Cubs to sign Alex Bregman to five-year, $175 million deal

Last week on this blog, we said the Cubs' acquisition of starting pitcher Edward Cabrera wouldn't mean much if they didn't go all in to sign one of the big four remaining free agent batters.

I suggested the North Siders pursue Bo Bichette. While they did not do that, the Cubs are signing one of the four players on that list, as third baseman Alex Bregman has reportedly agreed to a five-year deal worth $175 million. 

A three-time All-Star and two-time World Series winner, Bregman was on the free agent market a year ago at this time, but he wasn't finding any offers to his liking. He was coming off a down season in 2024 -- a career-worst .315 OBP.

So, he took a two-year contract with the Boston Red Sox, with a one-year opt-out. In the hitter-friendly environment at Fenway Park, Bregman bounced back in 2025. He batted .273/.360/.462 with 18 homers and 62 RBIs, even though injuries limited him to 114 games. His OPS+ was 128, which ranks as his fourth-best season in his 10-year career. 

Bregman exercised his opt-out, re-entered free agency, and the bet has paid off in this deal with the Cubs. 

A word about opt-outs, because I've seen some Cubs fans on X suggesting the team reunite with outfielder Kyle Tucker by offering him a high-AAV deal with an opt-out.

If a player is going to take a contract with an opt-out clause, it behooves that player to sign with a team that plays its home games in a hitters' ballpark, which is what Bregman did with Boston last season. 

Perhaps once upon a time Wrigley Field was such a place. But since they put up those scoreboards behind the bleachers there, the wind currents have shifted, and Wrigley is a more pitcher-friendly place.

It's hard to say, "I'll sign with the Cubs, put up big numbers, then opt out after one year and get bigger money," because there are easier places to put up big numbers than in Chicago.

To entice a big free agent bat, the Cubs were going to need to go long term. That's what they've done with Bregman, and it's a big swing they needed to take.

This is the type of move that big market teams should be doing.