A brutal loss in Game 5 of the NLDS to the Milwaukee Brewers starts the offseason on the North Side, with plenty of changes to be expected for next year’s team.
The 2025 season has officially come to an end for the Chicago Cubs, with a Game 5 loss in the NLDS closing the curtains on a 92-win season that saw the North Siders win a playoff series for the first time in eight years.
While the season had undoubtedly the best showing from the Cubs this decade, impending free agency to key players and a division rife with young talent make getting back to this point easier said than done.
Chief among the offseason questions for the Cubs will be what to do with Kyle Tucker, unquestionably the biggest prize on the free agent market and a pivotal part of the Cubs’ success in the first half of 2025.
Yet beyond Tucker, the Cubs are approaching an inflection point for this group of core players with the 2026 season on deck. Most notably, Ian Happ, Seiya Suzuki, Nico Hoerner and Jameson Taillon are all on expiring contracts in 2026, making this offseason imperative for aiming to extend any of the franchise mainstays.
The Cubs are also confronted with a farm system that pales in comparison to their four division rivals, with the system seeing a sharp drop-off beyond the top-level talent of Owen Caissie and Moises Ballesteros. While the North Siders retain long-term team control over multiple starters, namely Michael Busch, Matt Shaw and Pete Crow-Armstrong, there’s still plenty of room to solidify a group that remains one major injury away from completely different expectations.
Though this offseason’s free agent market is far from the most robust seen in recent years, there remain plenty of opportunities for the Cubs to shore up their roster with the available talent.
Before getting into possible Cubs targets this offseason, I do want to establish my current opinion on any potential pursuit of a reunion with Kyle Tucker.
While Tucker is unquestionably one of the league’s finest hitters and a solid defender when healthy, a steady flow of recent injuries and a middling performance in the second half and postseason gives me a little trepidation when considering what a long-term deal with Tucker would look like.
With the Cubs having never exceeded the value of Jason Heyward’s eight-year, $184 million deal signed before the 2016 season, it’s hard to see and justify the Cubs likely going over double that amount for a player that while incredible, is not entering this offseason with a track record of durability.
As Tucker stands out as the clear top target for teams in this year’s market, Cubs fans shouldn’t expect to see a record-breaking contract shelled out to anyone else this offseason, though there should still be room for at least one pursuit of a major free agent.
Here’s a look at three possible targets the Cubs should go beyond doing their due diligence on this offseason, though I don’t think there’s a plausible scenario in which all of these players are signed. Rather, take this as a look at the different paths the Cubs could take on the free agency market this offseason.
1. Kyle Schwarber, DH
Considering the Cubs’ history of staying below $200 million contracts in free agency and the monumental deal Kyle Tucker is likely to secure this offseason, the focus should start with plans to replace Tucker’s production in the lineup.
There would be no easier way to do that than to pursue a reunion with Kyle Schwarber, the to-be 33-year-old designated hitter who just led the National League with 56 home runs in 2025.
While an established power hitter during his time with the Cubs, Schwarber has become a generational slugger since leaving the North Side, hitting 219 of his 340 career home runs in the past five seasons.
Schwarber has also become more formidable at the plate due to his improved patience in recent seasons, help offsetting the inevitable frequent strikeouts. After topping out at 78 walks in a season with the Cubs in 2018, Schwarber has walked at least 106 times in each of the past three seasons, including a 126-walk season in 2023.
With that said, Schwarber has plenty of drawbacks which will bring his price to a lower point than perhaps one would expect for a guy that just hit 56 home runs. While Schwarber has plenty of experience as a left fielder in his career, he routinely ranked among the league’s worst defenders at any position and shouldn’t be counted on to contribute defensively.
In the event of the Cubs going after Schwarber in an effort to replace Tucker’s production, this would almost certainly mean a full-time return to right field for Seiya Suzuki, with Schwarber taking the role of a full-time DH, something that will likely be the case regardless of where he signs.
I don’t think this is an incredibly realistic outcome, despite the obvious fit in the event of Tucker signing elsewhere. While Philadelphia’s early playoff exit may change the front office’s approach a little, there’s no question that Schwarber is beloved by the Phillies and that the team will at least explore what a reunion could look like.
For the Cubs, pursuing a three-to-four year deal with Schwarber in the $90 million to $100 million range may feel aggressive, but that may be required if the Cubs look to reunite with the 2016 World Series champion.
