Chicago Cubs gut punch: Insider casts doubt on Cubs pursuit of Alex Bregman

The Chicago Cubs, last offseason, came in as late bidders for free agent third baseman Alex Bregman. At the time, it was widely reported that they were one of the favorites to land the former Houston Astro. Actually, everyone was led to believe that they had a pretty good chance to be the All-Star’s new team.

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When the dust settled, though, not only did Bregman sign with the Boston Red Sox, but it was later revealed that the Cubs weren’t finalists for his services at all.

The Cubs’ reported offer of four years for $115 million, with opt-outs after the 2026 and 2027 seasons, fell short of the Red Sox winning bid of $120 million for three years, with opt-outs after 2025 and 2026. It also fell short of the deals reportedly offered by the Detroit Tigers and Houston Astros.

Fans walked away from the 2025 Bregman chase with the feeling that, maybe, Chicago wasn’t chasing as aggressively as they had been led to believe.

Fast forward to 2026. Could everyone be in for the same kind of letdown and disillusionment?

Cubs fans headed for another Bregman letdown?

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With Bregman having exercised his opt-out clause with the Red Sox and once again peddling himself on the free agency market, reports have been hot and heavy regarding the Cubs and their pursuit of him. They’ve also, again, been named as favorites to sign him.

Mark Feinsand of MLB.com, however, recently let loose a tidbit of information that should get Cubs fans feeling like they’ve just taken a gut punch.

According to Feinsand’s sources, the Cubs may be in the mix of interested teams, but they’re not the hungriest to acquire him:

“Sources believe the Blue Jays and Diamondbacks may be the two most aggressive clubs in the hunt for Bregman, though a Red Sox reunion remains a possibility.”

The Red Sox, meanwhile, have said that the re-signing of Bregman is a “plan A,” according to sources talking to MassLive.com’s Chris Cotillo.

Reality check

Realistically, how far did anyone think this Bregman pursuit would go, anyway? The frugal Cubs ownership sees that they have a fine everyday third baseman in Matt Shaw on the roster right now making near league minimum.

The problem is that “fine” is not going to cut it if the goal is to field a better team in 2026.

Kyle Tucker will be gone and his absence from the lineup will be felt. It’s no coincidence that the Cubs’ prodigious 2025 offense cooled down considerably in the second half of the season as Tucker struggled with injury-related inconsistency. Tucker’s right field replacement, rookie Owen Caissie, is by no means a guaranteed hit.

Shaw was surprisingly good defensively at the hot corner, but came up short with the bat. The rookie was only able to reach his .226 batting average because of an August were he approached being a league-average hitter. Take away that month, and his average goes down to .223. Plus, there was the 2-for-17 postseason run that accentuated doubts and question marks about Shaw.

As things stand now, there is no backup to Shaw on the Cubs roster.

Then, moving away from the offense, there’s the fact that the Cubs have so far come up short in their pursuit of a high-end starting pitcher, losing bids for Dylan Cease and Japanese import Tatsuya Imai while seemingly keeping away from the rest of the deep end of the free agent talent pool.

No plan going forward?

Bringing Bregman aboard made infinite sense as Shaw could’ve then been packaged to a team okay with waiting on his progress in a deal for a quality starting pitcher. Or Shaw could’ve been kept as a utility man and as insurance for the possible loss of a free agent Nico Hoerner after next season.

Right now it looks like the Cubs may be facing the worst of both worlds– No Bregman and not enough trade capital to pull off a big trade for pitching.

As is always the case, though, time will tell what’s in store for the rest of the offseason.

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Source: https://www.chicitysports.com/chicago-cubs-alex-bregman-free-agent-matt-shaw