Dream Cubs roster for 2026 if Jed Hoyer silences the hate at the Winter Meetings

The Winter Meetings have arrived, and they allow for Chicago Cubs fans to dream big. With the Cubs coming off their first playoff season in a 162-game season since 2018, one would think this winter would be used to fully open the team's contention window.

With clean books moving forward, a need in their rotation, and looking for a way to replace Kyle Tucker's impact, one, under normal circumstances, would point to the Cubs as being among the most active teams this week.

The reality of the situation is that the Cubs are still being cautious about how much they spend this offseason, and they may not have the prospect capital to pull off a trade for someone like Tarik Skubal.

Dream Cubs roster for 2026 if Jed Hoyer fulfills wishes at the Winter Meetings

Starting Rotation (5)

• Keeping: Cade Horton, Justin Steele, Matthew Boyd, Jameson Taillon
• Adding: Joe Ryan
• Cutting: Shota Imanaga

If the Cubs do nothing else this offseason, they had better come away with a top-of-the-rotation starting pitcher this offseason. Dylan Cease is already off the board, and his deal with the Toronto Blue Jays likely pushes Chicago further away from the likes of Framber Valdez and Ranger Suarez. Michael King wouldn't be a bad fallback option, but the Cubs need to aim higher.

That is where Ryan comes into play. Ryan is among the best arms available on the trade market, and likely would require the Cubs to trade from not only the top of their farm system, but also from their Major League roster (more on that later).

It seems overreactionary to point to Imanaga's struggles in September and the playoffs last season and say that he isn't capable of being the All-Star pitcher he was during his first season and a half with the Cubs. That said, if it's a question of him or Ryan, the Minnesota Twins' ace is the answer every time.

Bullpen (8)

• Keeping: Daniel Palencia, Phil Maton, Colin Rea, Porter Hodge, Luke Little, Ben Brown
• Adding: Hoby Milner, Brad Keller
• Cutting: Javier Assad

The Cubs acted swiftly to sign Phil Maton to a two-year deal this offseason, but they still have some heavy lifting to do. Outside of Palencia, none of the high-leverage relief pitchers that Craig Counsell used last season are currently on the roster.

With the Baltimore Orioles signing Ryan Helsley and the New York Mets adding Devin Williams, there might have been a slight uptick in the Cubs' chances of bringing back Brad Keller. It likely will require a multi-year deal, but the team has the space for that type of deal. Short of a left-handed option, Milner is someone Craig Counsell knows well and likely wouldn't be that expensive.

At the end of the 2025 season, it felt like the Cubs ran out of their belief that Assad can pitch above his metrics. It's hard to view as anything other than a depth option next season, if that.

Infield (5)

• Keeping: Carson Kelly (C), Michael Busch (1B), Nico Hoerner (2B), Dansby Swanson (SS)
• Adding: Alex Bregman (3B)
• Cutting: Matt Shaw

If the Cubs plan on adding an offensive upgrade this offseason, it likely would be at third base. Considering the interest they had in Alex Bregman last offseason, it makes sense they would be circling again this winter.

The Cubs would be wise not to ignore Matt Shaw's slump at the end of the regular season and in the playoffs. There certainly is a scenario where the Cubs sign Bregman and move Shaw in a utility role, but adding the All-Star third baseman may also make the young infielder a trade chip this offseason.

Outfield/DH (4)

Keeping: Ian Happ (LF), Pete Crow-Armstrong (CF), Owen Caissie (RF)
Adding: Byron Buxton (DH)
Cutting: Seiya Suzuki

Yes, Seiya Suzuki has a no-trade clause, but when there was talk about him possibly being on the move last offseason, it's important to remember that his camp didn't completely shut down the idea of Suzuki moving out of Chicago.

Buxton would be a dream addition to the Cubs' starting lineup, and considering he is earning $15.1 million in each of the next three seasons, his contract is far from a burden. In fact, it may be a steal if Buxton puts up the numbers as he did in 2025, 35 home runs and 136 wRC+.

Bench (4)

• Keeping: Miguel Amaya (C)
• Adding: Ryan Mountcastle (1B), Kiké Hernández (UTILITY), Rob Refsnyder (OF)
• Cutting: Moises Ballesteros

In an offseason where the Cubs, in theory, would be trading for both Ryan and Buxton from the Twins, it's hard to imagine they come away from that deal with Moises Ballesteros still on their roster.

Michael Busch should start getting starts against left-handed starters next season, but adding a right-handed backup like Ryan Mountcastle would raise the floor of the bench. As would the addition of a capable utility infielder in Kiké Hernández. As a right-handed hitting outfielder, Refsnyder would offer some balance for Caissie in right field.