioning as frequent confidants and co-parents right up until Robert’s death from esophageal cancer in 2003. That continuity stood in contrast to how bitterly her second marriage would eventually end.

Manager First, Wife Second

Kris’s 22 years with Bruce Jenner were defined less by romance than by business architecture. She effectively became his manager, steering him from Olympic decathlon fame into motivational speaking gigs, workout equipment endorsements, and ultimately the reality television empire that would define the family. Critics and longtime observers of the family often pointed out how transactional the marriage looked from the outside — branding first, partnership second.

Long before they officially separated in October 2013, Kris was living at the family’s Calabasas mansion while Bruce rented a beach house in Malibu.

That physical separation — living in two different homes years before the paperwork caught up — is one of the clearest signs of how far apart the marriage had already drifted by the time it became public. The formal divorce filing didn’t come until September 2014, nearly a year after the split was announced.

The Fallout After the Transition

The divorce turned considerably more acrimonious after Bruce’s 2015 gender transition to Caitlyn Jenner. Caitlyn’s 2017 memoir, The Secrets of My Life, alleged that Kris had long known about her identity before the transition became public — a claim Kris flatly denounced as fabricated. The public back-and-forth added a bitter postscript to a marriage that had already ended, in practice, years earlier. It’s the kind of split that mirrors other celebrity relationships that curdled from partnership into open dispute once the cameras and the lawyers got involved.

By 2018, Kris had settled into a long-term relationship with talent manager Corey Gamble, who is 25 years her junior — a pairing that has kept fans and tabloids speculating for years about whether she’ll ever walk down the aisle a third time. So far, she hasn’t, and given how her first two marriages played out, it’s not hard to see why she isn’t in a hurry.