After making the postseason for the first time in five years, Jed Hoyer and the Cubs are looking for more. Michael Reaves / Getty Images
The 92 wins the Chicago Cubs accumulated this season marked a nine-game improvement and the return of October baseball to a jam-packed Wrigley Field. As a wild-card team, the Cubs also fell nine postseason wins short of winning the World Series.
Closing that gap will be an overarching idea for Cubs president of baseball operations Jed Hoyer and his front office over the coming months. The offseason begins in earnest now that the Los Angeles Dodgers defended their title by beating the Toronto Blue Jays in Saturday night's epic Game 7.
Bulking up the pitching staff is one way to reshape a playoff team that ran out of fresh, trusted arms in October. With no indications that the Cubs are prioritizing Kyle Tucker's return -- and no reason to think the All-Star outfielder will have to settle for a club-friendly, short-term deal -- pitching will continue to be the focus.
This class of free agents is projected to include Framber Valdez, Dylan Cease, Michael King, Zac Gallen and Shane Bieber, and the Cubs have a proven formula for identifying starters who can work within a game-planning system that highlights a pitcher's individual strengths and features Gold Glove defenders all over the field.
The Cubs, though, have not made a nine-figure commitment to a pitcher since signing Yu Darvish around the start of spring training in 2018 -- and the club dumped that contract halfway through a six-year, $126 million deal, in the middle of a pandemic.
Outside of presenting to Shohei Ohtani -- who was going to sign with the Dodgers anyway -- and engaging with Trea Turner, the Cubs have avoided almost all of the tip-top free agents in recent years. The Cubs did not take part in the negotiations that led to Yoshinobu Yamamoto's 12-year, $325 million contract with the Dodgers. Nor did the Cubs enter the $765 million Juan Soto sweepstakes.
The Cubs still have the capacity to make seismic moves. No one saw it coming when Hoyer decided to fire former manager David Ross and hire Craig Counsell away from the Milwaukee Brewers. Trading for Tucker ahead of his walk year was a bold action.
The Cubs, though, stopped short of going all in to win the World Series, and club officials would reject that concept by insisting that the way to win a championship is by consistently qualifying for the playoffs. For now, this measured business/baseball model still appears to be in place, given ownership's conservative philosophy, Hoyer's recent contract extension and the uncertainty surrounding a collective bargaining agreement that expires after the 2026 season.
Without making a single offseason transaction, the Cubs could field a reasonably competitive team that would likely be in the hunt for a wild card. That, of course, would be the bare minimum and not the ultimate goal.
Hoyer's front office is always "solving for wins," as Counsell might say. Presuming Tucker signs with another team this winter, the Cubs will explore different ways to replace his production, whether it's finding a big left-handed hitter or pivoting toward an upgrade at third base. Another right-handed hitter will need to be added to the mix.
The rumors surrounding Kyle Schwarber, Alex Bregman and the Cubs will percolate this winter.
With nearly five months to go until Opening Day 2026, the Cubs also have close to a full complement of position players:
1B: Michael Busch
2B: Nico Hoerner
SS: Dansby Swanson
3B: Matt Shaw
C: Carson Kelly/Miguel Amaya
LF: Ian Happ
CF: Pete Crow-Armstrong
RF: Seiya Suzuki
DH: Moisés Ballesteros/Owen Caissie
Even before making decisions on the contractual options involving Shota Imanaga and Colin Rea, the Cubs have the makings of a reliable starting rotation for next season: Matthew Boyd, Cade Horton, Jameson Taillon, Javier Assad and Justin Steele (assuming he doesn't experience any setbacks after undergoing elbow surgery last April).
Once again, the bullpen will need a makeover, but Cubs officials view that churn as an opportunity to find the next Brad Keller, Drew Pomeranz and Caleb Thielbar, who were under-the-radar additions before becoming valuable relievers at Wrigley Field.
This is also the complete list of Cubs players on a fully guaranteed contract after the 2026 season: Swanson.
