The Cubs went after Kevin Gausman at the deadline for a reason: they wanted a proven arm with postseason miles on him, someone who had already lived through October pressure and could steady a rotation that needed help. Instead, Chicago got only a brief look before the season ended in disappointment and the questions started piling up.
Gausman’s Cubs stint was supposed to be a bridge to something bigger. He arrived in the final year of the five-year, $110 million deal he spent entirely with the Blue Jays, where he had become a fan favorite and a key part of Toronto’s run to the World Series during the 2025 campaign.
Chicago made the move hoping that experience would matter in a short postseason push. He wound up appearing in just one playoff game.
That’s part of why the trade already feels shaky. The Cubs lost the top Wild Card spot, then dropped two games to the San Diego Padres on the road, failing to reach the NLDS. Now the offseason brings even more uncertainty, especially on a pitching staff that could look very different next year.
Clay Holmes, Shota Imanaga, and possibly Matthew Boyd are all set to hit free agency, which opens the door for plenty of turnover in the rotation. That has naturally led to some speculation about whether Chicago might try to keep one of its veteran additions. Gausman fits that idea on paper: swing-and-miss stuff, playoff experience, and the kind of presence a win-now club likes to have around.
But the reunion talk is already gaining traction elsewhere. Mitch Bannon of The Athletic reported that it’s unclear whether Gausman will continue his MLB career, but if he does, it is "likely" that he would reunite with the Blue Jays this winter.
That doesn’t shut the door on the Cubs. They liked Gausman enough to trade for him, and it’s possible they would try to bring him back.
But Toronto clearly has its own pull. Gausman has deep roots there, and that could matter more than anything Chicago can offer.
The performance side of the equation also matters. Gausman had some strong outings, but his regular season ended with a 4.83 ERA over nine starts.
Opponents put plenty of contact on him, and they did damage with power late in the year. That makes it easier to see why Chicago might decide not to make him a priority.
The bigger issue for the Cubs is the price they paid. Jed Hoyer gave up two Top 20 prospects, including outfielder Brett Bateman. Bateman reached the Blue Jays’ big-league roster quickly and finished the year at .329 with an .826 OPS in 41 games, along with three stolen bases.
That leaves open an awkward possibility for Chicago: Toronto could start 2027 with Gausman back in the rotation and Bateman in the everyday lineup. Even if that stops short of a true fleece, it would still be a rough look after Gausman logged only ten total games for the Cubs.
And there’s another layer that could make the whole thing sting even more. Bannon reported in the same piece that Toronto is expected to pursue Cubs slugger Seiya Suzuki in free agency later this winter. If the Blue Jays land him too, the aftermath of this deadline deal gets a lot uglier.
The Cubs were justified in swinging big when they were one of the hottest teams in baseball. That’s the part of the job that comes with being aggressive: you have to show your fan base you’re willing to push in. But moves like this don’t always cash in, and this one already has the feel of a trade Chicago may regret very soon.
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