The Stunning Signing, the Offer Structures, Plan A Offseason, and Other Cubs Bullets ...Middle East

What a weekend. I’m still spinning around a bit trying to hang onto all the thoughts that are ping-pong’ing around my head, but I expect that putting pen to paper today will help.

To that end, I’ve got a load of thoughts and reactions and analysis about the implications of the Alex Bregman signing, which will come later today (and, let’s be honest, throughout the week). Until then, some more on the deal, itself, and other Cubs Bullets …

Hand up: I did not think the Chicago Cubs would ultimately sign Alex Bregman. Well, I guess more precisely, I did not think the Chicago Cubs would sign Alex Bregman if he wound up getting a roughly-expected contract in free agency. Waiting around for a deal-deal-deal late in the offseason? Yes, that I could see. But aggressively going after him and paying at the top of the market? USING DEFERRALS?!?! No. That was not something for which there was a whole lot of evidence about the Cubs being willing to do. So when I saw the news, and the size and structure of the deal, I was stunned. Stunned. And smiling. For weeks I’d been opining, publicly and privately, about how I thought the signing would play out, given all those rumors about Bregman “getting” a deal worth much, much more than the one he signed with the Red Sox (despite the fact that he was coming off a good-not-bonkers season where he missed nearly 50 games, and got a year older). I said he would sign with some team on a deal that was initially reported as indeed beating the three-year, $120 million deal he got last time around, people would kinda freak about the size, and then 12 hours later we’d find out there were massive deferrals that make the deals far more equivalent, accounting for the aging. I was right! … It’s just that I never, ever expected the team that did the massive deferring would be the Cubs. So that was basically the best possible version of being right and also being wrong. In the end, the original deal with the Red Sox was three years and about $96 million ($32M AAV) when accounting for the deferrals in that one, and he got an opt out after each year. With the Cubs, the deal is reportedly around $150 million in present-day value over five years ($30M AAV), with no opt outs. We could probably have a debate about which deal is “better,” but the latter is not blowing away the former in the way some of those crazy rumors were suggesting. That simply never made sense. I think Bregman got a deal this time around that was completely appropriate, given all the context, and I’m very happy that it was the Cubs that volunteered to give it to him. What I think is probably less debatable is whether the Cubs stepped up their own offer from last time around. That one was reportedly four years and $115 million, with an opt out after the second and third years. Even accounting for the value of those opt outs, it feels like five years and $150 million is a step up, especially when – as a guy ages – the likelihood of actually using an opt out goes down. Some of that difference is the Cubs’ available payroll space this year compared to last year, but some of it may simply be the kind of budgetary improvement we’ve been desperately hoping would arrive at some point. Reporting out of Boston suggests the hangups in the Red Sox offer were at least $10 million in difference in the total guarantee, that difference getting even larger when accounting for longer deferrals by Boston, and the lack of a no-trade clause. From The Athletic: “A year ago, Bregman grilled the Red Sox front office with a 16-page document filled with questions on the direction of the organization, the development plan for the club’s top prospects and how Boston planned to invest and spend to bring the organization back to the postseason.” Not sure if Alex Bregman did that again this time around, but it’s fun to think about him grilling the Cubs, and them having exceptional answers about the future of the organization. The timing certainly was fun for us, at least:

The @Cubs reportedly pushed a deal across the goal-line last night while the @ChicagoBears completed their Wild Card round comeback ?? t.co/fGPbvbj8w4 pic.twitter.com/5rczRMlGcE

— MLB Network Radio on SiriusXM (@MLBNetworkRadio) January 11, 2026 Look, no disrespect to the Marlins, but imagine spending your whole career there, and then suddenly you’re traded to the Cubs, and they immediately sign a superstar of the type the Marlins would never sign in a billion years. You’d probably be loving your new team a whole lot, too:

Newest Cub Edward Cabrera reposted the Alex Bregman signing on his IG story. pic.twitter.com/Uo9rpMNRb9

— Cubs Zone (@CubsZone) January 11, 2026

Edward Cabrera is loving the new look Cubs via his IG. pic.twitter.com/0eVoPB0lgC

— Cubs Zone (@CubsZone) January 12, 2026 Speaking of Edward Cabrera, I wrote last week after the trade that, although it was very good to get the player, the secondary reason you trade prospects to get a guy like Cabrera – instead of just signing a free agent starter – is so that you can save money to be deployed elsewhere. If you don’t do that second part, you’re effectively just selling prospects for cash. The Cubs did indeed deploy that money elsewhere now having signed Alex Bregman, and that combo maneuver was pretty clearly part of the Cubs’ Plan A path this offseason. (I’m guessing Plan B would’ve seen them trying to sign Tatsuya Imai or Zac Gallen to a deal cheap enough annually that they could still justify to ownership the plausibility of signing Bregman. We know this, in part, because the Cubs DID try to sign Imai to a relatively bargain deal, and I highly doubt they were going to do that if it meant they absolutely positively could not sign Bregman.) This is missing the deferral context, which is not an insignificant note, but, generally speaking, this is correct:

I have to say, for the most part these short term deals with opt outs have worked out tremendously for Boras clients. Combined short deal + long deal:Snell – 6/$214MAlonso – 6/$185MChapman – 7/$167MBregman – 6/$205M (NPV)Rodon – 7/$183.5MBellinger – TBDMontgomery – Fail

— Joshua (@JoshuaHowsam) January 11, 2026 Tyler Austin’s time in Japan, why he kept staying, and why he’s coming back now to join the Cubs:

We’ve been talking a lot about pitching, but here’s a story about a position player ⬇️ t.co/DbvPifcDj6

— Maddie Lee (@maddie_m_lee) January 9, 2026 Ken Rosenthal goes deep on the looming arbitration battle between Tarik Skubal and the Detroit Tigers, which is not only an extreme outlier because of the distance between the sides ($32 million versus $19 million), but also is apparently likely to actually reach an arbitration hearing. The Brewers have added to their front office:

The Milwaukee Brewers hire former Minnesota Twins GM Thad Levine to be a special advisor to baseball operations.

— Bob Nightengale (@BNightengale) January 8, 2026 A completely random thought unrelated to anything:

Been thinking a lot lately about how the Houston Astros were so unfairly treated during the 2017 sign-stealing scandal. I think any player who may or may not have been involved was actually a victim, and should now be celebrated as a hero.

— Brett Taylor (@Brett_A_Taylor) January 11, 2026 MORE CUBS FROM BLEACHER NATION: Go Ad Free | Subscribe to the BN Newsletter

It’ll be #DaBears vs. the Rams in the NFC Divisional Round on Sunday!MORE ? t.co/qbwE3DgZxu pic.twitter.com/2Du2van1y2

— Bleacher Nation Bears (@BN_Bears) January 12, 2026

A Great Win, Youth is Served, Sharing is Caring, Prospect Goals Galore, and Other Blackhawks Bullets #blackhawks t.co/MGTJKLW2UO

— Bleacher Nation Blackhawks (@BN_Blackhawks) January 11, 2026

Big Night for Chicago! Bulls Dominate the Mavs, Schröder-Luka Altercation, and Other Bulls Bullets t.co/lw1V4h7Xz3

— Bleacher Nation Bulls (@BN_Bulls) January 11, 2026

Hence then, the article about the stunning signing the offer structures plan a offseason and other cubs bullets was published today ( Monday 12/01/2026 - 05:11 PM ) and is available on Bleacher Nation ( Middle East ) The editorial team at PressBee has edited and verified it, and it may have been modified, fully republished, or quoted. You can read and follow the updates of this news or article from its original source.

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