
Imago
Jan 14, 2025; Portland, Oregon, USA; Brooklyn Nets point guard Ben Simmons (10) stands for the National Anthem before the game against the Portland Trail Blazers at Moda Center. Mandatory Credit: Soobum Im-Imagn Images

Imago
Jan 14, 2025; Portland, Oregon, USA; Brooklyn Nets point guard Ben Simmons (10) stands for the National Anthem before the game against the Portland Trail Blazers at Moda Center. Mandatory Credit: Soobum Im-Imagn Images
Kendall Jenner didn’t hold back during her Super Bowl commercial for Fanatics. She spun a joke around the ‘Kardashian curse’, and took a few jabs at her previous boyfriends. With Ben Simmons, Jenner said the former 76ers point guard “flopped right out of the league”. Clearly, the Australian hooper took exception. He partnered up with Sleeper, a competitor to Fanatics, to respond to Jenner.
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It was a “swift” response (you’ll understand if you watch the advertisement) from Sleeper, who also brought Tiffany Hadish in their latest advert. Her and Simmons pose as the “Ex Communicators” to resolve issues between former partners in the commercial. The former Nets guard certainly pointed at his own situation.
“Are your exes subbing you in commercials?” Ben Simmons says, hinting at Kendall Jenner taking aim at some of her previous partners in her latest advert. Simmons even asked for shared dog custody, referring to Jenner’s Doberman, Pyro, who also featured alongside her. As confirmed by the director, Trevor Free, the advert was a response to Simmons being “publicly shaded in a viral ad by his ex”.
After @BenSimmons25 was publicly shaded in a viral ad by his ex last week, he decided it was only fair to call @TiffanyHaddish and lawyer up.
Had an insanely fun time writing, directing and getting this out in five days for @SleeperHQ! pic.twitter.com/aCMKONRm2b
— Travon Free (@Travon) February 8, 2026
Furthermore, the $400 million company Sleeper made sure they delivered a response as soon as it was provoked. Free revealed it took him just five days to write and direct the entire campaign. They made sure Ben Simmons’ appearance generated the prompted intrigue as Kendall Jenner threw the first punch.
Simmons and Jenner started dating in 2018, with the latter confirming their relationship a year later. They didn’t date for long, with some outlets stating they had a sporadic relationship. But if there wasn’t a feud back then, there certainly is now.
And, unfortunately for Jenner, Ben Simmons wasn’t the only former partner who took aim at her.
Devin Booker takes a dig at Kendall Jenner
The entire point behind Jenner’s new campaign was to promote Fanatics Sportsbook. She didn’t reveal her Super Bowl pick in the advert, but did later reveal she was gunning for the New England Patriots. Well, they lost to the Seattle Seahawks in San Francisco, and Devin Booker was the happiest man.
He had previously argued with Jenner over her picking the Patriots. Reportedly, he placed a bet on the Seahawks to win. And once they did, D Book took a playful dig at the ‘Kardashian Kurse’ just like Jenner.
It wasn’t a well-produced advertisement. Devin Booker took to his Instagram stories and wrote, “Broke the Kurse”, pointing to him being one of Jenner’s ex-partners. Everybody noticed it. However, Booker and Jenner appear to be on good terms amidst rumors that they may have reconciled again.
That news hasn’t been confirmed by anybody else. They recently had a social media conversation, which prompted fans to believe so. But Jenner’s new advertisement has certainly encouraged a friendly war between exes.

