NYC Bar Mimics Mattress Mack But Hedges on Prediction Market Instead of Sportsbook

Posted on: June 2, 2026, 11:09h. 

Last updated on: June 2, 2026, 11:09h.

Devin O'Connor @CasinoorgDevinO Read More
Expertise: Asia Pacific Gaming, Commercial Gaming, Legislation, Politics.
  • A NYC bar is offering free $100 tabs on the condition that the Knicks win Game 1 of the NBA Finals
  • The bar’s owner is hedging the promotion on the prediction market Kalshi

A bar in New York City is taking a page out of the playbook of Mattress Mack in offering free goods on the condition of the local professional sports team bringing home a championship.

NYC New York City bar Kalshi bet
Bartenders at The Jeffrey in New York City pose for a photograph for the bar’s social media. The Jeffrey’s owner is using the prediction market Kalshi to hedge a promo at the venue. (Image: The Jeffrey/X)

The Jeffrey is a watering hole on Manhattan’s Upper East Side. The bar is owned by attorney Andrew Freedman.

On Wednesday night, Freedman is promising to cover up to $100 of every patron’s food and drink tab. The caveat is that the New York Knicks must win Game 1 of the NBA Finals that night against the San Antonio Spurs.

Freedman is hedging the promotion on Kalshi, a prediction market that offers event contracts on sports. Freedman has purchased $5,000 in shares of the Knicks winning tomorrow night’s game in San Antonio to cover his possible bar tab.

We want our customers to feel the magic of this moment, but we’re a small business, we can’t just eat a full night’s revenue on a whim. Kalshi let us make the boldest possible promise to our customers and know we’re covered no matter what,” Freedman said.

Freedman says the Kalshi winnings would offset the bar’s revenue losses for the evening.

“If the Knicks lose, the bar collects abnormally high revenue from the promotion, having paid only a small premium for the peace of mind,” Freedman explained.

Promotions Hegde Sports 

Freedman certainly isn’t the first to use a sports bet to cover potential losses from his business’s promotion. Such advertising was made famous by Mattress Mack, the Houston furniture tycoon who owns Gallery Furniture.

Mattress Mack, or Jim McIngvale, in 2019, bet around $13 million on the Houston Astros winning the World Series. The bets were to cover a season-long promotion where customers who spent over $3,000 would qualify for a full refund should the Astros win the World Series.

The Astros lost in Game 7 to the Washington Nationals that year. Undeterred, Mattress Mack returned in 2022 with $75 million in bets on the Astros winning the World Series. Houston won the series 4-2 against the Philadelphia Phillies, meaning thousands of Gallery Furniture customers won big, too.

Kalshi Promotes Hedging 

Kalshi has defended its sports event contracts as financial instruments against critics who say the markets constitute sports gambling. The company says Freedman’s promotion proves its offerings provide investment strategies.

This is exactly what Kalshi contracts are designed. If you have risk tied to an event happening in the real world, this is what you can use prediction market contracts to help offset it,” a Kalshi representative told MarketWatch.

Freedman says this isn’t the first time he’s hedged a bar promotion on Kalshi. The Jeffrey ran a similar promotion during the Knicks’ Eastern Conference Finals against the Cleveland Cavaliers. During Game 4 of that series, Freedman discounted each bar tab by 1% for every point in the Knicks’ margin of victory. The Knicks won by 37 points.