After the Milwaukee Brewers won the National League Central in both 2023 and 2024, the Chicago Cubs, no doubt threatened by the success of their rivals to the north, added superstar Kyle Tucker to their roster in an effort to dethrone the Brew Crew. An impressive start to the 2025 campaign from the Cubs left Milwaukee 5.5 games back of the North Siders when the calendar flipped to June, and Brewers fans concerned about their team’s chances of completing an elusive three-peat in the division.
However, the script quickly flipped as the Brewers caught fire, resulting in the Cubs’ division lead shrinking to just 2.5 games by the end of June. When August rolled around, the Crew was back on top of the division, a position they didn’t relinquish for the rest of the season. In the end, despite the Cubs’ addition of Tucker during the previous offseason, the Brewers continued their NL Central reign, putting an exclamation point on their divisional dominance with a defeat of the Cubs in the 2025 NLDS.
Now, Jed Hoyer and the rest of Chicago’s front office face the difficult task of not only replacing Kyle Tucker, who is almost a guarantee to sign with a new team in free agency this offseason, but also eliminating the gap that exists between their squad and the team that has won the division in four of the last five seasons: the Brewers. Despite Tucker being the Cubs’ most significant anticipated departure this winter, much of the focus for Chicago so far this offseason has been on the pitching staff.
Rumors of the Cubs shopping in the top tier starting pitching market surfaced almost immediately after the offseason began. Names like Dylan Cease, who would completely reshape Chicago’s rotation, were initially rumored to be a target for Hoyer and company this offseason. Additionally, despite adding expensive relievers not being the Cubs’ typical M.O., the team officially signed Phil Maton to a two-year, $14.5 million deal earlier in the week and was reportedly interested in signing another high-leverage reliever in Ryan Helsley.
However, fortunately for the Milwaukee Brewers, both Cease and Helsley have agreed to contracts with teams other than the Cubs, forcing Chicago’s front office to pursue their second or third options this offseason.
Cubs miss out on Dylan Cease and Ryan Helsley as each agree to contracts with AL East teams
Just before Thanksgiving arrived, one of the Cubs’ top offseason targets was taken off the board. The defending AL Champion Toronto Blue Jays reportedly agreed to a deal with Dylan Cease that will pay him $210 million over the next seven seasons. It’s not only a huge splash for the Blue Jays that signals their commitment to building upon their memorable 2025 season, but it also sets a high price for starting pitching as the rest of the league looks to bolster their rotations.
Then, on Saturday evening, the Baltimore Orioles agreed to a two-year, $28 million deal with Ryan Helsley, just days after Patrick Mooney of The Athletic reported that Chicago was interested in signing the former St. Louis Cardinals closer. Once again, the Cubs found themselves outbid by an organization that was willing to offer what appears to be a slight overpay in order to bring in a top-tier arm.
While plenty of starting and relief pitchers still exist on the free agent market, there also exist plenty of teams in need of reinforcements to their pitching staffs. Chicago, still in search of a frontline starter and a high-leverage reliever, may have to get more creative with their signings now that two of the biggest names are off the board. In addition, as previously alluded to, teams looking to add pitchers this offseason will now be forced to match the high salaries that both Cease and Helsley commanded. That combination could lead to the Cubs making an ill-advised signing in a moment of desperation.
