Predicting the Cubs' strongest trade targets that learn from Jed Hoyer's past mistakes

It's entirely possible that the Chicago Cubs will move mostly through free agency before the MLB lockout is in effect on December 2, but this is a front office that loves to explore the trade market. In an ideal world, one could suggest the Cubs would prefer a majority of their heavy lifting through the trade market, leaving open their financial resources for adding an established outfielder to their starting lineup for the 2027 season.

Using the Edward Cabrera deal as reference, when the Cubs have looked to the trade market for pitching, the hope has been they can find someone who is not only under control, but somewhat of an unfinished product. They idea being that it's cheaper than trading for an ace who is under control for multiple seasons, and cheaper than going to the top of the market in free agency. Clearly, there's risk in that approach, and the Cubs found that out during the 2026 season with Cabrera's struggles.

There's also the the one time they traded for one year of a superstar bat in Kyle Tucker. The trade, for what it was meant to provide, worked. Tucker's presence helped the Cubs reach the playoffs in 2025, but, in the end, it felt like that type of trade would be the exception and not the rule for Jed Hoyer's front office moving forward.

Ranking the Cubs' trade targets from pipe-dream targets to realistic options and everything in-between

On some level, it would be fair to assume that Hoyer will have both of those trades in mind for any deal he tries to make this offseason. Rather than a work-in-progress like Cabrera, perhaps the Cubs target a starting pitcher that would arrive with established expectations. It's also likely that the Cubs would be in the market for a one-year of a veteran outfielder, but likely not the type of trade they made with the Astros for Tucker.

Similar to our free agency guide, we are going to group targets together based on high likely a trade may be, and some targets who would be a dream for the Cubs but may not happen for a variety of reasons.

The Cubs would love to trade for these players, but it's a pipe-dream

• Reid Detmers
• Logan Webb
• Jacob deGrom

Reid Detmers is the one who got away at the trade deadline. Since then, there's been varying reports debating just how close the Cubs were to adding him from a Los Angeles Angels. Since the deadline, Detmers went on to post an ERA of 1.95 while striking out over 29% of the hitters he faced during his final 10 starts of the season. More reason for the Cubs to be in love with him. The problem is the Angels are stuck in place until Stan Kroenke's purchase is approved, and with John Mozeliak already confirming he will be out once the new regime is in place, it's hard to imagine he makes a deal to the level of moving Detmers.

Logan Webb is always mentioned in this type of thing. Despite the San Francisco Giants giving no indication that Webb will be shopped or will be on the move, that doesn't stop teams from calling. It was a down year for Webb in 2026, posting an ERA of 4.31, but his underlying metrics were in line with his career averages. He also kep the ball on the ground over 50% of the time. He's an ace and would be a natural fit at the top of the Cubs' rotation. The problem is there's just belief that the Giants will move him.

Dating back to the trade deadline, it's seemed like the Texas Rangers have had a desire to trade Jacob deGrom. The early word is that they will try again this offseason. The goal would be finding a team to take on deGrom's remaining money, and while the Cubs certainly could, there's the reality of deGrom having a no-trade clause. The indication is that he has no desire of leaving Texas.

These trade targets should all be within reach of the Cubs this offseason

• George Kirby
• Emerson Hancock
• Joe Ryan
• Drew Rasmussen
• Steven Kwan

More times than not, offseason trades can be traced back to pursuits a team made at the deadline. In this case, it would be fair to wonder if the Cubs give the Mariners a call. There's an expectation that the Mariners will reset their roster this offseason, and they could trade from their surplus of pitching. George Kirby and Emerson Hancock were two pitchers the Cubs had interest in over the summer, and they both likely remain on the team's radar.

There was an offseason for the Minnesota Twins to finally trade Joe Ryan, it would be this one. He's a free agent after the 2027 season, and his trade value won't be any higher than what it currently is. Ryan would be the clear ace that the Cubs have lacked over the last two years, and he struck out over 25% of the hitters he faced last year. His career mark is over 27%.

Drew Rasmussen is set to earn $20 million in 2027, and that's led to speculation that the Tampa Bay Rays could look to trade him this offseason. If so, he's someone the Cubs need to have on their radar. Since making his debut in 2020, he's only had one season where his ERA was over 3.00. Last year, he posted an ERA of 2.67 across 30 starts. He also has an ideal mix of missing bats, 26% strikeout rate last year, and keeping the ball on the ground, career ground-ball rate of 47.5%. That is the exact type of pitcher the Cubs need at the top of their rotation.

The only position player mentioned, Steven Kwan is an ideal fit for the Cubs' outfield. He doesn't have the power that the Cubs are losing in Seiya Suzuki and Ian Happ, but he's a plus fielder with speed and a contact-oriented approach. The Cleveland Guardians have suggested that Kwan will be on their roster in 2027, but with his free agency looming, that feels like posturing.

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