A Jameson Taillon Trade Feels Almost Inevitable, in a Good Way

[Matthew Trueblood]

It's hard to survey the number and specific identity of the teams who have reportedly shown interest in the Cubs' veteran righthander without coming to the conclusion that the wheels of a deal are in motion.

Image courtesy of © Matt Marton-USA TODAY Sports

This week has seen an absolute torrent of Jameson Taillon trade rumors. It might be easier to name teams who haven't been linked to him, but for the sake of clarity, let's just list those who have: the Houston Astros, New York Yankees, Boston Red Sox, and Baltimore Orioles. When I wrote about Taillon's trade value earlier this month, I mentioned the Mets and Guardians, who haven't yet appeared as rumored destinations, but they, too, remain solid fits.

All these teams make sense as fits for Taillon, for various reasons. The Orioles just need some depth and reinforcement in their rotation, as they navigate a season in which they've lost two starters to Tommy John surgery but still look like locks to reach the postseason. The Yankees have a history with Taillon, and as Cubs fans know by now, he's an agreeable, fine presence for any clubhouse, so it's no shock that a former employer would be interested in having him back. We can safely assume that Taillon is familiar to (and well-liked by) Red Sox chief executive Craig Breslow, since he was heading up the Cubs' pitching department when the team signed Taillon two offseasons ago. Houston, like Baltimore, needs healthy and reliable arms.

Of course, those teams all also share an important characteristic: they have big budgets and room to spend, this year and next. That makes them interesting trade partners for a Taillon deal, because if the Cubs do move him, they could look to absorb a portion of his remaining salary (roughly $6 million for the balance of 2024, and $18 million in each of the next two campaigns) to improve the talent they get in return for him. Doing so would not help them replace Taillon this winter via free agency, as they'd surely need to do, but they should have plenty of room in their own budget to do that, anyway. A trade with a rich team ready to take on Taillon's full freight would mean one with a less exciting young player or two coming back.

Then again, each of these clubs has some reason to let the Cubs help them financially and give up a little bit of extra talent, in exchange. The Astros are very close to crossing the second luxury-tax threshold for this season, and they face some tough decisions about Alex Bregman, Framber Valdez, and Kyle Tucker in the coming months and years. Boston, Baltimore, and New York all have ownership groups whose willingness to spend seems to fluctuate unpredictably, but with the Yankee payroll well over $300 million for this year as it is, they'll pay heavy taxes on any further money added, and that's going to be true for several years to come.

Taillon still has two and a half years left on his contract, but the way he's pitched over the last calendar year (32 starts, 178 innings pitched, a 3.34 ERA, a .666 opponent OPS), he has tremendous excess value, anyway. The Cubs should only trade him if they can get both some salary flexibility and significant young talent in the deal, but that suddenly looks very plausible. It would be a mild surprise, at this point, if he's not dealt by Tuesday evening. He can help some new team in as many as three pushes to the postseason, but hopefully, a trade can also net the Cubs something that helps them in just as many, down the road a year or two.

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