For the most part, introducing a newly-signed star free agent is simply about the celebration. It’s a definitive moment – completely with the new jersey and cap – to enjoy that this guy is truly part of the Chicago Cubs. So it was today with Alex Bregman, and I’m ready to contemplate all the permutations of what the 2026 Cubs could and will be with Bregman in the fold.
That said, if you’re lucky, you also get a little bit of insight from these things. Maybe about the player. Maybe about the organization. Maybe both.
Sure enough, there were two such things that really stood out to me from today’s press conference. One about Bregman. One about the organization.
Alex Bregman Really Walks the Walk
The vast majority of star players, upon signing a big deal, will be described as being a great teammate, a good leader, and so on and so forth. Maybe they are loud about it and in your face. Maybe they lead by example. I’m not saying it’s always fluff, but some variation of it is pretty common.
That said, this Cubs front office pretty clearly does have a preference for targeting baseball obsessives who bring that energy into the clubhouse with them. Dansby Swanson is definitely like that. Jameson Taillon is definitely like that.
Alex Bregman, it turns out, is DEFINITELY like that:
Jed Hoyer says Alex Bregman asked for a scouting reports on all his teammates, asked for a meeting with all the minor-league staff in Arizona on hitting philosophies & reached out to his new teammates. pic.twitter.com/lVFyWtvd5x
— Cubs Zone (@CubsZone) January 15, 2026Joining a new organization, and within two days, Bregman wants to know as much as he can not only about his new teammates, but ALSO wanted to meet with the minor league staff in Arizona. Why? Because Bregman wanted to make sure he fully understood the organization’s hitting philosophy with those young players. Again, why? Because he wants to be able to talk to them about the right things when he interacts with them.
This is a guy on track to earn more than $300 million in his career, has multiple championships, and was just courted to be the centerpiece of the organization’s next steps. And he’s out there immediately wanting to serve as a part-time player development coach.
We heard about Alex Bregman’s relationship with his teammates before, and how he helped so many of them improve throughout their career, but it still catches you a little flat-footed to hear exactly what that looks like. I hope very much that Bregman performs on the field to directly help the Cubs win games, but you can already have some confidence that he’s going to be helping a whole lot of young players get better in ways that may not show up on his personal stat sheet.
Reconsidering Contract Deferrals
By the very nature of the Alex Bregman signing – reportedly five years, $175 million, with $70 million of that deferred into future years – we knew the Cubs’ front office was operating with a different philosophy in this particular signing.
The question, which was expressly asked of Cubs President of Baseball Operations Jed Hoyer at today’s presser, is whether that was something limited to Bregman, or whether it reflected a real change.
It was pretty clearly the latter.
Hoyer pointed out that the Cubs have deferred some compensation before, including in the Jason Heyward and Jon Lester deals, but conceded that it wasn’t something they were doing much before this offseason. We already knew this, of course, because Hoyer and Cubs Owner and Chairman Tom Ricketts had been pretty transparent about not wanting to have payments scheduled way out in the future on the books for players who aren’t in the organization anymore. Understandable, I suppose, when you put it that way, but we’ve always talked about how these are merely financial instruments. Done right, they can be as much a benefit to the team as to the player and his agent. A refusal to use them, when it’s clear that the top free agents and top agents want to have that flexibility, could have been a real impediment to the Cubs getting these kinds of signings in the door.
Thus, Hoyer said, he had conversations through the last year with Ricketts and Cubs Business President Crane Kenney about their philosophy on deferred payouts. They were productive, fruitful talks, and it ultimately led to the group thinking about contract structures and financial engineering a little differently this time around. Organizations have to evolve if they want to stay successful.
To be clear, Hoyer didn’t explicitly say that he was making the case with ownership throughout the year that the front office needs to be able to offer these kinds of deals, but that’s kind of how it felt. Given that we know how badly Hoyer and the front office wanted to sign Alex Bregman last offseason, and given that they came up short with an offer that included no deferrals and was arguably less attractive than a heavily-deferred (with multiple opt-outs) offer from the Red Sox, you could even think about the entire process of courting Bregman twice being a factor in this evolution in financial thinking. It’s not exactly too little, too late, but I’ll be over here thinking of what might’ve been if the Cubs had simply offered this kind of deal last time around. They may have had Bregman a year earlier, AND they may have had him on a BETTER deal going forward. No one involved wants to see that kind of mistake again.
So, then, I believe I was correct to say, in analyzing the Bregman signing, that we can now think a little differently about the kinds of moves the Cubs are able and willing to make in free agency. It doesn’t mean they’re going to be a Mets or Dodgers or Yankees-like behemoth every offseason in the spending column, but at least they aren’t going to be taking themselves out of the bidding on some of the best names by erecting an unnecessary road block. The philosophy has changed, and, although we could intuit it from the Bregman signing, Hoyer all but confirmed it today at the press conference.
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