• Loading stock data...
Saturday, August 2, 2025
Tuned In returns to NYC on September 16. Hear from the biggest names in sports media. Click here to get your spot

Diamond Baseball Holdings Flexes Further With WooSox Deal

  • MiLB team holding company extends acquisition push with Boston’s top affiliate.
  • WooSox have been one of the top-performing teams in the minor leagues.
Alan Arsenault / USA TODAY NETWORK

One of the most underexposed but influential sports ownership entities is accelerating its already extensive efforts in Minor League Baseball. 

Diamond Baseball Holdings, which owns 26 teams spanning all levels of MiLB, is nearing a deal to acquire the Triple-A Worcester Red Sox, the top affiliate of the Boston Red Sox. The pact, estimated at about $70 million, would help reset the market for MiLB team sales, which typically go for low-to-mid eight figures.

The Worcester deal also represents one of the most prominent acquisitions in Diamond’s history. The WooSox are one of the top-drawing teams in Triple-A baseball and play in Polar Park, which opened in 2021 and is widely seen as one of MiLB’s best stadiums.

“It’s time to sell this team and to move on,” WooSox chairman and co-owner Larry Lucchino recently said on the “UnAnchored Boston” podcast.

Times Of Transition

The soon-to-be 27 teams in Diamond’s portfolio represent nearly a quarter of MiLB’s 120. But the company reportedly has ambitions to own perhaps 50 teams and has acquired four others in just the last two months. 

Diamond began operations in 2021, soon after MLB completed a historic overhaul of the affiliated minor leagues. It was originally owned by Endeavor — an arrangement that soon ran into issues, as the MLB Players Association claimed it presented a conflict of interest because Endeavor also owns talent agencies IMG and WME. 

Private equity giant Silver Lake, also the lead backer of Endeavor, ultimately purchased Diamond.

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Cubs Land 2027 MLB All-Star Game After Lengthy Pursuit

MLB will bring the Midsummer Classic to one of baseball’s cherished ballparks.
Carlos Correa
exclusive

Twins Moving Toward Selling Team After Deadline Teardown

Minnesota moved about 40% of its roster ahead of the trade deadline.
Jul 26, 2025; Minneapolis, Minnesota, USA; Minnesota Twins shortstop Carlos Correa (4) walks to the dugout after the ninth inning against the Washington Nationals at Target Field.

MLB’s Biggest Buyers in Frantic Deadline Weren’t Top Markets

Teams besides the Dodgers, Mets, and Yankees dominate MLB’s trade deadline.
Happy Gilmore 2

Is ‘Happy Gilmore 2’ Really About LIV vs. PGA Tour?

The movie’s main plotline may sound familiar to many golf fans.

Featured Today

Coco Gauff at New York Liberty

How the New York Liberty Became the Hottest Ticket in Town

Once banished to the burbs, the Libs are now Brooklyn’s marquee attraction.
Las Vegas sign
July 29, 2025

College Sports Embracing Vegas After Years of Cold Shoulder

The Big Ten became the latest newcomer to Sin City.
2000, Jupiter, FL, USA; FILE PHOTO; Montreal Expos pitcher Hideki Irabu in action on the mound against the New York Mets at Roger Dean Stadium during Spring Training
July 28, 2025

Dead Sports Franchises Are Alive and Well on Twitter

The Expos, Sonics, and Whalers have active social media accounts.
Limited Hype
July 27, 2025

Sneaker Reselling Was Once Easy Money. Success Is Now Complicated

Vendors need to evolve what they’re selling and how they do it.

Bengals Extend Stadium Lease After $350M in Public Funds for Renovation

The Bengals will stay in the 25-year-old stadium through at least 2036.
July 31, 2025

Ferrari Extends F1 Boss Weeks After Red Bull Fire Horner

Fred Vasseur joined Ferrari in 2023.
August 1, 2025

Commanders Seal Stadium Deal As D.C. Approves $1.1B in Funding

The NFL team’s return to its prior home receives key political support.
Sponsored

Game On: Portfolio Players Stories, Brought to You by E*TRADE from Morgan Stanley

Dealmaker Jeffrey Kaplan maps the evolution of sports as an asset class
July 30, 2025

Mayor Calls Commanders RFK Stadium Deal ‘a BFD’ for D.C.’s Future

The NFL team makes a series of additional commitments.
July 30, 2025

Trey Hendrickson Ends $450K Holdout Without New Bengals Deal

The defensive end is seeking a raise on his $16 million 2025 salary.
July 29, 2025

Wrexham’s Ambition Replaces Fan Favorites With Pricey Additions

Wrexham has already added six new players.
July 29, 2025

Mario Lemieux Trying to Reacquire Penguins 4 Years After Selling

The former NHL great looks to return to team ownership.