Shilo Sanders expected New York to be exciting and convenient. Instead, the son of NFL legend Deion Sanders says he has been caught off guard by how difficult it is to find a proper meal in the city—an unwelcome surprise as he searches for an apartment while an $11.89 million bankruptcy judgment hangs over his financial future.

New York was not what he expected

In a recent X video, Sanders admitted his early impressions of the city clashed sharply with what he imagined. He had pictured life in New York as effortlessly vibrant once he secured a place to stay, saying, “I didn’t know it was gonna be this hard to find food, bro, in New York. I’m thinking, ‘Oh, bro, if I get a spot in New York, it’s gonna be turning. It’s gonna be lit, bro.’”

His frustration isn’t that the city lacks restaurants, but rather that finding a substantial meal on short notice proved surprisingly limited. “I can go eat anywhere,” he explained. “All they say is they got a pizza place right there. That’s it.” That gap between expectation and reality—discovering that even grabbing a late-night bite felt more restrictive than anticipated—quickly tempered his enthusiasm.

Sanders is testing out New York as a potential home base after ruling out Florida locations like Downtown Miami and West Palm Beach due to steep rents and safety concerns. Beyond football, the city appeals to his broader ambitions in fashion, modeling, acting, music, and content creation. While his brother, Cleveland Browns quarterback Shedeur Sanders, has offered to cover the down payment on whichever home Shilo selects, Shilo remains responsible for the ongoing monthly payments—making rent and living space critical factors.

That financial reality has only compounded his skepticism toward New York. In a November 6 YouTube video recorded while getting a haircut, Sanders pointed to the city’s real estate market as his primary deterrent, criticizing the lack of square footage for the cost.

“Like, even if my budget is, I’m not even gonna say this is my budget, but you can go all the way up to $12,000 a month, and it’s despicable what they’re doing up there, bro,” Sanders said, questioning who normalized New York’s housing prices after seeing how little space even a five-figure monthly budget buys. Calling the market “outrageous,” he added that even apartments at that price point failed to offer enough room to justify the expense.

A judgment that will not go away

Sanders’ reluctance to lock himself into an exorbitant New York lease is closely tied to his unresolved legal and financial liabilities. The $11.89 million judgment stems from a 2015 incident at his Dallas high school when he was 15. John Darjean, then a school security guard, alleged that Sanders injured him after Darjean tried to confiscate Sanders’ phone under school policy—claiming Sanders elbowed him in the neck and punched him, causing nerve damage and incontinence. Darjean sued in 2016, and after Sanders failed to appear at the 2022 trial, a default judgment was entered against him.

Although Sanders has maintained he acted in self-defense—testifying during his bankruptcy trial that Darjean attacked him—Darjean’s legal team has countered with witness testimony, school findings, medical records, and a police report listing Sanders as a suspect in an aggravated assault.

Seeking to wipe out the debt, Sanders filed for Chapter 7 bankruptcy in October 2023. Darjean is contesting the discharge, arguing that under bankruptcy law, debts resulting from a “willful and malicious” injury cannot be erased. Following a trial in Denver from August 31 to September 4, Judge Michael E. Romero requested written closing arguments from both sides before issuing a decision.

The legal back-and-forth is now in its final stages:

• November 9: Darjean filed a 53-page closing brief urging the court to keep Sanders responsible for the debt and convert it into a nationwide federal judgment.
• December 10: Sanders’ attorney is scheduled to submit his closing argument.
• December 21: Darjean’s team faces its deadline to file a final reply.

The outcome carries massive stakes for Sanders’ financial future. If Judge Romero sides with Darjean, Sanders will remain on the hook for the full $11.89 million judgment plus interest. If Sanders prevails, most of the debt could be discharged, though the bankruptcy trustee can still liquidate non-exempt assets—adding to the $210,000 (roughly 1.8% of the judgment) Sanders has already surrendered to the estate. While he weighs a possible move to New York, the pending ruling will determine whether the $11.89 million judgment follows him for years to come.