Also: MLB's Olympics dilemma. ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌
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Front Office Sports - The Memo

Morning Edition

May 22, 2025

Justin Connolly is one of Disney’s longest tenured and most senior executives, and he just signed a multiyear contract. His intended move to YouTube carries significant implications for both companies.

Eric Fisher, Ben Horney, David Rumsey, and Colin Salao

Disney Sues YouTube for Poaching Exec With Deep ESPN Ties

Ron Chenoy-USA TODAY Sports

A seemingly straightforward executive move in sports media has snowballed into a lawsuit between two titans.

ESPN parent company Disney has sued YouTube TV and longtime Disney exec Justin Connolly over his move to the Google-owned streamer to a newly created role as global head of media and sports. 

Connolly spent nearly three decades with Disney, beginning as a financial analyst and ultimately becoming one of the company’s most senior executives, most recently as president of Disney Platform Distribution, overseeing direct-to-consumer services and content agreements across entertainment, studios, and sports, and working closely with ESPN chairman Jimmy Pitaro. 

Just last week, Connolly attended the press briefing in New York City at which ESPN  introduced its forthcoming direct-to-consumer service. 

Disney alleges that both YouTube and Connolly engaged in breach of contract, tortious interference of contractual relations, and unfair competition. The lawsuit, filed Wednesday in Los Angeles County Superior Court, claims Connolly signed a three-year employment agreement last November covering all of 2025-2027, with a one-time termination right becoming effective on March 1, 2027.

“YouTube committed intentional acts designed to induce Connolly to breach the employment agreement,” Disney said in the suit.

Amid the legal action, YouTube announced Connolly’s move internally on Thursday. A former Disney executive source tells FOS Connolly “knows all of the economics of ESPN—his information is priceless,” which explains why Disney is so up in arms over his exit.

If completed, the shift carries plenty of implications. Already the distributor of the residential version of NFL Sunday Ticket, YouTube’s fast-growing sports ambitions can also be seen in a recent deal to carry the league’s return to Brazil on Sept. 5 with the Chiefs and Chargers.

That game is poised to set a league streaming record, and the free distribution there is aimed at tapping into YouTube’s massive global audience of more than 2.5 billion monthly active users. Connolly is set to build on that by leading YouTube’s partnerships with media companies and sports leagues, including for YouTube TV, the country’s largest internet-based television service.

Meanwhile, Disney has its own set of major initiatives, including the debut later this year of the ESPN DTC service, as well as several other major distribution agreements to complete—most notably with YouTube. Connolly was set to lead that negotiation for Disney before the move to join YouTube. To that end, Disney said in the lawsuit that Connolly’s news arrived at a “critical time” in his tenure there.

“It would be extremely prejudicial to Disney for Connolly to breach the contract which he negotiated just a few months ago and switch teams when Disney is working on a new licensing deal with the company that is trying to poach him,” the suit reads in part.

Connolly was a finalist to succeed John Skipper as ESPN’s top executive in 2018, with that job ultimately going to Pitaro.

Representatives for Disney and YouTube did not immediately respond to FOS requests for comment Thursday evening.

MLB Weighs Olympic Participation After NFL Flag Football Approval

Rhona Wise-Imagn Images

This week’s approval of active NFL players competing in the 2028 Summer Olympics, one that still has plenty of unresolved layers, could be a mere prelude to an even more complex situation: the presence of MLB players. 

Baseball is back in the Olympic program for 2028 in Los Angeles, continuing a back-and-forth situation that saw the sport in the global competition 16 times between 1900 and 2008, then away from the Games for 13 years, returning for the pandemic-delayed 2021 Olympics in Tokyo, and then absent again last year in Paris. 

In addition to the wishes of local organizers, a core component of that variance has been the lack of competing MLB players. Historically, the league has been resistant to shutting down the schedule in a peak summer period to allow for that participation, instead often having minor-league players help comprise rosters. That dynamic also helped lead to the creation of the World Baseball Classic more than two decades ago, with that tournament owned and operated by the league and MLB Players Association and played in preseason windows. 