Perhaps the Cubs are not approaching the same cliff Hoyer saw off in the distance when he took over for Theo Epstein after the 2020 season. This group also has not come close to reaching the same heights as that core group of players from the 2016 World Series team.
The counterargument to Hoyer's "clean books" strategy is that the Cubs might run the risk of not having enough good players to be a sustainable contender.
In blanching at the cost to upgrade the rotation last summer, Hoyer insisted the Cubs would have had to subtract a valuable piece from their major-league roster and give up one of the sport's top 100 prospects.
The implication being that the sellers at the trade deadline wanted Shaw or Horton -- plus a young hitter such as Ballesteros or Caissie -- in exchange for a starting pitcher who would be under club control for multiple pennant races.
As an organizational rallying cry, Hoyer's rationale was not quite as stirring as Epstein's memorable justification for the 2016 Aroldis Chapman trade: "If not now, when?"
Across the baseball industry, though, front offices are now generally more cautious and less inclined to do those types of blockbuster deals. Still, this could be a good time to revisit those trade talks and see what has changed.
Since their interim general manager listened to offers for All-Star pitcher MacKenzie Gore around the trade deadline, the Washington Nationals hired a 35-year-old president of baseball operations, Paul Toboni, to oversee their prolonged rebuild.
The Minnesota Twins were still up for sale last summer when it seemed as if they had traded everyone but All-Star pitcher Joe Ryan. By the middle of August, the Pohlad family had announced a plan to retain the franchise and bring on new investors.
The Miami Marlins decided against a full sell-off last July, but if they try to move Edward Cabrera this winter, the Cubs would almost certainly have interest. Sandy Alcantara is another name to file away, as the former Cy Young Award winner started to look more like a top-of-the-rotation starter in the second half, regaining his form after Tommy John surgery.
Ryan, Gore and Alcantara are positioned to become free agents after the 2027 season. Alcantara's contract comes with a $21 million team option for 2027, and Cabrera won't be a free agent until after the 2028 season. While the Marlins might try to speed up their competitive timeline, it's anyone's guess when the Nationals and Twins are planning to be serious playoff contenders again.
This will also be an opportunity to see if the perception of Chicago's farm system has changed. Though the Cubs developed young talent at the major-league level this year, their farm system is still lacking in pitching prospects who move the needle.
Even before Imanaga threw the first pitch of the 2025 season toward Ohtani, the Cubs had compiled substantial scouting reports on the upcoming waves of players expected to leave Japan for the next challenge.
In Hoyer's mind, the Tokyo Series represented the culmination of the organization's long-running efforts to establish connections in Nippon Professional Baseball, highlight the Cubs as a brand overseas and turn Chicago into a destination for Japanese players.
At this point, it's unclear exactly how the Cubs will value and prioritize this anticipated group of international free agents. Imanaga, for example, sort of fell into their laps while he made the Chicago area his temporary base before picking a new team. The Cubs were also prepared for that opportunity, collecting enough information to present an individualized pitching plan and make a sound investment.
A similar process could make them players for Tatsuya Imai, a 27-year-old right-hander with a long track record of NPB success.
Foster Griffin, a first-round pick of the Kansas City Royals in 2014, reinvented himself with the Yomiuri Giants, going from a pitcher at the bottom of a major-league 40-man roster to an intriguing free agent.
Munetaka Murakami, 25, is a powerful left-handed hitter who has been tracked extensively by both New York teams; the Mets and Yankees are among that small handful of clubs with a consistent presence in Asia.
As with Murakami, there are doubts about whether Kazuma Okamoto could handle third base, but his right-handed presence could bring some balance to a lineup. It's just harder to see the Cubs aggressively pursuing a 29-year-old first baseman.
Perhaps the roster fits and price points aren't ideal for each of those players. But the Cubs have positioned themselves to be involved in any of these conversations and be seen by Japanese talent as a credible option.