Inside the Cubs offseason: Bregman fever and how they stack up against the Brewers

This past week has brought about major excitement in the Chicago Cubs fanbase. After a bold trade for Edward Cabrera, which reinforced a deep rotation, All-Star third baseman Alex Bregman is now on his way to the North Side, inking a landmark five-year, $175 million contract (with $70 million deferred).

The offseason began on uncertain ground amid Kyle Tucker’s imminent departure, but president Jed Hoyer has delivered the moves necessary to keep Chicago competitive. But is this Cubs roster positioned to finally take down the Milwaukee Brewers in the NL Central? Let’s dive in.

What moves have the Cubs made so far?

(You can read the full list of transactions, which includes Minor League contracts and Rule Five purchases, at MLB.com.)

Chicago spent the first month and change of free agency spamming bullpen upgrades, which was much needed. The bullpen has been a weight around the Cubs’ neck for too long. All five of Chicago’s signings — Hoby Milner, Caleb Thielbar, Hunter Harvey, Jacob Webb, Phil Maton — posted sub-4.00 ERAs last season and should contribute substantially in 2026. Chicago’s bullpen went from a weakness to a potential strength in a flash.

The highlights, however, came in the last week.

Chicago trading for righty Edward Cabrera reinforces the rotation in a big way. Cabrera still needs to iron out some command issues, but his stuff is top-notch — especially in the off-speed department. The Cubs still don’t have a proper ace, but Justin Steele should return from elbow surgery midseason, and there’s a lot to like between Matthew Boyd (an All-Star in 2025), upstart MLB sophomore Cade Horton, and Shōta Imanaga. Jameson Taillon is a strong No. 5, while Colin Rea is one of the better swingmen in MLB.

That’s not to say the Cubs’ rotation is bulletproof. Boyd and Imanaga are both pitch-to-contact vets who regressed down the stretch of last season. Neither was dependable in the playoffs. Meanwhile, Steele is the closest Chicago has to a bonafide No. 1 ace, and there’s no telling what to expect upon his return from such a major injury.

Those questions are mitigated somewhat by the Alex Bregman signing, which solidifies the Cubs’ offense to extent that few anticipated coming into the offseason. We knew Kyle Tucker was out, but the Cubs are historically risk-averse to a fault. Giving Bregman $35 million annually, even with significant deferred money, is uncharacteristic of Hoyer and this front office. Credit for making a splash when needed.

Tough choices loom for the Cubs

Is Nico Hoerner as good as gone after the Alex Bregman signing?

This Cubs lineup looks airtight on paper, with Bregman, Dansby Swanson, Nico Hoerner and Michael Busch forming one of the most well-rounded infield cores in MLB. But what about former top prospect Matt Shaw, whose bat really picked up steam down the stretch of last season. The season-long numbers weren’t great — .690 OPS and 98 OPS+ — but Shaw is only 24 and due for a breakout sooner than later?

Well, it sounds like the Cubs might bump Shaw to second base and shop the expiring contract of Hoerner. Hoerner was awesome last season, hitting .297 with a career-best 114 OPS+, all while providing his standard, Gold Glove defense at second base. His 4.8 fWAR was second on the Cubs current roster, trailing only Pete Crow-Armstrong.

Chicago can get a nice haul for Hoerner, and it clears the path for Shaw to properly break out at a less demanding defensive position. Is that the best move for the Cubs’ 2026 World Series aspirations? Maybe not. A Hoerner trade is certainly not a given. But, as Chicago attempts to balance the books and look toward the future, a Hoerner trade is definitely in the cards. Expect the Yankees, Red Sox, Phillies and other infield-needy teams to take interest in the speedy second baseman.

Will the Cubs target a star closer?

Chicago has stockpiled rock-solid relievers all winter, but the Cubs’ bullpen lacks the star-power of other relief units around the National League. Daniel Palencia was a huge revelation in the closer role last season, but he’s not on the level of Jhoan Durán, Edwin Díaz, Raisel Iglesias or Abner Uribe. He slings bullets and the stuff pops, but when Palencia gets hit, he gets hit hard.

The Cubs are probably done with their bullpen for now, and Palencia is still an above-average closer. But one can’t help but wonder if Chicago really goes for it if the right trade becomes available. Mason Miller’s name has been floating around of late. San Diego needs prospect depth and starting pitching. Just put this thought on the back burner.

What does the future hold for Ian Happ?

Ian Happ is another Cub on an expiring contract. Having spent his entire nine-year career on the North Side, Happ put together arguably his best all-around campaign yet in 2025. He put up a .762 OPS and 120 OPS+, ripping 23 home runs and earning his fourth straight Gold Glove award in left field. On paper, he’s as essential as any non-PCA Cub.

