Inside The Cubs

Alex Bregman’s Wife Reagan Toasts $175 Million Cubs Signing With 1 Word Message

Alex Bregman celebrated his massive contract with the Chicago Cubs in fitting fashion.
Aug 27, 2025; Baltimore, Maryland, USA;  Boston Red Sox third baseman Alex Bregman (2) gestures on the field before the game between the Baltimore Orioles and the Boston Red Sox at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images
Aug 27, 2025; Baltimore, Maryland, USA; Boston Red Sox third baseman Alex Bregman (2) gestures on the field before the game between the Baltimore Orioles and the Boston Red Sox at Oriole Park at Camden Yards. Mandatory Credit: James A. Pittman-Imagn Images | James A. Pittman-Imagn Images

There has been a lot of pressure on the Chicago Cubs to make a major splash in free agency this offseason, given that they're losing Kyle Tucker.

And the Cubs made that splash on January 10, as news has broken that they signed Alex Bregman to a five-year, $175 million contract, according to ESPN MLB insider Jeff Passan.

This is now the third biggest contract in Cubs history, only falling $2 million short of the seven-year, $177 million deal that Dansby Swanson signed a few offseasons ago and $9 million less than the deal Jason Heyward got in December of 2015.

There have been rumblings that the Cubs were very interested in signing Bregman for months now. However, some Cubs fans were skeptical that the team would ultimately make it happen. This is because Chicago has been notoriously hesitant to hand out massive contracts in free agency, and Bregman didn't seem like a great fit for the team on paper, given that they have Matt Shaw at third base and Nico Hoerner manning second.

However, Jed Hoyer clearly wanted the three-time MLB All-Star and two-time World Series champion who hit .273 with an .822 OPS with the Red Sox in 2025 on his roster. And he ultimately got the deal done.

Boston Red Sox third baseman Alex Bregman (2) throws on September 25, 2025
Sep 25, 2025; Toronto, Ontario, CAN; Boston Red Sox third baseman Alex Bregman (2) throws out Toronto Blue Jays catcher Tyler Heineman (not pictured) at first base during the third inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images | John E. Sokolowski-Imagn Images

Alex Bregman celebrates Cubs signing with wife Reagan

It didn't take Bregman and his wife, Reagan, like to celebrate this massive contract, as she made a January 10 post to her Instagram story in the wake of this news breaking. She and Bregman can be seen toasting what appears to be margaritas at a restaurant.

"Proud ❤️," the story was captioned.

Regan Bregman's January 10 Instagram story.
Regan Bregman's January 10 Instagram story. | Instagram/@reaganelizabeth

It will be fascinating to see what the Cubs do with the rest of their roster in the wake of bringing Bregman on board. The most logical outcome would be for them to try and trade Nico Hoerner, even though that would be a tough pill for Cubs fans and the franchise as a whole to swallow.

But the team could get a good haul in return for Hoerner. What's for sure is that the Cubs have had a very successful past few days, as they're still coming off the trade they made for former Miami Marlins pitcher Edward Cabrera.

It's hard to imagine that Chicago will make many more big moves this winter after these two huge splashes in the past couple of days. Like Regan Bregman, Cubs fans have got to be feeling proud about their team right now.

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Grant Young
GRANT YOUNG

Grant Young is a Staff Writer for On SI’s Chicago Cubs, New York Mets, Boxing, Indiana Fever, and Women’s Fastbreak sites. Before joining SI in 2024, he wrote for various boxing and sports verticals such as FanBuzz and NY Fights. Young has a bachelor’s degree in marketing and a master’s degree in creative writing with an emphasis on sports nonfiction from the University of San Francisco, where he played five seasons of Division 1 baseball. He fought Muay Thai professionally in Thailand in 2023, loves a good essay, and is driven crazy trying to handle a pitpull puppy named Aura. Young lives in San Diego and was raised in the San Francisco Bay Area.