Will Cubs regret losing out on Alex Bregman

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Alex Bregman playing for the Houston Astros

In February, the Cubs were linked to All-Star third baseman Alex Bregman with many expecting him to land in Chicago. Instead, he would end up signing a 3-year $120 million with the Boston Red Sox. Despite showing major interest, the Cubs were unable to acquire his services.

Alex Bregman has been one of the best third basemen of this generation. He is a 2x All-Star, 2x World Series champ, a silver slugger, and a Gold Glove winner. He has accumulated 39.6 bWAR in his nine-year career. His career slash line of .260/.315/.453 with a .848 OPS is superb. Add this to this consistent gold glove-caliber defense at the hot corner and it’s easy to see why he was so coveted this offseason.

The Red Sox had a much better offer

Despite third base being a major question mark this season, the Cubs were unable to reunite him with former Astros teammates Kyle Tucker and Ryan Pressley. The Cubs and Alex Bregman had mutual interest as many insiders speculated the 30-year-old veteran would wind up in Chicago when things were said and done.

However, Bostom was able to pry him away from the Cub’s hands. It was initially reported that the Red Sox offered a much more lucrative deal. And now we finally know exactly how much. According to MLB insider Jon Heyman “The Cubs and Red Sox apparently were Bregman’s preferred destinations, but Chicago’s best offer of $115 million over four years couldn’t touch winning Boston’s $120M over three, even with significant deferrals in the Red Sox deal.”

Understandably, Bregman would prefer the higher AAV, about $12 million more per season, and $5 million more overall. While the Cub’s offer was more years, they paid less both in total and per year. From a numbers standpoint, the Red Sox’s offer blew the Cub’s offer out of the water.

Should the Cubs have made it work?

So why didn’t the Cubs cough up the cash to bring Bregman to Wrigley? On one hand, you could argue the Cubs should spare no expense to improve a position that was dreadful for them last season. Last season Cub’s third basemen batted a combined .204 with a laughable .622 OPS and 79 OPS+.

So what gives? Is this yet another instance of Jed Hoyer and Tom Ricketts being cheap? Well, there may have been a good reason for the Cubs to balk at that $40 million AAV price for Bregman. His name is Matt Shaw.

Big faith in Matt Shaw

Matt Shaw is the Cub’s top prospect and is a future star in the making. He is the Cub’s current answer to the question of how they will fix their third base spot long-term. Shaw has the most potential of any third baseman the Cubs have rostered since Kris Bryant debuted in 2015. The twenty-three-year-old has cruised through the minors and has earned his opportunity to make his MLB Debut in Tokyo this week.

It is perfectly reasonable to assume the Cubs didn’t want to allocate that many financial resources to Bregamn, when they may already have the answer in-house. Sure, Shaw could have moved to second to make way for Bregman at third, but then what would happen to Nico Hoerner? Hoerner is far too valuable to be a bench player, and given his recent injury his trade value is likely tainted. Would the Cubs sell low on their former gold glover to make way for an incoming prospect?

While the roster shuffle could have worked (maybe) is it worth the trouble for a declining expensive 30-year-old? I don’t think this is a case of the Cubs being cheap. I believe it is a positive sign of how much they believe in Matt Shaw at third.

Michael DeFrancisco Michael DeFrancisco is a writer and contributor for covering the MLB for Heavy Sports. He started working at Heavy in 2025 and has experince covering Chicago Sports. More about Michael DeFrancisco