Tuesday, May 5, 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

In this photo illustration, a mobile device displays the Kalshi logo while a laptop displays the webpage of the prediction market platform in Copenhagen, Denmark, on February 10, 2026. (Photo by Kristian Tuxen Ladegaard Berg/NurPhoto)

Leagues Weigh In on Future Prediction Market Regulation

Safeguarding integrity and protecting consumers were common themes.
The sun rises on the backside as horses work with their riders at Churchill Downs during Kentucky Derby week. April 30, 2026

Prediction Markets Finally Found a Sport They Can’t Offer

Here’s why you won’t see the Kentucky Derby on Kalshi or Polymarket.
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

CFTC: ‘Biggest Issue Is Manipulation’ in Sports Event Contracts

Michael Selig says his agency is in talks with “all the major sports leagues.”
Aug 23, 2025; Phoenix, Arizona, USA; A general view of the MLB logo before the start of a game between the Cincinnati Reds and Arizona Diamondbacks at Chase Field.

Sportradar Refutes Claims It Works With Illegal Betting Companies

The company is an integrity monitor for leagues including the NBA and MLB.

Featured Today

Cricket - Indian Premier League - IPL - Final - Royal Challengers Bengaluru v Punjab Kings - Narendra Modi Stadium, Ahmedabad, India - June 4, 2025 Royal Challengers Bengaluru's Rajat Patidar lifts the trophy as he celebrates with teammates after winning the Indian Premier League

How Private Equity Fell in Love With Indian Cricket

India’s U.S.-style cricket league has become a private-equity playground.
Kaitlin Oaks (left) from Tampa looks at photos with Layla Abutha from Tampa while attending Thurby at Churchill Downs during the week of Kentucky Derby on Thursday, April 30, 2026.
May 1, 2026

Kentucky Derby Is Courting Gen Z

Churchill Downs is mixing traditional splendor with a youthful atmosphere.
INDIANAPOLIS, INDIANA - MARCH 25: Caitlin Clark of the Indiana Fever sits on the baseline and makes photographs during the Indiana Pacers game against the Los Angeles Lakers at Gainbridge Fieldhouse on March 25, 2026 in Indianapolis, Indiana.
April 22, 2026

Why Athletes Are Moonlighting As Sports Photographers

Athletes are swapping courtside seats for sideline cameras.
Quinnipiac women's varsity rugby
April 21, 2026

The Death of Quinnipiac Women’s Varsity Rugby

The sudden decision at Ilona Maher’s alma mater left players blindsided.
Jul 25, 2025; East Rutherford, NJ, USA; FanDuel Sportsbook at Meadowlands Racing & Entertainment.

Warren Buffett Calls Sports Betting a ‘Tax on Stupidity’

The billionaire doesn’t like “things that make a sucker out of people.”
The logo of the 2026 NFL Draft is showcased at the big screen inside the theater Wednesday, April 22, 2026 from outside Acrisure Stadium in Pittsburgh, Pa.
April 23, 2026

NFL Draft Odds Chaos Pits Insiders Against the Market

There’s been plenty of line movement for the No. 2 pick.
Michael Selig, U.S. President Trump's nominee to serve as Commodity Futures Trading Commission (CFTC) chairman, testifies in a Senate Agriculture Committee hearing on his nomination on Capitol Hill in Washington, D.C., U.S., November 19, 2025.
April 27, 2026

Trump Calls It a ‘Casino.’ CFTC Chief Defends Role As Regulator

“We can’t have them be the Wild West. That’s why we’re taking action.”
Sponsored

What Is It Like to Run the Knicks?

Dave Checketts on his time running the Knicks & Jazz, Jordan war stories, and his investment strategy across major sports leagues.
An overall look at the newly opened MGM Grand Detroit sports betting & entertainment venue called BetMGM Sports Lounge at its casino in Detroit, Michigan on Wednesday, March 11, 2020.
April 21, 2026

‘Purely Gaming’: Inside the Tribal Fight Against Prediction Markets

A California tribal leader tells FOS “we have the truth on our side.”
April 9, 2026

College Athletes Are Ignoring NCAA Gambling Bans

“We were going to bet regardless,” says one former D-I athlete.
Jan 14, 2025; Washington, DC, USA; Sen. Richard Blumenthal, D-Conn., delivers remarks during a Senate Armed Services committee hearing on the expected nomination of Pete Hegseth to be Secretary of Defense on Tuesday, Jan. 14, 2025 in Washington, DC.
March 31, 2026

‘Astonishing and Appalling’: Senator Blasts MLB-Polymarket Deal

A Connecticut senator says prediction markets are part of an “addiction conspiracy.”
March 30, 2026

NFL Warns Prediction Markets Operators Over Vulnerable Bets

Ongoing litigation in the burgeoning industry has muddied the waters.