Tuesday, May 26, 2026

Sports Betting Companies Holding Comic at Arm’s Length After Trump Rally

With his DraftKings deal in question, sources told FOS that Hinchcliffe’s agent has contacted other sports gaming companies.

Tony Hinchcliffe at Donald Trump rally.
Tony Hinchcliffe at Donald Trump rally, Oct. 27, 2024. Credit: C-SPAN

Before his appearance at former President Donald Trump’s rally in New York on Oct. 27, comedian Tony Hinchcliffe was quietly one of DraftKings’ most productive brand ambassadors. 

The promo codes Hinchcliffe offered up on social media and elsewhere drove referrals to DraftKings before his racist jokes—ones that weren’t dissimilar in tenor from his appearance at Tom Brady’s Netflix roast earlier this year—complicated that relationship. Front Office Sports reported Monday that DraftKings was reassessing its relationship, but the company has not definitively said it has cut Hinchcliffe, known as “Kill Tony,” loose. 

“They could be waiting for this to blow over,” said one longtime betting industry insider who was granted anonymity due to the sensitive nature of the subject matter. 

In the meantime, Hinchcliffe’s agent, Nick Nuciforo of United Talent Agency, had discussions last week with other sports betting and daily fantasy companies, two sources with knowledge of those discussions told FOS. Nuciforo did not respond to a request for comment before publication. 

“Nobody wants to work with him until the news cycle dies down,” one of those sources said. 

There continues to be fallout from Hinchcliffe’s set. Several major Puerto Rican celebrities who had not previously weighed in on the election endorsed Harris, while there is some evidence that Harris’s standing among Puerto Rican and Latino voters has improved in recent days. 

Major companies that utilize brand ambassadors have been quick to distance themselves from athletes and celebrities facing controversy, including Apple cutting ties with then-Texans quarterback Deshaun Watson in 2021 after he was accused of sexual misconduct in a series of lawsuits. 

Sports betting and daily fantasy companies are no different, although they operate in the political sphere at the state level in ways many industries do not.

“Gaming companies will support both sides of the aisles in different states to get more favorable gaming regulations or licensing deals,” another veteran gambling industry employee said. 

DratKings is in a tough spot with Hinchcliffe. Publicly terminating his deal due to comments at the Republican presidential candidate’s rally would play well in blue states, but may not be viewed the same by politicians in red states. 

DraftKings currently operates in 26 states and, along with FanDuel, has dominated the sports betting market since the Supreme Court opened up state-sanctioned sports betting nationwide in 2018. DraftKings and FanDuel control about 70% of the legalized sports betting market in the U.S. A major factor in both companies’ rise is sports betting was maneuvering the political and legal landscape from the rollout of daily fantasy about a decade ago. 

And Hinchcliffe wasn’t DraftKings’ only recent ambassador headache. Last week, betting analyst Taylor Mathis locked her account and—like Hinchcliffe—removed references to DraftKings in her social media accounts after she was accused of being involved in a crypto pump-and-dump scheme. 

“DraftKings is probably one of the most recognizable brands in the country right now,” one of the veteran insiders said. “If I was them, I’d have no ambassadors.”

This field is for validation purposes and should be left unchanged.

Sign up for
The Memo Newsletter

Get the biggest stories and best analysis on the business of sports delivered to your inbox twice every weekday and twice on weekends.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

U.S. Senator Richard Blumenthal (D-CT) speaks with the press after the Republican-controlled U.S. House of Representatives passed bipartisan legislation to fund Department of Homeland Security agencies including the Secret Service and Transportation Security Administration in a move to end the partial shutdown that has gripped their operations for nearly 11 weeks, on Capitol Hill in Washington, D.C., U.S., April 30, 2026.

Critics Warn Kalshi and Polymarket Risk a Juul-Style Reckoning

Their advertising methods came under fire from lawmakers this week.
Mark Cuban

Mark Cuban: ‘Betting Isn’t the Problem’

These wagers have been behind the recent MLB and NBA gambling scandals.
Jun 12, 2025; Washington, DC, USA; Gov. Tim Walz (D-MN), left, alongside Gov. JB Pritzker (D-IL), right, and Gov. Kathy Hochul (D-NY), not shown, testify before the House Committee on Oversight and Government Reform during a hearing on state immigration enforcement policy in Washington, D.C., on June 12, 2025.

Trump Admin Sues Minnesota to Block Prediction-Market Ban

Minnesota is the sixth state the federal regulator has sued.
DraftKingsApp

DraftKings Cofounder: Kalshi Is Years Away From Competitive Product

Kalshi responded with a gif from the movie “Mean Girls.”

Featured Today

May 24, 2026; Evanston, IL, USA; Northwestern Wildcats attack Kathryn Ratanaproeksa (13) shoots against the North Carolina Tar Heels during the first half at Martin Stadium

Can Women’s Lacrosse Buck the Trend in College Sports?

The sport is fighting to prove its worth in the revenue-sharing era.
May 22, 2026

Big Money on the Line on Premier League’s Final Day

Arsenal has won the title, but millions are still at stake.
Texas State mascot
May 22, 2026

Mascot-Reveal Videos Are the Newest College Sports Tradition

Student mascot unmasking videos are going mega-viral.
Charlie Pliner and Nikolas Rohrmann
May 22, 2026

How 2 Brown Undergrads Became Sports Dealmakers

An experimental project turned into a permanent course and business deal network.

Sportradar Hit With Lawsuit Over Alleged Illegal Gambling Ties

The suit alleges investors were harmed by shady overseas business conduct.
exclusive
May 14, 2026

Polymarket’s Soccer Spree Continues With Serie A Deal

It’s the third big soccer deal Polymarket has reached this year.
May 9, 2024; Columbus, OH, USA; Sports are shown on TVs behind the bar as guests enjoy the grand opening of DraftKings Sports & Social in the Short North. Though there are no on-site betting windows, eligible customers can place bets through the DraftKings app.
May 15, 2026

Gambling Layoffs Pile Up As Sports Betting Industry Recalibrates

Penn Entertainment headlines three companies with layoffs this week.
Sponsored

The Hidden Economy of Race Weekend

Learn more about the Vintage Flying Museum and how Spectrum Business is helping them achieve their business goals while fueling their dreams.
Kalshi's logo is displayed on a smartphone placed on a reflective surface onto which a betting curve is projected in Creteil, France, on March 9, 2026, during a major scandal and a $54 million lawsuit concerning bets related to recent strikes in Iran. (Photo by Samuel Boivin/NurPhoto)NO USE FRANCE
May 13, 2026

N.M. Tribes Claim Kalshi Sports Markets Violate Federal Law

The suit cites the same law a Wisconsin judge said tribes can pursue claims over.
May 8, 2026

DraftKings, FanDuel Push Further Into Prediction Markets

“It’s one of our fastest to profitability business lines we’ve ever launched.”
FanDuel
May 6, 2026

FanDuel CEO Pushed Out After Five Years Amid Stock Slump

Shares of Flutter, FanDuel’s parent company, are down more than 50% this year.
Dave Checketts
May 6, 2026

Former Knicks Pres: Leagues, Sportsbooks Have Gotten Too Cozy

“I’m not sure that’s a good thing, this coziness that we’ve established.”