Kris Jenner & Corey Gamble's Trouble In Paradise Escalates With Big Payday Demand Rumor

By Afouda Bamidele on August 29, 2025 at 7:30 PM EDT

Kris Jenner & Corey Gamble attend Los Angeles Ballet Gala 2020
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Things are really not looking good for Kris Jenner and Corey Gamble!

The momager is reportedly on the verge of losing her relationship with the TV personality, and there appears to be no light at the end of that tunnel, considering his post-breakup plans.

Kris Jenner and Corey Gamble began dating in 2014, following her divorce from Caitlyn Jenner, and have remained inseparable until now. The duo currently has no kids together, nor did they ever get married.

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Corey Gamble Allegedly Going For A Big Payday From Kris Jenner

Corey Gamble and Kris Jenner at the 2024 Vanity Fair Oscar Party
CraSH/imageSPACE / MEGA

The duo's love story is gradually descending into chaos as they continue to argue, whether at Jeff Bezos and Lauren Sánchez's or at the recently concluded Cowboy Carter tour.

For the latter, Khloé Kardashian reportedly tried her best to diffuse the situation, but the feuding couple would rather let the world burn and turn around the frowns on their faces.

Now that the inevitable may happen at any time soon, sources report that Gamble has put a foolproof plan in place to mitigate his loss. As shared by a source:

"He feels he deserves a nice payday. He reasons he deserves it after having been Kris' protector, business partner, assistant, confidant, and lover."

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According to RadarOnline, the source added that Gamble sees himself as "the glue holding the family together during all their crises," so he deserves to leave with a substantial severance package.

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More Details Into The Reality Star's Safety Blanket

Corey Gamble is seen arriving at his hotel in Paris
Spread Pictures / MEGA

Gamble has reportedly had enough with Jenner's habit of constantly berating him in public, and at this point, he refuses to be his partner's doormat. As things are now, insiders noted that it is only a "matter of time before they go their separate ways."

Despite Jenner wanting to make things right with her partner, Gamble feels it is too late to mend fences. He reportedly just wants to get his share of Jenner's bounty and head out of the relationship.

The reality star reportedly stated that his career was on an upward trajectory as a talent manager when he met the Kar-Jenner matriarch in 2014, but he chose to keep that in the backseat for her.

"Now he just wants his fair share – or he'll be forced to find other ways to profit off the years when he was Kris' love slave," the insider added.

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Inside Jenner And Gamble's Clash In Venice

Kris Jenner and Corey Gamble
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Although Gamble arrived in Venice a day before the event and alone, he was eventually joined by Jenner, and they attended the wedding together.

The Blast shared that after the festivities, Jenner and Gamble set out to leave the event, but the momager had other plans, mostly involving her returning to her hotel without her boyfriend. 

Scenes by the dock were unpleasant, especially when Jenner became agitated at the point of boarding, stressing that she would really like to go back alone.

The couple finally resolved their logistic hassles and headed for their final destination, but not without evoking curiosity from fans about the state of their relationship.

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How It All Began For The Former E! Television Stars

Kris Jenner and Corey Gamble seen leaving dinner at Craigs Restaurant in West Hollywood, CA
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Things began as the perfect fairytale story for Jenner and Gamble, right after she got her heart shattered by a messy divorce from Caitlyn after decades together. 

As noted by PEOPLE, the duo met for the first time ever at Riccardo Tisci's birthday bash in Ibiza, which Gamble attended as Justin Bieber's manager. They stepped out for dinner months later, and the former celebrity manager agreed that he wanted more from his friendship with Jenner at the time.

The couple then jetted out to Mexico ahead of Jenner's 59th birthday and spent her actual birthday with a night out at 1 OAK Las Vegas. They finally debuted on the small screen the following year on "Keeping Up With The Kardashians," where Jenner's kids discussed the age gap between them.

Last year, on their tenth-year anniversary together, Jenner shared that Gamble really paid no mind to the dominant age gap between them when everything began, despite her own concerns. "I didn't get the age gap, and then he taught me that age is just a number," Jenner noted.

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Kris Jenner Allegedly Truncated Corey Gamble's Appearance On 'Yellowstone'

Kris Jenner and Corey Gamble leaving Le Grand Cafe at Grand Palais for Lauren Sanchez bachelorette party
Spread Pictures / MEGA

As noted by The Blast in 2023, the 69-year-old and her boyfriend got candid about her role in losing out on a role in the hit TV series, largely due to Jenner's jealousy.

As Jenner excitedly informed her kids about her plan for the next episode of "Yellowstone," Gamble interrupted, reminding her that she got in the way of his opportunity to appear in the project.

Jenner clarified that her hesitation stemmed from the thought that Gamble would go on the show to play the role of a character in a romantic relationship, which would not sit well with her.

The TV star's controlling ways have also unsettled some of her kids, especially Kourtney Kardashian, who suggested she try out therapy to release years of bottled-up emotions from the past.

Is this really the end of the road for Kris Jenner and Corey Gamble?

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