Also: MLB’s 2026 schedule is out, but changes are coming. ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌
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Front Office Sports - The Memo

Afternoon Edition

August 26, 2025

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Donald Trump Jr. is making waves in the prediction-market world, investing eight figures in Polymarket while serving as an advisor to rival Kalshi. His move raises eyebrows amid Polymarket’s push to reenter the U.S. market.

Ben Horney, Eric Fisher, and David Rumsey

Kalshi Advisor Donald Trump Jr. Joins Rival Polymarket Board

Arizona Republic

Donald Trump Jr. is investing in prediction-markets exchange Polymarket through his venture capital firm, a curious move that could create the appearance of a conflict of interest since the president’s son is separately a “strategic advisor” for rival Kalshi.

As part of the undisclosed investment from Palm Beach, Fla.–based 1789 Capital, Trump Jr. will also join Polymarket’s advisory board, according to a statement. The firm is injecting “double-digit millions of dollars” into Polymarket, Axios reported.

The news comes as Polymarket has been making a push to reenter the U.S. market. It has been banned from operating in the country as part of a 2022 settlement with the Biden Administration.

Other recent moves signaling the imminent reentry into the U.S. include the company’s June agreement to become the official prediction markets partner for X, the announcement a few weeks later by Polymarket founder Shayne Coplan that the company had “been cleared of any wrongdoing” in a federal investigation, and its July acquisition of QCX, a small derivatives exchange that was recently licensed by the Commodity Futures Trading Commission. Coplan was the subject of an FBI raid last year, with agents taking electronics from his apartment. In his words, they were “looking for anything that could imply foul play.”

Additionally, the company has been running ads suggesting it will be available in the U.S. any day now, and reportedly its reentry could take place within the next two weeks.

Trump Jr., who has been a strategic advisor to Kalshi since January, said in Tuesday’s press release that “the U.S. needs to access this important platform.”

Kalshi declined to comment. When the company announced it was bringing him on, Kalshi said Trump Jr.’s “bold business mindset and deep understanding of market dynamics perfectly align with Kalshi’s mission to redefine how America engages with information.”

Trump Jr. being involved with both Polymarket and Kalshi is odd, although it’s not clear whether this rises to the level of a legal or regulatory conflict of interest. Trump Jr.’s role with Kalshi is a paid position, according to Axios

Polymarket and Kalshi are rivals in the nascent, but growing, area of prediction markets. 

Both companies have engaged in outlandish behavior, including on social media and through some of the event contracts they offer. They also both recently raised millions of dollars; in June, one day after Bloomberg reported Peter Thiel’s Founders Fund led a more than $200 million investment in Polymarket at a $1 billion valuation, Kalshi scored $185 million in a funding round led by crypto-focused venture capital firm Paradigm.

Prediction-market platforms like Kalshi and Polymarket give users the ability to trade money on outcomes of events, such as whether there will be a recession this year or whether it will rain in New York City today. As of this year, both companies offer sports event contracts, which allow users to trade on matters like which team will win a given game. 

The sports offerings have drawn the ire of state regulators, which have jurisdiction over sports gambling, and the NFL has warned that their offerings are identical to traditional sports betting—but with less oversight and regulation.

Representatives for the CFTC and 1789 Capital did not immediately respond to requests for comment. 

MLB Unveils 2026 Schedule As Big Changes Loom Soon After

Allan Henry-Imagn Images

The 2026 Major League Baseball schedule is now out. It will feature many of the same elements as in recent years, but even bigger changes are likely coming.

Again using the balanced format in use since 2023, the league released Tuesday afternoon its master schedule for next year. Among the core elements of the 2026 slate:

  • A return to Iowa for the revival of the Field of Dreams Game, this time involving the Phillies and Twins. This will be the latest iteration of MLB’s ongoing push to stage special-event domestic games in the regular season. This event, however, was not part of Tuesday’s schedule release as the league and local officials finalize logistics for the planned game.
  • A planned resumption of Rays home games at hurricane-damaged Tropicana Field. The schedule includes a return to the venue on April 6 for the home opener after a nine-game road trip to start the season. This year, the Rays have been playing home games at George M. Steinbrenner Field, the spring training home of the Yankees, while repair work continues. That club’s long-term facility future is still unknown, but it is expected to get a new majority owner soon.
  • A continuation of the interim stay of the A’s in Sacramento while a new ballpark is built in Las Vegas. The A’s still are operating without a geographic signifier. The team, however, has two home series in June slated for Las Vegas Ballpark, the home of its top minor-league affiliate, serving as something of a preview of its forthcoming home market. 
  • A repeat of the Rivalry Weekend promotion that sparked a big attendance lift this past spring. 
  • A creation of several nontraditional off days in markets such as Philadelphia, Kansas City, Seattle, and Arlington to accommodate FIFA men’s World Cup matches being played at nearby football stadiums.
  • A matchup between the Yankees and Mets on Sept. 11 to recognize the 25th anniversary of the terrorist attacks in the city. 

Next year’s schedule will also be preceded by the return of the World Baseball Classic, which is slated for March 6–17. MLB recently signed a rights deal with Netflix in Japan for that tournament. 

The season itself will start with a single game on March 25 between the Yankees and Giants in San Francisco, marking the league’s earliest domestic start. That will be followed by a full Opening Day the next day. The 2026 All-Star Game is set for July 14 in Philadelphia, while the final day of the regular season will be Sept. 27. A series of planned international games are either still being finalized or are no longer happening, and Tuesday’s release contained no such games.

