Chicago Cubs fans can cross off one big name from their holiday wish list. Yesterday, it was announced that the Toronto Blue Jays had signed hard-throwing free agent righty (and former Cubs prospect) Dylan Cease to a 7-year, $210 million contract (with just under $30 million of that money coming via deferred payment).
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The strikeout specialist was a rumored target of the Cubs throughout the early offseason and would’ve fit in the rotation nicely as a much-needed power pitcher among general finesse starters.
The Cubs could’ve made the same deal as the Blue Jays. The money is there and the books are almost entirely clean after this upcoming season. However, the Ricketts family ownership, for some reason, doesn’t entertain deals with deferred money, despite it being an increasingly attractive contract stipulation for players looking for tax breaks and money beyond their playing days. Because of this steadfast refusal to work with these kinds of arrangement, the Cubs will find it more and more difficult to land big-ticket free agents.
That is assuming, of course, that the Cubs will EVER be in serious pursuit of a big-ticket free agent.
Chicago Cubs, not likely to be big spenders after all
Chicago Cubs Chairman Tom Ricketts (R) smiles next to Chicago Cubs President of baseball operations Jed Hoyer (L) before a baseball game between the Chicago Cubs and Cincinnati Reds at Wrigley Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images
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Losing out on Cease is really not much a surprise, but this first major free agent domino to fall may serve as the first reality check of many more to come for the Cubs and their fans. Despite all the rumors and the targeted leaks about the team being serious buyers this winter, it’s quite likely that they won’t be spenders at all.
Following that line of thought, a recent poll of anonymous MLB execs for ESPN reveals that most don’t fancy the Cubs’ chances of landing one of the big free agents at all.
Aside from minor acquisitions and the usual reclamation projects Cubs president Jed Hoyer loves to pick up on the cheap, there might be zero dipping of the proverbial big toe into the deep end of the 2026 free agent talent pool.
There’s buzz that Cubs ownership is legitimately spooked about the impending labor dispute and likely 2027 lockout. It’s probably not a coincidence that the team’s payroll has no contracts extending beyond 2026, other than Dansby Swanson and recently acquired reliever Phil Maton. It would be a real stretch to assume the Cubs would take on a big-money 5-7 year contract right now, with so much uncertainty tickling the brain stems of an already overly-cautious ownership.
Trade over free agency
Feb 20, 2025; Phoenix, Arizona, USA; Chicago Cubs outfielder Kevin Alcantara against the Los Angeles Dodgers during a spring training game at Camelback Ranch-Glendale. Mandatory Credit: Mark J. Rebilas-Imagn Images
But that doesn’t mean there won’t be a major acquisition this winter. It’s just that the impact pickup will have to come via trade.
Actually, in this environment and with the uncertainty of the labor dispute on everyone’s mind, the Cubs may find an easier path to making a major trade. Teams looking to unload talent may opt to deal this offseason rather than wait for the trade deadline and what surely will be a diminished return due to the possible lockout.
Conveniently enough, the Cubs just happen to be loaded with young assets who either have their paths blocked at the major league level or are simply out of major league options.
Outfielder Kevin Alcantara is unlucky enough to fall into both of the above categories. With no options remaining, the Cubs will have to keep him in the majors if they bring him up or lose him entirely if they decide to later demote him. Lefty pitcher Jordan Wicks has fallen out of favor in Chicago and has reportedly been dangled as a trade piece. Second baseman James Triantos’ star has fallen a bit, but his path to the majors is blocked by Nico Hoerner, anyway. Jonathon Long was a revelation in 2025 and won Cubs minor league player of the year honors, but he’s a first baseman and, barring injury or odd decline, Michael Busch isn’t moving from first. It’s still even possible that Owen Caissie and Moises Ballesteros– two prospects tabbed to play big roles on the major league squad in 2026– could be moved under the right circumstances.
Trade targets
MLB: Philadelphia Phillies at Miami Marlins Jun 19, 2025; Miami, Florida, USA; Miami Marlins starting pitcher Edward Cabrera (27) delivers a pitch against the Philadelphia Phillies during the first inning at loanDepot Park. Mandatory Credit: Sam Navarro-Imagn Images
And who could the Cubs trade FOR?
27-year-old right-handed starter Edward Cabrera of the Miami Marlins has been mentioned a lot. The feeling that Cabrera has turned the right corner on his development could motor the Cubs’ pursuit. But his team-friendly contract, which extends through 2028, could cinch the deal. The Cubs might be willing to spend major trade capital in acquiring him.
There are other names out there, beyond Cabrera. The Twins’ Joe Ryan, the Nationals’ Mackenzie Gore, the Pirates’ Mitch Keller, and the Marlins’ Sandy Alcantara all come to mind. All give Chicago team-controlled years and front-of-rotation potential.
The question will be whether the Cubs will be as stingy in handling their trade-attractive prospects as they are with their money.
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