Yankees might’ve created Jameson Taillon’s massive market

Jul 10, 2022; Boston, Massachusetts, USA; New York Yankees starting pitcher Jameson Taillon (50) reacts during the second inning against the Boston Red Sox at Fenway Park. Mandatory Credit: Paul Rutherford-USA TODAY Sports
Jul 10, 2022; Boston, Massachusetts, USA; New York Yankees starting pitcher Jameson Taillon (50) reacts during the second inning against the Boston Red Sox at Fenway Park. Mandatory Credit: Paul Rutherford-USA TODAY Sports /
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It’s easy to call the Yankees’ decision not to give the ~$19 million qualifying offer to Jameson Taillon a front office mistake now that we all know how robust the right-hander’s free agent market has become at the Winter Meetings.

In reality, though, this is likely a Gift of the Magi situation. Taillon would’ve had suitors regardless of the Yankees’ behavior, but they likely wouldn’t have been quite as fervent if he came with a draft pick attached. Conversely, the right-hander probably would’ve taken a three-year deal over the Yankees’ expensive theoretical one-year offering, but if he’d accepted their significant raise, all Aaron Judge/free agency proceedings would’ve come with a bloated asterisk; namely, a $19.65 commitment to a player they were happy to otherwise move on from.

Thanks in part to the Yankees declining to drape Taillon in a draft pick blanket and a “warning” label, teams have been all over the right-hander at the Winter Meetings thus far.

As of Monday afternoon, the Mets, Phillies, Cubs and Orioles seem to be in the pool battling for his services. Of those teams, New York almost certainly has higher ambitions, and would be counting on Taillon to fill the Chris Bassitt/Taijuan Walker role, while the Orioles are looking for a high-end complement to Kyle Gibson, who signed over the weekend.

It’s possible that the O’s would be out entirely if Taillon came with a draft pick, while the Cubs would be cautious, too.

Did Yankees create Jameson Taillon’s robust free agency market by ditching Qualifying Offer?

The Mets, Phillies and Cubbies all currently plan to chase free agents in a tier above Taillon (Justin Verlander, Xander Bogaerts, Dansby Swanson, Trea Turner), so they all likely entered the offseason planning to lose a draft pick on somebody regardless. They would’ve likely been perfectly alright further decimating their pile of picks for Taillon — or maybe they would’ve pivoted, rather than thinning out their crop any further?

The Orioles almost certainly would’ve ducked out of the fast-developing Taillon market if they had to give up a top-shelf pick. Instead, they might be the on-the-verge-of-contention team that actually pays him something close to $70 million for four years. That’s a massive step up from what seemed realistic after Tyler Anderson, with the Qualifying Offer attached, settled for much less with the Angels.

When Brian Cashman’s last year is assessed at every stop, not offering Taillon the QO feels like a mistake akin to not extending Judge before the season or taking on Josh Donaldson’s money. In reality, this one’s probably a “Chicken or the Egg?” situation.