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Regrets. Kanye West has a few. But one of them is not what you were thinking.
Today, a video is making the rounds on Twitter in which Kanye can be heard giving the following monologue:
“Kim was Paris Hilton’s assistant. I should have had babies with Paris Hilton over Kim Kardashian. Could you imagine if I had kids with Paris Hilton how many hotels I’d have now? Think about that. The Hilton shit… So Kim’s only power is to take my kids. I had a baby with a fucking assistant bro. And then put her on Vogue. You can put no motherfuckin’ assistant on Vogue bro.“
Here’s an embed of the video:
Ye says he should have had babies with Paris Hilton instead of Kim Kardashian
“…Can you imagine if I had babies with Paris Hilton how many hotels I would have now?
Kim was like Paris Hilton’s Virgil….
If you have kids with a nanny, the nanny only power is to take your kids” pic.twitter.com/KZmPtxamRm
— Kanversation™️ (@TheKanversation) April 25, 2025
It is an interesting concept. Kanye and Paris ruling the Hilton empire with their children. But there’s just one little itty bitty teeny problem with Kanye’s plan.
The Hilton family hasn’t actually owned Hilton Hotels for a very long time.
(Photo by Johnny Nunez/WireImage)
The Hilton Empire
The Hilton name may still glow in gold letters above hotels around the world, but the family behind that name cashed out years ago. Founded by Conrad Hilton in 1919 with the purchase of a small hotel in Cisco, Texas, Hilton Hotels grew into the first international hotel chain and one of the most recognized brands in the world. After Conrad stepped down, his son Barron Hilton took over. Barron transformed Hilton into a global empire.
Under Barron’s leadership, the company expanded aggressively across the United States and internationally, pioneered the use of loyalty programs, and became the first major hotel brand to successfully operate casinos in Las Vegas. By the time Barron retired, Hilton Hotels was a powerhouse in both hospitality and gaming, with a reputation for luxury, consistency, and global reach.
In 2007, Hilton Hotels Corporation was sold to private equity giant Blackstone Group for $26 billion. The company later went public again in 2013 and now trades under the ticker symbol HLT. Today, Hilton Hotels is owned largely by institutional investors like Vanguard and BlackRock. Paris Hilton and her relatives have no meaningful ownership stake in the business, and haven’t for nearly two decades… partly because of Paris.
For much of his adult life, Barron Hilton was planning to leave his family empire to his family. Unfortunately for roughly two dozen extended Hiltons, that’s not what happened.
After years of being embarrassed by Paris’s public behavior in the early 2000s — the reality shows, the paparazzi photos, the leaked sex tape — in December 2007, two months after the sale to Blackstone, Barron made a dramatic change to his will. Instead of leaving his multi-billion-dollar fortune to his family, Barron decided to donate 97% of his estate, roughly $4.5 billion, to the Conrad N. Hilton Foundation. That move effectively cut Paris and dozens of other Hilton heirs out of a fortune they once expected to inherit. Two dozen people should have inherited around $190 million apiece. Instead the math worked out to around $5.6 million per person, pre-tax.
What Could Have Been
Kim Kardashian and Kanye started dating in April 2012. So if Kanye had instead started dating Paris in April 2012, by that point, the money and hotel empire would have been long gone already.
On the other hand. The photo I found for this article, where Paris is seemingly about to vampire-bite Kanye’s neck, was actually taken at Vanity Fair’s 67th annual Best-Dressed List party. A list that Kanye was included on. This party (and photo) took place on September 11, 2006. That’s a year before Barron decided to sell Hilton to Blackstone. And a year and three months before he changed his will. SO. With a slight twist of fate, had Kanye and Paris hit it off at this party and begun dating in September 2006. AND if Kanye somehow charmed Barron Hilton into a) not selling Hilton to Blackstone and b) not changing his will…. there actually is a universe where Kanye and Paris West could be sitting atop the $50 billion Hilton Hotel empire today.
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