The Chicago Cubs' recent playoff journey and the early moves in free agency have left fans and analysts alike pondering the team’s future direction. But here's where it gets a little controversial—it's still uncertain how much the playoff success will influence the team's financial flexibility heading into 2026, or whether the enthusiasm from those energetic crowds at Wrigley Field will translate into a more aggressive offseason strategy.
Following a quieter stretch during the Winter Meetings, much of the decision-making now hinges on the ownership and the business side of the organization. They are evaluating how aggressively to act as a big-market team, especially considering the financial constraints of the late stages of the current collective bargaining agreement (CBA). The question remains: will the Cubs push all-in with big signings, or play it more cautiously?
From a baseball perspective, one key lesson from the postseason stands out clearly.
"You can always argue that pitching depth is never enough," said Cubs manager Craig Counsell. "Looking back at our playoff run, if we had to extend further into the postseason, I believe our pitching staff would have faced serious challenges."
This realization explains why the Cubs are prioritizing the addition of another top-tier starting pitcher. Despite Shota Imanaga's decision to accept a one-year, $22.025 million qualifying offer, the Cubs remain eager to strengthen their rotation. The grueling demands of playing four elimination games in October exhausted Chicago's pitching staff—a unit that was simply not equipped to handle a deep playoff run, especially against a powerhouse like the Los Angeles Dodgers in the National League Championship Series. Even under perfect circumstances, toppling such a formidable team would have been tough.
In 2023, the Cubs defied expectations by finishing with 92 wins, improving by nine games from the previous year and closing the gap in the NL Central standings—just five games behind the leaders. This success was achieved despite significant setbacks, most notably Justin Steele’s season-ending elbow surgery in April. The team had to navigate their way into the wild-card playoff round and ultimately distributed key responsibilities across their rotation, with veterans like Matthew Boyd and Jameson Taillon stepping up to help beat the San Diego Padres and push the series to a decisive Game 5 in Milwaukee.
At that moment, confidence in Imanaga was limited, and Cade Horton was sidelined with a fractured right rib. While Horton recovered enough to be a postseason option if the Cubs advanced farther, his usage would have been limited—mainly to preservation when needed.
"The first two series didn’t seem too daunting," Counsell added. "But if we kept going, that’s when the fatigue and depth issues would have become really apparent."
And here's where the controversy kicks in— some argue that the Cubs could and should have invested more in their pitching staff to make a deeper postseason push. Would a more aggressive approach to trades or signings in the offseason have changed their destiny? Or do the constraints of their current budget and roster mean this is the best they could do?
Regarding other teams' notable moves, the Blue Jays’ decision to sign Dylan Cease to a seven-year, $210 million deal after their World Series loss — a move that fueled more talks about the importance of pitching — was a bold statement. The Cubs were at least in the mix for Cease before his agent, Scott Boras, secured a contract that exceeded their comfort zone. Cease is known for his strikeout ability and durability, posting over 200 strikeouts yearly and making 32-33 starts annually, a rare combination of power and reliability.
While his time with the Padres and postseason resume don’t jump off the page, his high ceiling and proven talent made him a hot commodity, leading to that record-breaking agreement.
Meanwhile, the Phillies committed five years and $150 million to Kyle Schwarber, a DH who will turn 33 next year, and the Orioles secured five years and $155 million for Pete Alonso, a first baseman and designated hitter who was a lingering free agent last offseason. The Dodgers bolstered their bullpen, shrugging off earlier disappointments with Tanner Scott and instead signing All-Star closer Edwin Díaz for three years and $69 million.
Cubs GM Carter Hawkins acknowledged that these early blockbuster signings haven't caused sticker shock for him. "That’s the market rate for high-end players usually. Some contracts are extensions of the usual rhythm—there’s always a range. When players move early like this, it's often due to specific needs or perfect opportunities for teams and players to align. Sometimes, these deals just work out perfectly for everyone involved."
In terms of internal development, the Cubs face the reality of a somewhat shallow prospect pool, especially in pitching, which fuels their ongoing search for proven arms, potential swingmen, and bullpen reinforcements. One promising player to watch for 2026 is Jaxon Wiggins, a talented pitcher with a lot of upside. The team hopes Wiggins can make a leap similar to Cade Horton’s recent breakthrough.
"That’s a high standard," Hawkins said. "But if Wiggins can emulate even half of what Horton achieved, that would be fantastic. He's shown he can handle upper-level hitters, and health and command are the main hurdles right now. If he overcomes those, he has a real shot at helping us, either as a starting pitcher or as part of the bullpen."
Wiggins had Tommy John surgery in 2023, limiting his appearances, but his size, strength, and raw stuff—fireballing into the upper 90s or even hitting triple digits—have made him a highly drafted prospect. The Cubs have taken a cautious, load-management approach with him, similar to Horton’s recovery, aiming to maximize his development over a full season. Hawkins notes the potential is immense: "He could be an elite starter if he masters command, or a dominant reliever if that’s the path he takes. There's a lot of options for him, and we're eager to see him healthy and progress."
Additionally, young outfielder Owen Caissie is emerging as a key player for the future, with potential to step up partly because of his ability to replace Kyle Tucker at Wrigley in the coming years. Caissie is also preparing to represent Canada in the 2026 World Baseball Classic, an experience that could accelerate his readiness by challenging him against international competition before the grind of spring training begins.
Having made his MLB debut last summer, Caissie has nothing left to prove at Triple-A and has been training intensely at well-known facilities in Florida to fine-tune his skills. This focused preparation aims to ensure he's ready and locked in for Opening Day at Wrigley.
And so, the question remains— will the Cubs’ strategic moves, prospects, and financial decisions set them up for a true championship run in 2026, or are they still missing that one crucial piece? As the offseason unfolds, fans and analysts will debate: is this team on the cusp, or is there more work to do? Share your thoughts—are the Cubs headed in the right direction, or do you think they should go all-in now?
