It remains to be seen exactly how much the Chicago Cubs’ playoff run will boost the 2026 budget for baseball operations, and whether the energy from those raucous crowds at Wrigley Field transfers into a hyperactive offseason.
Following a quiet Winter Meetings, part of that agenda falls within the purview of ownership and the business side of the organization, the degree to which the Cubs want to act as a big-market franchise, as well as the calculus for making investments in the final year of the sport’s collective bargaining agreement.
From a baseball standpoint, there is one major postseason takeaway.
“You can always say there’s never enough pitching,” Cubs manager Craig Counsell said. “If you look at what happened to us in the playoffs, if we would have had to keep going, that’s where I think it would have got daunting.”
That’s why the Cubs are so focused on adding another quality starting pitcher, even after Shota Imanaga’s decision to accept the one-year, $22.025 million qualifying offer.
Playing four elimination games in October drained Chicago’s pitching staff, which was simply not set up to beat the Los Angeles Dodgers in a best-of-seven National League Championship Series. Even under ideal circumstances, it would have been difficult to topple a dynasty.
Game 5 of the National League Division Series was the fourth elimination game of the playoffs for manager Craig Counsell and the Chicago Cubs. (Michael Reaves / Getty Images)
The Cubs had worked around Justin Steele’s season-ending elbow surgery in April to finish with 92 wins, which represented a nine-game improvement from the previous year as well as a five-game deficit in the NL Central.
That forced the Cubs into the wild-card round and handed home-field advantage to the Milwaukee Brewers. Two rotation stalwarts, Matthew Boyd and Jameson Taillon, helped the Cubs eliminate the San Diego Padres and force a decisive Game 5 in Milwaukee.
At that moment, the Cubs did not fully trust Imanaga, and Cade Horton was sidelined with a fractured right rib. Horton progressed to the point where the Cubs would have activated him if they had advanced to the NLCS. But even that development came with a caveat: The club would have used him in only a limited capacity.
“I don’t think it was daunting for the first two series,” Counsell said. “And I don’t think it necessarily affected us for the first two series. If we had to keep going … it would have been difficult.”
• Losing Game 7 of the World Series motivated the Toronto Blue Jays to sign Dylan Cease to a seven-year, $210 million contract and keep pushing. The Cubs were involved in the Cease negotiations — at least until it became clear that agent Scott Boras would close a deal well beyond their comfort zone.
Cease is a supremely talented pitcher with swing-and-miss stuff (200-plus strikeouts in each of the past five years) and a strong track record of durability (32 or 33 starts each season during that period). He also once made a favorable impression as a prospect in Chicago’s farm system, demonstrating a good work ethic and curiosity about pitching development.
Cease also didn’t put together a great platform season with the Padres (8-12, 4.55 ERA), nor does he have much of a postseason resume. But the demand for high-end pitching potential is so robust that he reached an agreement on a monster contract before Thanksgiving.
During the Winter Meetings, the Philadelphia Phillies made an enormous five-year, $150 million commitment to Kyle Schwarber, a designated hitter who will be 33 years old next season. Pete Alonso, a first baseman/designated hitter who lingered on the free-agent market for months last offseason, then secured a five-year, $155 million deal with the Baltimore Orioles.
Reloading their bullpen, the Dodgers shrugged off the disappointing start to Tanner Scott’s four-year, $72 million contract and signed All-Star closer Edwin Díaz to a three-year, $69 million deal.
In reading the market, Cubs general manager Carter Hawkins said those early prices have not created a sense of sticker shock.
“Those always happen,” Hawkins said. “What’s the market rate for a deal? That’s the average, and there’s going to be some extremes on both sides. Typically, there’s not many players that are going off the board early that didn’t get a deal that they really liked, so you always kind of withstand that first rally.
“What was the context of that player? Who were the different teams that were (pursuing) him? And what did they need to do in order to get him? Sometimes, there are these perfect storms that really work out well for a player.”
• Right now, the Cubs have a rather thin group of pitching prospects, which partially explains why the front office keeps looking for an accomplished starter, possible swingmen and bullpen reinforcements.
One name, however, is firmly on the radar for 2026. The club hopes that Jaxon Wiggins could make the kind of leap to Wrigley Field that Horton just experienced.
“That’s obviously a high bar,” Hawkins said. “If he could do half of what Cade Horton did, that would be awesome. But I think he’s shown that he can get upper-level hitters out. It’s really just getting over the health and the command hurdle. If he does that, he’s got a chance to help us out.”
Wiggins did not pitch for the University of Arkansas during the 2023 season after undergoing Tommy John surgery. But the 6-foot-6 right-hander still had the powerful size and stuff that convinced the Cubs to grab him in the second round of that year’s draft and give him a $1.4 million bonus.
Load management factored into this year’s plan for Wiggins, who accounted for 78 innings at three different minor-league affiliates combined, finishing the season at Triple-A Iowa. A similarly detailed, conservative approach helped Horton bounce back from previous health issues and become one of the best pitchers in the majors after the All-Star break.
Each pitching program is also individualized, and progress may not be linear. Horton exceeded all expectations with a second-place finish in the NL Rookie of the Year voting, a performance that will not be easily replicated. But in terms of raw ingredients to work with, Hawkins described Wiggins as someone who “can jump out of the gym from an athleticism standpoint.”
“A lot of explosiveness,” Hawkins said, “(with) a breaking ball that’s going to miss bats and a fastball that’s going to miss bats. He’s turned that up into the upper 90s and into the 100s. It’s really just about landing them and being consistent with the command.
“He’s just one of those guys that kind of oozes potential. It’s just a matter of corralling all of it. There’s a lot of paths for Jaxon. It could be as an upper-end starter if he’s able to command. It could be a guy you see in a bullpen at some point. It could be both.
“We’re excited to get him healthy and get a full season under his belt and see where it takes us.”
• With a chance to take over for Kyle Tucker at Wrigley Field, Owen Caissie is expected to play for Canada in the 2026 World Baseball Classic. Rather than going through the motions of spring training, the young outfielder could benefit from getting locked in faster to face a higher level of pitching and compete in an intense atmosphere.
Playing for his country in the 2023 event became a good learning experience for Caissie, a left-handed hitter who made his major-league debut last summer and has nothing left to prove at the Triple-A level.
Caissie has also been working out at the Cressey Sports Performance facility in Florida, a popular offseason destination even for established major-league players. All of this is geared toward being fully ready to hit on Opening Day in Wrigleyville.