2. Luis Robert Jr., OF
This target is contingent on two things – of course the Cubs not signing Tucker and looking to replace his production, as well as the White Sox declining his $20 million club option, which includes a $2 million buyout.
I’m of the belief that both of these things will occur, especially considering the White Sox’s history as a frugal franchise combined with Robert Jr.’s decreased production the past two seasons and an emerging core of new young talent.
The last holdover from the 2021 division-winning team, Robert Jr. has been objectively underwhelming the past two seasons after finishing 12th in AL MVP voting with a Silver Slugger Award in 2023.
The numbers have been strikingly similar – an OPS+ of 86 and 85 over the past two seasons, respectively, with 14 home runs in both years as well. Robert Jr. did show some added utility on the basepaths in 2025, however, swiping a career-high 33 bags.
While this downturn could be one that Robert Jr. doesn’t bounce back from, I believe that at least some of the diminished performance could be attributed to poor morale after playing for the worst team in modern MLB history followed by another 102-loss team.
When on, Robert Jr. is truly a five-tool superstar, something that has been on display at various times throughout his career, most prominently in his 38-homer, 20-steal campaign in 2023. On top of unquestionable power and sneaky effective speed, Robert Jr. is also an excellent outfield defender. The 28-year-old has posted 3.6 defensive WAR in his career thus far, and won a Gold Glove as a rookie in the pandemic-shortened 2020 season.
If the Cubs were to pursue Robert Jr., it would come with one significant change for the crosstown rival – a move from the position he has exclusively played at the big league level in center field. With no plausible circumstance that Pete Crow-Armstrong would be moved away from center field, the Cubs would likely aim to convince Robert Jr. to take over in right field while keeping Suzuki as a DH in the event of a pursuit.
Assuming Robert Jr. hits the market, this does feel like a flyer-type move the Cubs have made in the past. Robert Jr. will likely be in line for a deal of one-to-two years and probably won’t require a lofty financial guarantee.
3. Dylan Cease, SP
Originally a Cubs farmhand, Cease was a major component of a 2017 crosstown blockbuster deal that sent left-handed starter Jose Quintana to the North Side. Debuting with the White Sox in 2019, Cease spent five years on the South Side before playing the last two seasons with the San Diego Padres.
Entering his age-30 season, Cease has been pretty consistent through his seven-year MLB career, despite his stats looking a bit more like a mixed bag at first glance.
Though his ERA in a full season has ranged between 2.20 and 4.58, there have always been a few certainties with Cease: he’s going to both walk and strike out a ton of batters, reliable to make 30+ starts a year but won’t routinely go particularly deep into games and can have no-hit stuff on any given night.
The strikeouts alone tell plenty of the story with Cease, and there’s no reason to believe it won’t continue barring major injury. Despite not pitching more than 189.1 innings in a season, Cease has posted at least 214 strikeouts in each of the past five seasons, topping out at 227 in 2022.
While the walks will always remain a part of Cease’s game, the righty’s proven track record of being a strikeout specialist feels much needed on a Cubs pitching staff that was noticeably lacking of a skillset like Cease in 2025.
As a whole, the Cubs’ pitching staff finished 27th of 30 teams in strikeouts in 2025, nearly 100 strikeouts lower than the closest fellow playoff team in the Boston Red Sox, who were 16th across the league.
Adding a reliable starter who is guaranteed to put away batters at a stifling pace when healthy would work wonders for a Cubs rotation that was lacking of a true juggernaut with pitches that could blow away opposing hitters.
This isn’t to say Cease is the best pitcher in the game, with his spotty control being an obvious risk and drawback of a long-term contract, but he can be the best pitcher in the game on any given night. In order to succeed in the playoffs, having at least one starter on the pitching staff with that capability and reputation can make a world of difference when the lights are the brightest.
If the Cubs were to get back a healthy Justin Steele next season that resembles his pre-injury form, the North Siders could suddenly have one of the stronger rotations in the sport in the event they added Cease.
While there will likely be plenty of teams interested in Cease’s services and the Cubs typically aren’t known to spend big, this actually does feel like a move they could make. The Cubs have previously demonstrated interest in their former farmhand, and may be more willing to make their big move on pitching assuming the North Siders decide not to pursue Kyle Tucker.
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