Trading Jameson Taillon Might Be Key to Successful Winter Meetings

Though the Cubs have yet to sign anybody who’s a noted difference maker — apologies to Matthew Boyd — they’ve added four relievers in typical Jed Hoyer style. Nobody had Rob Zastryzny, Eli Morgan, Phil Bickford, or Brooks Kriske on their free-agent bingo card, but those types of transactions are how Hoyer usually steals a win or two. Still, the Cubs are at the forefront of several trade rumors. Cody Bellinger and Nico Hoerner have been linked to a few teams in outbound moves, and yesterday Hoyer appeared close to pulling off a three-way trade to acquire Garrett Crochet.

Nothing’s happened yet, but Chicago’s top executive has laid the foundation for a very busy Winter Meetings slate that informally commences Sunday evening. Joel Sherman of the NY Post suggests the Yankees should acquire Bellinger even if they retain Juan Soto. Indeed, New York is one of three teams that has already kicked the tires on the outfielder/first baseman. He also said that Hoyer was trying to move Bellinger (due $27.5 million in 2025 with a $25 million player option in 2026 or $5 million buyout) and/or Seiya Suzuki (2/$36 million) “to reallocate that money elsewhere.” You may as well add Jameson Taillon to that list if those rumors are true. Suzuki has a no-trade clause, by the way.

Taillon could be this year’s sleight-of-hand transaction by Hoyer and perhaps the key to a successful hot stove season. While most analysts are focused on Bellinger, Hoerner, and perhaps Suzuki, the president of baseball operations could be looking to move the veteran starter. If he were a free agent, Taillon would rank somewhere between Max Fried and Jack Flaherty. The hole left in Chicago’s rotation could be filled by Crochet, which makes a lot more sense given yesterday’s rumors. Hoyer said earlier this winter that he’d have to get creative to add to the roster, and moving Bellinger, Hoerner, and Taillon would give him an extra $57 million in payroll pocket change. It’s almost enough to ponder the merits of signing Soto.

Soto isn’t coming to Chicago, but Owen Caissie, Kevin Alcántara, and Alexander Canario are nearly ready to replace Bellinger. While a potential move may feel like a salary dump to some, that’s not necessarily true. Harrison Bader is the top centerfielder available in free agency, so a market for Bellinger exists. Lofty salary aside, the beloved Cubs outfielder could be a core piece for any team that whiffs on Soto, though Bellinger’s contract is tough to swallow due to next year’s player option.

Taillon has been a trade candidate going back to last winter and he makes sense even for small-market teams whose competitive windows are wide open. That could include the Orioles and Royals, but you could add the Red Sox and Giants to the list of interested parties as well. Both clubs are always looking for pitching and Taillon would provide stability to both rotations. However, the Cubs can’t trade the veteran righty without a replacement. Jordan Wicks or Cade Horton might do, but either or both could be part of a Crochet trade. That’s okay, because Ben Brown proved in 2024 he could be a dominant starter. Imagine a rotation of Crochet, Justin Steele, Shota Imanaga, Boyd, and Brown. Javier Assad is a perfectly fine swingman and fill-in for the oft-injured Boyd. That’s also a top three capable of winning any playoff series.

Hoerner is expendable because Matt Shaw is ready. That’s the easy move but it’s also shortsighted. The Cubs are stronger up the middle than most teams because of Hoerner, Dansby Swanson, and Pete Crow-Armstrong. Trading Isaac Paredes, who makes a lot of sense for the Mariners, is the more prudent option. Shaw can play third, get some big league experience, and move over to second when Cam Smith is ready. The Cubs can keep Hoerner if they move Bellinger and Taillon.

That leaves Suzuki, who would undoubtedly return to right field if Bellinger is traded. Chicago will sacrifice some defense, but the team is still much-improved. That’s a lot of moving parts just to get Crochet while adding Shaw to the lineup. Hoyer is seeking bullpen additions, a top-of-rotation starter, and a catcher. All three might be in his grasp by trading Bellinger and Taillon while acquiring Crochet. He’d also have the financial and prospect flexibility to make bolder moves if he chooses.

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