The Chicago Cubs had a bit of a confusing offseason this year.
They added plenty of pieces and filled holes in the roster after declaring themselves “all in” on making postseason play this coming season.
On the other hand, when facing scenarios where they could actually prove themselves to truly be “all in,” they demurred and fell back on the conservative mindset that many have argued has capped their ability to compete consistently at the highest level.
Acquiring elite-level right fielder Kyle Tucker from the Houston Astros was an aggressive move by Cubs president of baseball operations Jed Hoyer, but one that required no extra spending by the owning Ricketts family .
Similarly, bringing in the Astros’ ex-closer Ryan Pressly in a separate trade seemed to be an aggression-on-a-budget move from a team not entirely “all in.”
Both Tucker and Pressly are coming to the Cubs in the last year of their contract, with the general consensus being that they won’t be extended.
The Chicago Cubs’ Mixed Signals
The mixed signals coming from those at the highest levels of the organization have been a frustrating thing to watch for fans. It’s especially frustrating when the Cubs stand as one of the most lucrative franchises in all of sports and the fourth most valuable baseball franchise– after the New York Yankees, Los Angeles Dodgers, and Boston Red Sox– with an estimated worth of $5.31 billion.
Indicative of this off-putting dynamic were the team’s two whiffs on high-end free agent acquisitions this year– closer Tanner Scott and third baseman Alex Bregman. In both cases, the Cubs reportedly lost out on their intended targets over a stubborn unwillingness to add a bit extra to their offers via deferred money.
The Whiff On Alex Bregman
Bradford Doolittle of ESPN.com recently wrote up the Bregman fail as the Cubs’ most prodigious miss this offseason in a piece titled “MLB 2025: Why your team didn’t do what you wanted this winter.”
Per Doolittle:
“Why the heck didn’t the Cubs get Alex Bregman?
Clearly, they didn’t offer Bregman a good enough contract. Simple enough. The question isn’t really about Bregman but more why the Cubs seem so unwilling to get aggressive with their payroll. There’s a big difference between aggressive and reckless, and you can’t really encourage the latter. Also, teams are going to have periods of payroll expansion and retrenchment, and it’s only through a longer timeline that you can see whether or not a club is really making full use of its spending capacity. At this point, it’s really hard to say the Cubs are doing that. They are, after all, a top-five revenue team working on a fourth straight year of being a second-tier spender.
…For now, the Cubs should be fine in a soft division that is there for the taking. The bigger question might be written here a year from now: Why the heck didn’t the Cubs keep Kyle Tucker for more than one season?”
As The Dust Settles…
Cubs’ top prospect Matt Shaw will get every opportunity to win the third base gig in the absence of Bregman. But there’s no guarantee that the 23-year-old is ready for the big leagues yet, especially with just two years of pro ball under his belt and just 88 total games, between the minors and college, at third base.
The established veteran Bregman would’ve been an addition more in line with the needs of a team pushing for deep postseason play in the present tense, but things didn’t end up working that way.
Now, the Cubs and their fans will just have to hope for the best after the team’s “all in,” but not “all in” offseason.
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