The Cubs may spend plenty of this offseason in free agency before the MLB lockout hits on December 2, but this front office has never been shy about working the trade market. And if Jed Hoyer is going to swing a deal, the recent history is pretty clear: Chicago would rather land a pitcher with control and upside than gamble on another unfinished project like Edward Cabrera, while also keeping an eye out for a veteran bat if the right one-year fit shows up.
That Cabrera trade is the cautionary tale here. The Cubs hoped they were getting a cheaper path to pitching help - someone under control, still developing, and less expensive than chasing an ace in trade or free agency.
The idea made sense on paper. The 2026 season showed the downside.
On the other end of the spectrum sits Kyle Tucker, the one-year superstar bat who did exactly what Chicago wanted and helped the Cubs reach the playoffs in 2025. The lesson from that deal, though, seems to be that it was the exception, not the model.
So the Cubs’ trade board this winter falls into a few different buckets, starting with the names that would be dream fits but probably stay out of reach.
Reid Detmers is the obvious “what if” from the deadline. Reports have varied on how close the Cubs actually came to getting him from the Los Angeles Angels, but there’s no question why he still makes sense.
After the deadline, Detmers put up a 1.95 ERA and struck out more than 29% of the hitters he faced over his final 10 starts. The problem is that the Angels are stuck in place until Stan Kroenke’s purchase is approved, and with John Mozeliak already saying he’ll be out once the new regime arrives, it’s hard to see that front office making a move of that size.
Logan Webb is another name that always gets floated in this kind of conversation. The San Francisco Giants haven’t given any indication that he’s available, but that never stops teams from asking.
Webb had a down 2026 by his standards with a 4.31 ERA, though the underlying numbers matched his career norms and he kept the ball on the ground more than 50% of the time. He’d fit neatly at the top of the Cubs’ rotation.
The issue is simple: there’s no real belief the Giants will move him.
Jacob deGrom has been part of the rumor mill too, with the Texas Rangers expected to revisit trade talks this offseason after a deadline push. The goal would be to move his remaining money, and Chicago could certainly absorb it. But deGrom has a no-trade clause, and the indication is that he has no desire to leave Texas.
A more realistic path may be to circle back on pitching targets the Cubs already checked on over the summer. The Seattle Mariners are expected to reset their roster, and that could mean dealing from their pitching depth. George Kirby and Emerson Hancock were both on the Cubs’ radar at the deadline, and both figures remain in the mix if Seattle listens.
Joe Ryan also stands out as a name worth watching. If the Minnesota Twins are going to move him, this offseason would be the time.
He’s under control through the 2027 season, and his value may never be higher. Ryan would give the Cubs the kind of ace they’ve been missing for the last two years, and he struck out more than 25% of hitters last season.
His career strikeout rate is over 27%.
Drew Rasmussen is another arm that fits the profile Chicago should want. He’s set to earn $20 million in 2027, which is why there’s speculation the Tampa Bay Rays could shop him.
Since debuting in 2020, he’s had only one season with an ERA above 3.00. Last year he posted a 2.67 ERA in 30 starts, paired with a 26% strikeout rate and a career ground-ball rate of 47.5%.
That’s the kind of combination the Cubs need near the top of the rotation.
Steven Kwan is the lone position player in the mix, and he checks a lot of boxes for the Cubs’ outfield. He won’t replace the power Chicago is losing in Seiya Suzuki and Ian Happ, but he brings speed, contact, and strong defense. The Cleveland Guardians have said Kwan will be on their roster in 2027, though with free agency getting closer, that reads more like posturing than certainty.
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Alex Bregman Just Gave Cubs Fans Real Reason To Believe
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What matters most for the Cubs is how he closed the season, because the late surge did more than clean up the numbers. It gave the lineup a more reliable tone heading into 2027 and offered a reminder that the signing was about more than name value, with Bregman looking like a player who can anchor the offense when it matters most. [Read more 🡒]
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The timing adds another layer of pressure. Because the NPB and MLB agreed to a modified posting window this offseason due to a pending lockout, teams have only 30 days to get a deal done, which compresses the process and rewards clubs ready to move quickly. The Cubs are viewed as a potential suitor, and if they want to stay in the conversation, they may need to act before the market tightens and the competition gets even more serious. [Read more 🡒]
Cubs May Finally Have A Real Shot At Freddy Peralta
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What makes him especially intriguing is the way his game has evolved, with his recent success giving clubs reason to believe there is still another level to tap into. The fit is obvious enough that speculation has already started to build around where he could land, but the real question for the Cubs is whether they are willing to move quickly enough to turn interest into a serious pursuit. [Read more 🡒]