Jameson Taillon New York Yankees
Jasen Vinlove-USA TODAY Sports

Jameson Taillon was good enough in two years with the Yankees that he should command a fair bit of interest in free agency. If you were to ask the veteran righty, he already has some ideas.

Sports Illustrated reported last month that Taillon would “love” to re-sign with the Yankees, who acquired him from the Pirates before the 2021 season. In 2022, he went 14-5 with a 3.91 ERA in 32 starts.

There’s certainly room for the Yankees to consider Taillon. The team has an opening in its starting rotation, though the Yankees have in-house options. This could be Clarke Schmidt’s chance to finally take the plunge and be an important starting pitcher like he was in the minors.

But with so much uncertainty surrounding Aaron Judge’s free agency, the Yankees must also prioritize pitching to stay competitive. In such a case, keeping Jameson Taillon makes much more sense. The Yankees’ pitching ranked third in baseball with a 3.30 ERA, and Taillon’s track record trumps Schmidt’s upside or any other prospects in the mix.

Pros: Look at it this way. Taillon turns 31 later this month and pitched pretty well considering he’s had Tommy John surgery twice. He posted an elite 1.6 walks per nine innings (BB/9) and his fastball spin was in the 85th percentile, per Statcast. Taillon is also best friends with Yankees ace and former Pirates teammate Gerrit Cole. This, in turn, helps the pitching staff buy into coach Matt Blake’s philosophy.

Retaining Taillon also makes sense from a money standpoint. He only made $5.8 million last season and didn’t put up numbers commanding of $20 million a year. Whether it’s Brian Cashman or someone else negotiating, there’s a path to Jameson Taillon staying with the Yankees.

Cons: Meanwhile, the downside to the Yankees’ re-signing him is two-fold. The first and obvious reason is New York’s pitching depth. Clarke Schmidt should be the No. 5 starter, but Domingo German and Deivi Garcia could also be in the mix. Yet, none of these three have a track record as proven as Taillon’s.

There’s also the strong possibility that Jameson Taillon does indeed leave in free agency. Justin Verlander and Jacob deGrom are the two biggest arms on the market who will command $40 million a year. The rest of the field, by contrast, is mostly aging and average arms. It’s completely possible that Taillon could be overpaid by another team if the Yankees’ hold firm on their analytics-driven offer.

Verdict: But at the end of the day, it makes more sense for the Yankees to keep Jameson Taillon. He’s a solid enough arm to fill the back of the rotation and give New York a few more years to develop a homegrown arm. Clarke Schmidt just looks better suited as a middle reliever and his 4.95 starter ERA sticks out, even in a small sample size. He’ll fare best in the bullpen while Taillon balances the rotation.

Prediction: Jameson Taillon re-signs with Yankees for four years, $55 million.

Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.