Kanye West’s Hotel Dream: Why Fathering Children with Paris Hilton Won’t Make Him a Hilton Hotel Tycoon

In a surprising turn of events, Kanye West has expressed regret over his past choices, specifically regarding his romantic life. A recent video clip circulating on social media showcases West reflecting on his relationship with Kim Kardashian and pondering what might have been had he chosen Paris Hilton instead.

Kanye’s Contemplation on Past Relationships

In the now-viral video, Kanye West candidly states: “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.“

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’s only power is to take your kids”pic.twitter.com/KZmPtxamRm

— Kanversation™️ (@TheKanversation) April 25, 2025

While the suggestion of Kanye and Paris forming a family and ruling the Hilton empire may seem intriguing, there’s a significant flaw in his hypothetical scenario.

The Reality of the Hilton Empire

The Hilton name continues to shine above hotels globally; however, the family itself has not possessed a controlling stake in Hilton Hotels for many years. Established by Conrad Hilton in 1919, Hilton Hotels evolved into the first international hotel chain and has become one of the most recognizable brands worldwide. After Conrad’s departure, his son, Barron Hilton, took over and expanded the business exponentially.

Under Barron’s leadership, Hilton Hotels transformed into a global powerhouse, introducing loyalty programs and operating casinos in Las Vegas. By the time of his retirement, the hotel chain was synonymous with luxury and quality on a global scale.

In 2007, however, Hilton Hotels Corporation was sold to Blackstone Group for a staggering $26 billion. Although the company went public again in 2013 and trades today under the ticker symbol HLT, Paris Hilton and her relatives have not held any meaningful ownership for nearly two decades—largely due to Barron’s decision influenced by family dynamics.

After years of public scrutiny surrounding Paris’s behavior, Barron Hilton made a significant alteration to his will in December 2007. He chose to donate a remarkable 97% of his estate, approximately $4.5 billion, to the Conrad N. Hilton Foundation, thereby reducing Paris and numerous other Hilton heirs’ expected inheritance substantially.

What If?

Kanye and Kim Kardashian began their relationship in April 2012, significantly after the Hilton empire’s ownership had changed hands. Hypothetically, if Kanye had pursued Paris instead, the Hiltons had already long lost control of the brand.

Interestingly, a photo from Vanity Fair’s 67th annual Best-Dressed List party—where Kanye was among the attendees—depicts Paris seemingly about to “bite” Kanye’s neck. This photograph was captured on September 11, 2006, a year prior to the sale of Hilton to Blackstone and just over a year before Barron changed his will. In an alternate universe where Kanye and Paris had connected romantically at that event, it is conceivable that they might now preside over a vastly different fortune, replete with their own stake in the Hilton empire.