Prelude to Larger Shifts

While next year’s schedule follows much of the same format as recent years, bigger changes are on the way, and soon. MLB is in the midst of completing a set of national media-rights deals for the 2026–28 seasons to reallocate rights previously held by ESPN. The Disney-owned ESPN is set to remain involved with the league, albeit in a significantly restructured fashion. 

Meanwhile, MLB commissioner Rob Manfred is talking more openly about a large-scale realignment that would likely end the traditional American and National leagues and introduce an entirely new scheduling format. Many of those elements, however, will need to be collectively bargained with the MLB Players Association, and would arrive in concert with a league expansion to 32 teams. 

Overwhelmed—Again

The Tuesday afternoon release of next year’s MLB schedule, however, arrived within minutes of Taylor Swift’s online announcement that she is engaged to Chiefs tight end Travis Kelce. 

“Thanks a lot, Taylor Swift,” the Guardians said in a social media post with its 2026 slate. “Now no one cares that next year’s schedule is out.”

The Marlins similarly leaned in to the engagement news, saying, “She got a rock, we got the Rockies on opening day.”

NFL Roster Cut Deadline Passes After Backup QB Carousel

Vincent Carchietta-USA TODAY Sports

NFL clubs made their final training camp cuts Tuesday as the 53-man roster deadline passed at 4 p.m. ET following nearly 1,200 players being released since the weekend’s preseason finales.

Although there weren’t any franchise-altering moves, there was plenty of movement at the league’s most important position. Trades, releases, and new signings created somewhat of a backup quarterback carousel in recent days. Most teams have three, four, and five QBs during the preseason when rosters are at 90 players, but mostly carry only two on the active roster during the season.

Among the biggest moves was the Browns trading Kenny Pickett to the Raiders for a fifth-round pick in the 2026 NFL Draft. Cleveland also released Tyler Huntley, as the team trimmed its packed QB room that still includes presumptive starter Joe Flacco, rookies Dillon Gabriel and Shedeur Sanders, and the injured Deshaun Watson.

The Vikings traded Sam Howell to the Eagles and signed Carson Wentz to serve as first-year starter J.J. McCarthy’s primary backup. 

In a surprise move, the Buccaneers released fifth-year pro Kyle Trask in favor of Teddy Bridgewater, 32, who just came out of retirement to sign with Tampa Bay earlier this month. 

Meanwhile, the Giants released Tommy DeVito, who gained fame as an undrafted rookie in 2023, as New York is set to move forward with veterans Russell Wilson and Jameis Winston alongside rookie first-round pick Jaxson Dart. 

The Cousins Dilemma

The Falcons released two QBs, Ben DiNucci and Easton Stick, as Kirk Cousins, who has a $40 million salary-cap hit this season, looks set to back up second-year signal-caller Michael Penix Jr.

Cousins skipped some offseason team practices after asking for a trade, but he has been a full participant in training camp. The 37-year-old is entering the second season of a four-year, $180 million deal he signed as a free agent last March.

FRONT OFFICE SPORTS TODAY

Dave Portnoy Banned From Ohio State?

FOS illustration

Dave Portnoy will not be allowed inside the Horseshoe during Fox’s Big Noon Kickoff for Texas vs. Ohio State this weekend, but nobody wants to take responsibility for the ban. Ohio State says it was Fox’s decision, Portnoy says it was the Buckeyes’ choice. FOS media reporter Ryan Glasspiegel broke this story and explains what it means for Portnoy and Barstool Sports during this upcoming CFB season.

Plus, the WNBA seems to be headed for a lockout, with CBA talks stalling ahead of the Oct. 31 deadline. FOS women’s sports reporter Annie Costabile reports that a work stoppage is likely but not certain. She joins Baker Machado and Renee Washington to explain where things stand.

Also, Darrelle Revis calls out Jerry Jones for violating the CBA, Caitlin Clark drops a new logo, and “Babe Ruth” is getting sued.

Watch the full episode here.

STATUS REPORT

Three Up, One Down

Robert Deutsch-Imagn Images

NFL Swifties Chiefs tight end Travis Kelce on Tuesday announced his engagement to Taylor Swift, who has helped the league gain new fans since she began dating the four-time first-team All-Pro in 2023. Earlier this month, the Kelce brothers’ podcast, New Heights, reached 1.3 million live viewers during Swift’s first appearance on the show. The NFL congratulated Kelce and Swift from its official social media accounts.

Rahsul Faison The South Carolina running back has been granted a seventh year of eligibility to play for the Gamecocks this season. Faison, 25, transferred from Utah State, where he played the previous two seasons. His college career has also included stops at Snow College in Utah, Lackawanna College in Pennsylvania, and Marshall. His decision to seek a seventh year came after Vanderbilt quarterback Diego Pavia’s successful lawsuit against the NCAA.

Non-conference scheduling ⬇ Alabama and West Virginia have canceled their home-and-home series originally set for the 2026 and 2027 college football seasons as a result of the SEC implementing a nine-game conference schedule. Alabama is replacing WVU with East Carolina in 2026.

Chase Daniel The retired NFL quarterback is among the new additions to ESPN’s lineup of college football announcers for the upcoming season, which was officially announced Monday. Daniel, who was most recently a cohost of FS1’s studio show The Facility, will be a game analyst alongside play-by-play man Clay Matvick. Daniel will also be an NFL studio analyst for ESPN.

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