A different conversation, however, is now emerging between league commissioner Rob Manfred and LA28 president and chairman Casey Wasserman. In part because of the Summer Olympics returning to the U.S. after 32 years, the two have had an ongoing dialogue about ways that MLB players could be involved. 

Last year, Manfred said of 2028, “When you’re in L.A., it is an opportunity to think about,” a sentiment he has repeated at multiple points so far this year, though he has acknowledged the situation remains “complicated.” With the NFL formally on board for the flag football competition, LA28 is looking to reach a similar agreement with MLB.

“It’s the right thing for the sport of baseball, it’s the right thing for the players, and it’s certainly the right thing for the Olympics,” Wasserman told the Associated Press. “I think when things make sense for everybody, you can usually find a way to get things done.”

Additional Considerations

A further factor in the discussions is that Dodger Stadium, the home venue of the defending World Series champion Dodgers, will be the site of the 2028 Olympic baseball games. The Dodgers, led in part by Japanese phenom Shohei Ohtani, have been at the center of MLB’s accelerating globalization

Similar to the NFL, much of the baseball discussion has centered on health and safety protocols, and related insurance provisions should big-league players be involved. Because MLB will be in the heart of its 2028 season during the July 14–30 timing for the Olympics, further consideration involves managing the schedule and the impacts of a 17-day period that often generates some of baseball’s largest attendance and viewership of the year.

There is a parallel, however, in hockey. The NHL has often suspended its season to allow for Olympic participation, and a recent deal involving that league, the NHL Players’ Association, and IIHF calls for more such involvement. 

Indy 500 Sells Out for First Time Since 2016 Despite Series of Scandals

The Indianapolis Star

The Indianapolis 500 arrives this weekend with strong demand around the race locally, but controversy surrounding the sport’s owner.

The Indianapolis Motor Speedway is expecting attendance of 350,000 on Sunday after selling out its main grandstand for the first time since 2016, which was a unique circumstance as the 100th running of the iconic race.

That has led to IndyCar lifting its longstanding blackout of the local TV broadcast of the race for years when it does not sell out.

Fox is in its first season of a new media-rights deal with IndyCar as the sport’s lone U.S. broadcaster. Last year, the Indy 500 drew 5.34 million viewers on NBC, which was up 8% over the 2024 edition.

Prize money for Sunday’s race has not yet been revealed, but last year the Indy 500 shelled out a record $18.45 million, with winner Josef Newgarden taking home $4.2 million.

Penske Problems

Controversy continues to surround Roger Penske, who bought IndyCar and Indianapolis Motor Speedway in 2019 and still runs Team Penske, one of the most successful in the sport.

Penske fired his IndyCar team’s president, Tim Cindric, managing director Ron Ruzewski, and general manager Kyle Moyer on Wednesday after two Penske cars—Newgarden’s and Will Power’s—were found to have violated modification rules for Indy 500 qualifying last weekend. Newgarden and Power were sent to the back of the grid for Sunday’s race.

This came just over a year after Team Penske was involved in a cheating scandal early in the 2024 IndyCar season. Newgarden was retroactively disqualified from last year’s season-opening race, which he won, along with his teammate, Scott McLaughlin, for rule violations around the illegal use of an in-race technology.

Conversation Starters

  • Oscar Mayer will host the world’s first Wienie 500 at the Indy 500. Take a look.
  • Oklahoma City has declared Thursday as Shai Gilgeous-Alexander Day to honor the Thunder star for winning the 2025 NBA MVP award.
  • Gilgeous-Alexander bought his Thunder teammates Rolexes for helping him win the MVP award. Check it out.

Question of the Day

Should MLB suspend the 2028 season to allow players to be in the Los Angeles Olympics?

 Yes   No 

Thursday’s result: 48% of respondents think more than one NFL player per team should be allowed on the Olympic flag football roster.