The Chicago Cubs walk into the offseason with some pressing issues facing them. The biggest issue, perhaps, is related to pitching.
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To sum it up succinctly, the Cubs are going to need a lot of help in the pitching department. There will be a lot of holes to fill and a lot of reinforcement needed to ensure protection from regression among those who most likely overperformed during the 2024 season.
The bullpen, for example, will need an almost complete overhaul as six of the eight relievers on the NLDS roster may be gone via free agency. This is working under the fair assumption, of course, that the team won’t be ponying up the money to keep bullpen standouts Brad Keller, Drew Pomeranz, and Caleb Thielbar.
The return of Justin Steele to the starting rotation will be a big deal. However, this is assuming that Steele stays healthy and re-finds his groove. The Cubs will also be counting on Matthew Boyd and Cade Horton to not only stay healthy, but to also avoid regression from a tremendous– and perhaps a bit unrealistic– 2025. If all doesn’t go according to plan, there will be a lot of uncertainty in the Cubs rotation. To help mitigate the doubts, they will need to add some more depth this offseason.
With the front office seemingly focused on moving young talent into positions of roster prominence in 2026, it seems unlikely that they would trade a Ballesteros, Caissie, or Wiggins for a high-end impact arm.
Chicago Cubs will dig into the free agent market
Jan 12, 2024; Chicago, IL, USA; Chicago Cubs president of baseball operations Jed Hoyer talks to the media after introducing pitcher Shota Imanaga (not pictured) during a press conference at Loews Chicago Hotel. Mandatory Credit: Kamil Krzaczynski-Imagn Images
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So, any roster reinforcement will have to come via free agency.
And that’s where the Cubs will likely be slipping into their same old bad buying habits.
Rather than go out and flex their major market/major revenue muscles with big, bold purchases, Chicago works around the fringes, looking for bargain buys and cheap rehabilitation projects. This “roll the dice,” mindset has paid dividends on several occasions, notably on Boyd, Keller, Pomeranz, and Thielbar this past season. It could also be argued, however, that it’s kept the team from acquiring any true elite-level impact players and, therefore, put a cap on just how far the team can go.
Early Cubs free agent rumors for 2026 completely fit into the team’s modus operandi and budget-minded ways.
Free agent rumors ring true
Sep 12, 2025; New York City, New York, USA; New York Mets relief pitcher Ryan Helsley (56) pitches against the Texas Rangers during the ninth inning at Citi Field. Mandatory Credit: Brad Penner-Imagn Images
Several media outlets have tied former St. Louis Cardinals closer Ryan Helsley to the Cubs, something which would’ve had Cubs fans salivating back last season, before the 31-year-old was dealt to the Mets at the trade deadline. In New York, in the heat of a failing pennant drive, Helsley was absolutely awful with a 7.20 ERA and poor performance across the board.
His total disintegration at the end of 2025 will reduce his free agent market value, despite a career’s worth of previous success, and maybe put him right into the Cubs’ comfort zone when it comes to a possible short-term contract for a manageable amount of money.
Similarly, Shane Bieber will become a free agent after he tries to help the Toronto Blue Jays get past the Los Angeles Dodgers in the World Series. As recently as the All-Star break, though, it was no sure thing that the two-time All-Star and former Cy Young winner would even be able to pitch again at the major league level as he recovered from UCL surgery in 2024.
The Blue Jays gambled on his ability to come back and acquired him from the Cleveland Guardians at the trade deadline, as he was still rehabbing from his injuries. Bieber has been solid since his return, posting a 3.57 ERA in seven regular season starts and a 4.38 ERA in three postseason appearances.
His recent-recovery status will make teams shy away from offering him a lucrative multi-year contract—something which would be perfect for the Cubs. Jed Hoyer and company could swoop in and sign the 30-year-old to a one-year deal where he could reestablish his status as an elite-arm and then head back into free agency in pursuit of monster money.
Buzz surrounding former Cub Anthony Kay also fits into the Cubs’ free agent mindset.
The left-handed Kay has found incredible success in Japan these past two years after a disappointing 5-year MLB run. His 1.74 ERA for the Yokohama DeNA BayStars in 2025 was a franchise record and has reportedly pushed him towards a return to the US.
The 30-year-old has worked as a starter in Japan after reliever status through his MLB career. A one-year deal to showcase his worth as a starter/swing man before pursuing bigger contracts is probably the plan. And the Cubs could be right there to snatch up the ground ball-heavy southpaw at a reasonable price for a single season of service.
The need to change course
MLB: Cleveland Guardians at Chicago Cubs Jul 3, 2025; Chicago, Illinois, USA; Chicago Cubs president of baseball operations Jed Hoyer speaks before a baseball game between the Chicago Cubs and Cleveland Guardians at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images
Picking up Helsley, Bieber, and/or Kay would not be bad decisions. Picking them up for a relative song with minimal long-term risk would also not be a bad thing. The problem is that the Cubs are always cutting these types of deals, something which comes at the expense of long-term stability and their ability to attract true elite-level impact talent to the team.
The Cubs need to start investing in talent acquisition if they’re truly serious about establishing a winning tradition in Chicago. They need to save the bargain bin shopping for the ancillary pieces, but step up when it comes to main stage players.
Chicago Cubs are going young, like it or not
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