Also: Bill Simmons’s proxy bet problem.  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌

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September 2, 2026

One week after Front Office Sports first reported that The Athletic is in serious talks with Kalshi on a potential sponsorship deal, New York Times staffers are speaking out. On Wednesday, The NewsGuild of New York sent a letter to the publishers and editors of The Athletic and its parent company, The New York Times, demanding the deal not come to fruition.

—Ben Horney and Ryan Glasspiegel

 

First Up

  • First at FOS: The Massachusetts Gaming Commission is looking into Bill Simmons’s admission that he had his daughter’s boyfriend place proxy bets for him on his FanDuel account.

  • Exclusive: Trey Wingo is reuniting with former ESPN colleagues Merril Hoge, Damien Woody, and Mark Schlereth to launch The OG Football Show.

  • Exclusive: Daniel Jeremiah is relaunching his Move the Sticks podcast as a solo show with ESPN and Omaha Productions.

  • Tony Romo has pleaded no contest to OWI and indicated he plans to return to CBS. The network placed its top NFL analyst on indefinite leave following his July arrest.

 

New York Times Union Demands Company Abandon Kalshi Talks

New York Times Union Demands Company Abandon Kalshi Talks

Carlo Allegri-Reuters

Unionized New York Times staffers are speaking out against a potential partnership between The Athletic and Kalshi.

The NewsGuild of New York—the labor union that represents more than 2,000 Times workers across three different units—sent a letter Wednesday to Times owner and publisher A.G. Sulzberger, Athletic publisher David Perpich, and senior editors at The Athletic and its parent company demanding that the prospective sponsorship agreement not go through. 

The letter was unanimously approved by the Times Guild Unit Council and The Athletic’s contract action team.

“We don’t comment on rumored deals,” a Kalshi spokesperson tells Front Office Sports. 

“Millions of people use prediction markets like Kalshi to view the forecasts on what’s happening in the world. They’re a great complement to news sites like The Athletic and The New York Times,” the spokesperson added.

Spokespeople for The Athletic and The New York Times did not immediately respond to requests for comment. 

FOS reported last month that the prediction-market platform and The Athletic were in advanced talks. Kalshi and its rival Polymarket have been in an arms race for customer acquisition even as lawsuits in states including Nevada and New York have threatened their ability to offer sports event contracts. Last week, the 9th Circuit, an appeals court, ruled Nevada can enforce its gambling laws against Kalshi—a decision that sets up an anticipated U.S. Supreme Court showdown. The Trump Administration’s Commodity Futures Trading Commission (CFTC) has been adamant that prediction markets are legal and has sued nine states that have attempted to block sports event contracts. 

In the letter, obtained by FOS, unionized workers at the Times say they are “deeply concerned” by the potential Kalshi deal. They note the event contracts offered by Kalshi “have been described by New York Officials in our reporting as an ‘illegal operation.’”

“Any partnership between Kalshi and The Athletic would threaten our journalistic independence across the company,” the letter says. “Despite management’s claim that The Athletic and The New York Times are separate business entities, the journalism and the work are intertwined, as any reader can see.”

Any agreement that involves more than Kalshi buying advertising space, especially one which “might integrate this product into The Athletic’s journalism,” could make readers question the outlet’s independence with regard to prediction-market reporting, the letter says.

“New York Times publisher A.G. Sulzberger has said that journalistic independence is the ‘core value’ that “answers the question of why we’re deserving of the public trust,” the letter says. “We call on the company to live up to that commitment and abandon this deal.”

Times reporters and other editorial staff have been unionized for more than 80 years. The New York Times Company bought The Athletic in 2022 for $550 million, and in January 2025, a group of roughly 200 editorial workers at the sports subscription site said they planned to unionize and asked the Times to recognize them as part of the Times Guild. A few days later, leadership at The Athletic responded, saying “the best approach” is to have a separate bargaining unit, not to have the Times Guild absorb editorial workers from The Athletic. As of this March, the Times Guild was still trying to get The Athletic’s employees into the union. In May, Times senior editor Jim Luttrell told Fox News “there is no reason they shouldn’t be in the union.”

