Ranking Cubs Most Significant Offseason Acquisitions Ahead of 2026 MLB Season

The Chicago Cubs have had a busy offseason.

Alex Bregman introduced a new Chicago Cubs player | David Banks-Imagn Images

The Chicago Cubs went into the offseason looking to make some big moves after their first taste of playoff success last October in a long time, and that is exactly what they have done.

Entering the winter, president of baseball operations Jed Hoyer knew he had one job to do: get this team back to the postseason and geared up for potentially an even deeper run this time around. Though it remains to be seen exactly how that plays out, Hoyer deserves a ton of credit, because the team is a whole lot better than it was a couple of months ago.

There have been a ton of moves, the most impactful of which could end up being the more under-the-radar ones that so often define the difference between success and failure in October. Before spring begins, though, here are the five most significant acquisitions Chicago has made so far.

5. Signed RHP Hunter Harvey to One-Year, $6M Deal

Kansas City Royals relief pitcher Hunter Harvey | Jay Biggerstaff-Imagn Images

When it comes to this slot, there are a number of relievers you could insert, including guys like Jacob Webb, bringing back Caleb Thielbar, or even snagging Hoby Milner, but the investment the Cubs made in Harvey made it clear just how much they value him.

Injuries limited the 31-year-old to just 12 appearances in 2025, which makes his 0.7 bWAR in just 10.2 innings all the more impressive. With as high a ceiling as any setup man in baseball, Harvey staying healthy would mean some massive things for this bullpen.

4. Retained LHP Shota Imanaga on $22M Qualifying Offer

Chicago Cubs pitcher Shota Imanaga | Charles LeClaire-Imagn Images

When Chicago declined Imanaga's option, which would have kept him with the team for another three seasons at a fairly reasonable figure, it appeared his tenure as a Cub was over. A couple of weeks later, though, the southpaw surprised many by accepting the qualifying offer to return.

It's no secret that Imanaga struggled mightily down the stretch – likely the main reason why his option was not picked up – but if he can get back to the version of himself he was before the second half of 2025, he is still capable of making a huge impact.

With a 3.28 ERA and 24-11 record across 54 starts in Chicago, the 32-year-old has been the team's ace for most of the last two years. Bringing him back is huge and raises the overall ceiling of the starting rotation.

3. Signed RHP Phil Maton to Two-Year, $14.5M Deal

Texas Rangers relief pitcher Phil Maton | Jerome Miron-Imagn Images

It's almost easy to forget now because Maton was signed all the way back in November, but this was the marquee addition for the bullpen, and the Cubs liked him enough to sign him for more than just a one-year deal.

With a 2.79 ERA and 1.060 WHIP in 2025, Maton is one of the best relievers in the game today and instantly becomes a piece Chicago is going to build the bullpen around. The right-hander had 81 strikeouts in 61.1 innings pitched and brings the swing and miss element to the unit that they needed.

Maton reaching his full potential could make this bullpen downright dangerous.

2. Acquired RHP Edward Cabrera in Trade with Miami Marlins

Miami Marlins starting pitcher Edward Cabrera | Sam Navarro-Imagn Images

The blockbuster swap of the winter, the Cubs sent a package headlined by their top prospect Owen Caissie to acquire perhaps their highest ceiling pitcher they've had in some time now. There were ups and downs for Cabrera in 2025, but an overall 3.53 ERA and 1.228 WHIP with nearly 10 strikeouts per nine innings represent a sky-high ceiling.

Most importantly, he is under team control for a full three seasons, giving Chicago a young potential ace who could be heading up their rotation for years to come. Cabrera will have to hold up his end of the bargain, but if he can stay healthy and perform well, this will have been a seismic move.

1. Signed 3B Alex Bregman to Five-Year, $175M Contract

L-R Scott Boras, Alex Bregman and Jed Hoyer | David Banks-Imagn Images

Was there any doubt here?

The Cubs landed not only their new third baseman in Bregman, but arguably the new face of their franchise and, without a doubt, the leader of the clubhouse moving forward. The move being the largest AAV contract in team history puts it No. 1 by default, but the impact Bregman can have justifies the price.

With a full no-trade clause in place, Bregman will be in Chicago likely for his remaining productive years, and maybe just maybe, could be the final piece the Cubs need to find their way back to World Series glory.

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