The Chicago Cubs haven’t made waves this offseason, as their acquisitions have, so far, amounted to mere ripples.
More News: Chicago Cubs: 3 under-the-radar free agents worth pursuing
The team’s current offseason talent haul consists of relievers Phil Maton and Hoby Milner, first baseman Tyler Austin, and the re-signing of Caleb Thielbar and Shota Imanaga.
If reports are to be trusted, however, the best is yet to come for the North Siders.
Target: 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
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A rumored top target is third baseman Alex Bregman, who the Cubs pursued last season before the veteran opted for the more flexible deal offered by the Boston Red Sox.
This year, Bregman is reportedly more focused on long-term stability and the Cubs seem much more open to going the long-term contract route. The more dogged pursuit could have something to do with an outgoing Kyle Tucker and a mass of veteran contracts ready to expire at the end of 2026 (Ian Happ, Nico Hoerner, Seiya Suzuki, Carson Kelly, Jameson Taillon, Matthew Boyd, Shota Imanaga).
Recent news has all been good when it comes to the Cubs’ pursuit of Bregman, with Chicago being named front runners as the Red Sox seem reluctant on an extended contract for the star, who will be 32 on opening day.
Now, though, another suitor has emerged– one with deep pockets and a recent wild aggression in the market.
The Toronto Blue Jays are now in the Bregman mix
Jul 21, 2025; Philadelphia, Pennsylvania, USA; Boston Red Sox third base Alex Bregman (2) against the Philadelphia Phillies at Citizens Bank Park. Mandatory Credit: Eric Hartline-Imagn Images
According to Ken Rosenthal of The Athletic, the Toronto Blue Jays are now firmly in the Bregman hunt, after a previous interest that just bordered on curiosity.
Per Rosenthal:
“Team officials have been in recent contact with Bregman’s agent, Scott Boras, according to sources briefed on the conversations. Ideally, the Jays want to add a left-handed hitter, but either the right-handed Bregman or Bichette would fit their defensive alignment better than Tucker or Cody Bellinger, both of whom bat left.”
The Blue Jays have made a splash this offseason, signing starting pitchers Dylan Cease and Cody Ponce, alongside reliever Tyler Rogers. They are also said to be heavily in the mix for Kyle Tucker and invested in possibly re-signing Bo Bichette.
If Toronto is, indeed, serious about Bregman, that would put the Cubs in a tough spot. Given the team’s history of frugality and their general conservative mindset, it seems unlikely that they would outbid a hungry Blue Jays team that got so close to a World Series win last season.
So, that’s the bad news.
But on the bright side…
MLB: Chicago Cubs at San Diego Padres
Apr 15, 2025; San Diego, California, USA; Chicago Cubs right fielder Kyle Tucker (30) hits a single during the fifth inning against the San Diego Padres at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images
A low-key positive of this development, however, is that the market for Kyle Tucker may experience a bit of a crash as previous suitors, like the Phillies and Yankees, have either bowed out or seem to have cooled on him.
Could that create an opening for the Cubs to explore a bid on their star, who many just assumed would be moving on to a contract wildly beyond the Cubs’ willingness to spend? Could a lowered Tucker asking price rekindle the Blue Jays’ interest and pull them away from chasing Bregman– something which, in turn, would make the Cubs once again the favorites to sign him?
Could the Cubs miss out on both Tucker and Bregman by being their usual frugal selves, banking on more budget-friendly in-house choices for third base and right field?
As is always the case, time will tell.
Chicago Cubs: 3 under-the-radar free agents worth pursuing
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