Sunday, July 19, 2026

Red Sox Return to Big Spending With $120M Alex Bregman Deal

The Red Sox for years were an economic force in MLB. A deal with Alex Bregman partly revives that spirit.

Troy Taormina-Imagn Images

Are the Red Sox again acting like a big-market MLB club that once defined the ownership era led by John Henry? A $120 million free-agent deal for infielder Alex Bregman suggests that may be the case. 

Bregman, previously a two-time champion with the Astros, agreed to a three-year contract with Boston late Wednesday, according to multiple reports, after becoming the most notable free agent left in a chilled player market. The pact, though it contains opt-outs after each of the first two years and some deferred money, features a $40 million annual salary that ties Bregman for fourth highest among all MLB players

More broadly, the agreement also heralds a more aggressive thinking by the Red Sox. The club’s luxury tax payroll is now nearly $237 million, the seventh highest in the league, after ranking 12th last year and in 2023. The Red Sox are now poised to play the 2025 season with the highest payroll in franchise history, and ultimately end up over the $241 million luxury tax threshold for this year. 

Back to the Past

Such activity is a marked turn for a team that became notably less aggressive in its spending over the past five years and saw stars such as Mookie Betts and Xander Bogaerts leave either by trade or free agency after failing to come to terms on new contracts. 

That dynamic, in turn, has made for one of the most complex team-fan relationships of any MLB franchise. On one hand, the 23-year Henry era has included the end of the famed Red Sox championship curse, three additional titles, the highly regarded restoration of Fenway Park, and more than $120 million in charitable foundation grants—a combined legacy that any team would be proud to boast.

More recently, however, the loss of icons such as Betts, reduced payrolls, and three straight non-playoff seasons have introduced a whole new level of unease among Red Sox fans. 

The addition of Bregman, however, could certainly help ease that angst, and even before the deal was formally announced, local media was cheering the development. 

“This is a strong move by the Red Sox,” wrote venerable Boston Globe columnist Dan Shaughnessy. “They have finally rewarded their fans. Just like the old days.”

In December, the Red Sox also traded for pitcher Garrett Crochet in a large-scale deal with the White Sox and added fellow hurlers Walker Buehler and Aroldis Chapman in free agency.

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

Jul 5, 2026; Chicago, Illinois, USA; Chicago Cubs second baseman Nico Hoerner (2) slides into score against the St. Louis Cardinals during the sixth inning at Wrigley Field.

Pending Labor Talks, MLB Is Set for Earliest Opening Day in 2027

Labor woes cloud the consideration of next year’s slate.
Jul 13, 2026; Philadelphia, PA, USA; Tampa Bay Rays third baseman Junior Caminero (13) bats in the second round of the All Star-Home Run Derby at Citizens Bank Park.

Home Run Derby Ratings Drop 7% on Netflix

The event’s pivot to streaming results in a slightly lower average audience.
Jul 14, 2026; Philadelphia, Pennsylvania, USA; General view of fireworks over Citizens Bank Park during the fourth inning of the All-Star Game.

MLB All-Star Game Ratings Get a Boost From World Cup

The midseason showcase’s audience rises with a World Cup lead-in.

MLB’s Stretch Run Will Be Defined By Labor, Stadiums, and Stars

The trade deadline and contending low-budget teams also loom large. 
podcast thumbnail mobile
Front Office Sports Today

A Conversation with Nate Burleson on Russell Wilson at CBS, Travis Kelce’s Media Future, and Seahawks $9.6B Sale

0:00

Featured Today

Tom's Watch Bar

Sports Bars Are Cashing In From Summer of Soccer

The World Cup has brought a windfall to America’s biggest sports bars.
Jun 16, 2026; East Rutherford, New Jersey, USA; France forward Michael Olise (11) controls the ball against Senegal during a Group I match of the 2026 FIFA World Cup at New York New Jersey Stadium
July 16, 2026

Where World Cup Stars Go to Customize Their Cleats

The world’s best players turn to a Scottish craftsman for perfect cleats.
July 10, 2026

What the World Cup Means to Erling Haaland’s Tiny Hometown

The tournament’s breakout star is from a rural Norwegian town.
July 10, 2026

Why So Many Media Outlets Are Rushing Into Sports

Sports coverage has ballooned in every corner of media.
Pillow Fight Championship
July 8, 2026

How Obscure Sports Get Mainstream TV Deals

For niche sports, getting on TV often matters more than getting paid.

WNBA Union Blasts Chicago Sky For Yet Another Facility Delay

The facility has been delayed multiple times since being announced in 2024.
July 16, 2026

Mark Cuban Gearing Up for Lawsuit Over New Mavs Arena

Cuban seeks to prove Patrick Dumont unlawfully cut him out of opportunities.
Mar 8, 2026; Milwaukee, Wisconsin, USA; Milwaukee Bucks forward Gary Trent Jr. (5) drives for the basket against Orlando Magic guard Jevon Carter (2) in the first quarter at Fiserv Forum.
July 16, 2026

NBA Investigating Gary Trent Jr.’s New Bucks Contract

Trent agreed to a four-year, $64 million deal on July 11.
Sponsored

Clase Azul Tequila Founder’s Soccer Ownership

Arturo Lomeli talks about managing a tequila brand and two soccer clubs.
Jerry Colangelo sits courtside as the GCU Lopes play the Oklahoma State Cowboys at Mortgage Matchup Center on Dec. 6, 2025, in Phoenix, Arizona.
First at FOS
July 15, 2026

Las Vegas Jacks Have Been in the Works for Over a Year

The group paid $2,200 in fees to apply for the two trademarks.
July 12, 2026

Seahawks Set NFL Record With $9.612B Sale to Khosla

Vinod Khosla’s wife will “serve as the controlling owner.”
Jun 20, 2026; Raleigh, North Carolina, USA; Carolina Hurricanes left wing William Carrier (28) and defenseman K'andre Miller (19) walk out with the Stanley Cup trophy during the Stanley Cup championship parade and rally at Raleigh.
July 10, 2026

Dundon Faces Backlash for Engraving Kids’ Names on Stanley Cup

All five names of the owner’s children are on the Stanley Cup.
Feb 8, 2026; Santa Clara, CA, USA; Seattle Seahawks wide receiver Cooper Kupp (10) catches a pass against New England Patriots cornerback Marcus Jones (25) in the first half in Super Bowl LX at Levi's Stadium.
July 9, 2026

Two Bidders Pull Ahead in Seahawks Sale Process

One of the two groups includes at least one former Seahawks player.