But what exactly does the future hold? In all likelihood, Happ plays out the final year of his contract and tests the open market. The Cubs aren’t going to shell out a lucrative extension, and Happ is too valuable to trade… right? Seiya Suzuki and Pete Crow-Armstrong figure to occupy right and center field, respectively. Then there’s No. 4 Cubs prospect Kevin Alcántara, who made cameos in 10 games last season. He went 4-for-11 with a walk and a stolen base.

Alcántara is a potential five-tool star, providing speed on the bases, range in the outfield, and serious thump with his bat. At 23, you’d like to think he’s more than a backup — and he’s due for a breakout in MLB. The Cubs probably wait until 2027 to fully unleash Alcántara, but if he forces the issue, fascinating questions arise. Suzuki might get boxed out of the DH spot by top prospect Moisés Ballesteros. The outfield depth chart is loaded; that’s why the Cubs were comfortable trading Owen Caissie, their No. 1 prospect, to Miami in the Cabrera deal. Does Happ become available? That will depend, of course, on his own performance. But this is bubbling under the surface.

It’s more of an offseason question if all goes to plan, but just keep Alcántara. The flip side of this: if Happ plays well and the Cubs’ outfield rakes, it could be Alcántara who ends up as a premium trade chip to potentially facilitate a pitching upgrade or another big addition at the deadline.

The Cubs rotation could still use one more facelift

Chicago has depth on the mound, but again, Cabrera is not entirely trustworthy. He was a worthwhile gamble, to be clear, but the Cubs can’t necessarily depend on him as their sole addition. Both Imanaga and Boyd are on the downturn. Rea and Taillon aren’t on the upswing either. Other than Horton and maybe Steele, it’s unclear who the Cubs can fully trust once October rolls around. Adding a proper, full-blown star to the top of the five-man chart would go a long, long way.

The Cubs are probably settled for now. Major trade candidates, like Freddy Peralta, Tarik Skubal and Joe Ryan, probably aren’t in the cards this offseason. But what about the trade deadline? I’d imagine the Cubs end up in the market for a short-term boost, at the very least. This will be an ongoing storyline, even if Cabrera delivers on the hype. You can never have too much quality pitching.

How do the Cubs stack up against the Brewers?

The Cubs were the heavy favorites to win the NL Central last season, but Milwaukee exceeded all expectations to not only claim the division crown, but also the best record in baseball. This Brewers organization is a shining example for all small-market clubs. Milwaukee almost never doles out the big long-term extension. The Brewers don’t sign the marquee free agents. But their internal development, and their ability to find value on the margins, is virtually unmatched.

Pretty much the entire Brewers roster is due back in 2026. There remains a chance that ace Freddy Peralta gets dealt, but Milwaukee has a battalion of quality young arms coming up behind him. Jacob Misiorowski flashed Cy Young potential last season. Logan Henderson has some stuff. Brandon Woodruff is healthy. This Milwaukee rotation will get the job done.

Meanwhile, the Brewers’ offense is the perfect encapsulation of death by a thousand paper cuts. They don’t hit for a ton of pop, but their swing decisions, one through nine, are airtight. The Brewers manufacture runs the old-fashioned way, and while that strategy produces mixed results in the postseason, it tends to translate to a lot of wins in the regular season. There just is not much negative variance.

How Cubs can close gap on Brewers

That is where the Cubs hope to close the gap. This offense has a ton of firepower. PCA’s second-half regression set off alarm bells, but he still 31 home runs — with significant room for growth in his age-24 season. Michael Busch and Seiya Suzuki hit 34 and 32, respectively. Happ hit 23. Bregman, Carson Kelly and Moises Ballesteros should all cruise past 20 homers in a full, healthy season.

Chicago has more discipline issues, more violent swings between positive and negative, but the ceiling offensively is much higher. If the Cubs can slug at max capacity, with a solid rotation and a bolstered bullpen, there’s no reason this North Siders squad can’t give Milwaukee a run for its money.

Are the Cubs favorites after the Bregman and Cabrera moves? It’s certainly a conversation. I’d prefer a bit more top-end talent on the pitching front, but Chicago has very few true weak points. Their ceiling, particularly on offense, is exciting. The Cubs feel like a clear top-four squad in the NL, up there with L.A., Milwaukee and Philadelphia. That’s a good place to be, especially after where the offseason started: shrouded in Kyle Tucker-adjacent uncertainty.

The Cubs are on the come-up. If Craig Counsell can exorcise his Brewers demons and get this team playing up to its potential, Milwaukee needs to watch out.