Chicago Cubs have been waiting for their team to make a big free-agent splash for years now, and while the Cubs swung a trade to acquire Kyle Tucker last winter, just about everyone assumed Tucker would be a one-and-done in Chicago.
It’s looking more and more like Tucker will be signing elsewhere, as the Cubs have not even been floated as a potential destination for the four-time All-Star. However, Chicago has been in on one of the other top free agents on the market: third baseman Alex Bregman.
The Cubs currently have Matt Shaw manning the hot corner, but they would almost certainly move him to make room for Bregman. There has also been speculation that the Cubbies could trade second baseman Nico Hoerner, which may lead to Chicago jettisoning Hoerner, putting Shaw at second and then slotting Bregman over at third.
But will the Cubs actually be able to beat out the Boston Red Sox, with whom Bregman spent 2025?
It initially looked like the Red Sox were the sure-fire favorites to retain Bregman, but things may be changing.
Are the Chicago Cubs now the favorites to land Alex Bregman?
Jul 28, 2025; Minneapolis, Minnesota, USA; Boston Red Sox third baseman Alex Bregman (2) runs the bases and watches his three run home run against the Minnesota Twins in the fifth inning at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images
Much like Chicago, Boston has not been a free-spending franchise in recent years in spite of playing in such a large market. And much like Cubs fans, Red Sox fans have become increasingly frustrated with the lack of activity.
Well, Jared Carrabis of Underdog has revealed some intel on the Bregman situation, and he doesn’t seem to feel that the 31-year-old will be returning to Beantown.
“I don’t feel super great about Bregman coming back, but these things are always subject to change,” Carrabis posted on X. “[Xander] Bogaerts was pretty much a done deal to return until the Padres swooped in with a crazy offer. These situations are fluid. But, yeah. Doesn’t sound promising at the moment.”
The Cubs and Red Sox have long been viewed as the two top potential landing spots for Bregman, although the Arizona Diamondbacks have apparently thrown their hats into the ring, as well.
However, Bregman to Arizona just doesn’t seem all that probable, especially considering that there have been strong rumors that the Diamondbacks are trying to trade Ketel Marte. Moving a veteran in Marte and then turning around and signing an aging Bregman would send weird signals.
Chicago, on the other hand, is trying to win now, and if the Cubs do ultimately lose Tucker in free agency, landing Bregman would be a nice consolation prize.
Perhaps the Cubbies really are the favorites to bag the three-time All-Star, who slashed .273/.360/.462 with 18 home runs and 62 RBI in 114 games this past season.
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