The Athletic’s sponsorship deal with BetMGM expired earlier this year. FOS asked Austin Meek, a senior writer who covers college sports and is on The Athletic’s bargaining committee, whether the union opposes traditional sportsbook partnerships as well as prediction-market integrations.

“The BetMGM deal preceded NYT’s ownership of The Athletic,” Meek said. “The Times runs ads from a large range of companies, but any deal that integrates an advertiser’s marketing and products directly into our news coverage and journalistic content is concerning to us. We’re also mindful that our own New York Times reporting, by Times journalists, has shown that legal experts and government officials have significant concerns about the legality of Kalshi’s operations.” 

In addition to its bevy of sponsorships across sports—most recently with the US Open—Kalshi has news-network integrations with CNN and CNBC. Under those agreements, the news networks incorporate Kalshi data into broadcasts, among other forms of collaboration. 

 
FRONT OFFICE SPORTS LIVE

Netflix’s Elle Duncan to Join Tuned In

After nine years at ESPN, Elle Duncan is ushering in a new era as Netflix’s lead host for sports and live events while also serving as the studio host for USA Sports’s inaugural WNBA coverage. From anchoring SportsCenter to leading acclaimed coverage of women’s basketball’s biggest moments, Duncan has become one of the industry’s most influential and versatile broadcasters.

Now, you’ll have the chance to hear from her firsthand as she takes the Tuned In stage this October.

Join the conversation as we unpack how the sports media landscape is evolving—and what it takes to thrive across streaming, broadcast, and the next generation of live sports.

If you care about where sports media is headed, this is where you need to be. Secure your ticket now.

 

Around the Dial

Kirby Lee-Imagn Images

  • The Athletic’s Mike Silver told The Tom Tolbert Show that he expects his former colleague Dianna Russini to return to the sports media space soon, albeit likely not as an insider.

  • Netflix has revealed its first images of Pat McAfee playing a drill instructor in the upcoming Peter Berg film The Mosquito Bowl.

  • Former NFL quarterback and ESPN analyst Chase Daniel is teaming with Bussin’ With The Boys to launch a new Sunday NFL show called The First Read.

  • Following the demise of Main Street Sports Group’s FanDuel Sports Network, the NBA’s Cavaliers have reached a deal to stream their local games on DAZN.

  • Former NFL Pro Bowler Richie Incognito and Super Bowl champion Christian Fauria are launching a new video podcast, Initial Contact, distributed by Playmaker and sponsored by Polymarket. 

  • Yahoo Sports and Apple TV are collaborating on alt-casts for two MLS games and the first two innings of two MLB games. 

  • Nashville sports talk personality Jared Stillman had his credentials revoked by the Titans after a harsh line of questioning to quarterback Cam Ward. 

  • Jacques Doucet, who was the Montreal Expos’ French-language play-by-play broadcaster for 33 years, died at 86. 

 

Loud and Clear

The Ringer/YouTube

“Did not know about the proxy rules. Yeah, there’s some real rules with this stuff … and I learned my lesson.”

—Bill Simmons addressing the backlash to his proxy bet admission on Tuesday’s episode of The Bill Simmons Podcast. The Ringer founder confirmed FanDuel has since canceled the bets that his daughter’s boyfriend placed on his account in Massachusetts, while Simmons was in California.

 

Editors’ Picks

 
The 2026 NFL Season’s 13 Most Intriguing Media Personalities  

The 2026 NFL Season’s 13 Most Intriguing Media Personalities

By Michael McCarthy
Kirk Herbstreit and Tony Romo are among the notable names.
Netflix Secures Commercial Distribution for Expanded NFL Slate   

Netflix Secures Commercial Distribution for Expanded NFL Slate 

By Eric Fisher
The streaming giant’s full NFL slate will be shown in commercial establishments.
Kaepernick’s Legacy Lives On As NFL’s Anti-Racism Messaging Continues  

Kaepernick’s Legacy Lives On As NFL’s Anti-Racism Messaging Continues

By Michael McCarthy
It’s the seventh season the league has used such messaging.
EventsVideoGamesShop
 

Written by Ben Horney, Ryan Glasspiegel 

Edited by Ben Axelrod, Catherine Chen

 

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