Alex Bregman’s gamble pays off in huge way a year after leaving Astros

For much of last year, it looked like the Houston Astros were going to get the better end of their dance with Alex Bregman last offseason. Instead of returning to Houston on a 6-year deal worth $156M, the All-Star third baseman threw his loyalty to Houston to the side in favor of a three-year deal with the Boston Red Sox worth $120 million. After opting out of the deal after only the first year, Bregman's market appeared to be stalling before Scott Boras ultimately ensured his client got the last laugh over everyone.

The 31-year-old veteran has landed the long-term deal that he chose not to sign with the Astros (or Detroit Tigers) last year, inking a 5-year contract with the Chicago Cubs worth $175M. Bregman's deal with Chicago has no opt-out while also providing him with a full no-trade clause.

As much as Astros fans may not want to admit, their former franchise darling got the last laugh.

Taking into account what ultimately proved to be a one-year deal with the Red Sox, by the time his contract is up with the Cubs, Bregman will have earned $215 million since his departure from Houston. Of course, this revelation will do very little to discredit the notion that Bregman is nothing but a money chaser.

As true as that may be, the Astros missed Bregman during the closing months of the 2025 season. Isaac Paredes was sidelined with a hamstring injury that created an urgency for the Carlos Correa reunion at the deadline. Taking on Correa's bloated contract is one of the reasons why Houston has been walking a fine line financially with the moves they've made this winter.

Alex Bregman’s gamble just paid off in a big way — without the Astros

What makes things worse for Houston is that Paredes, the player who replaced Bregman at third base and earned an All-Star selection in his first year doing so, might be traded before Opening Day. The Astros' 2026 payroll outlook remains gridlocked, leaving almost no room for Dana Brown and Co. to operate without going over the luxury tax. Trading Paredes seems like the likeliest outcome, creating nearly $9M in space for Houston.

If Paredes is, in fact, traded before Opening Day, it's hard not to see how Bregman didn't get one over on his former team. He got the money, thanks to some creativity, and now has long-term security in Chicago. As they say, you can't win them all.