What would an extension for James Paxton look like?

Earlier in the offseason, I implored the Yankees to sign Gerrit Cole based on the risk their starting rotation contained going forward. Signing Cole was a slam dunk for a number of reasons, but chief among them, to me, was the fact that the Yankees had Luis Severino and little else locked down past 2020.

Signing Cole gives the Yankees a dynamite one-two punch for at least the next four years, and a potential ace for much of the next decade. Some of the questions I raised about the rotation’s future depth, however, remain even with Cole on board.

James Paxton, Masahiro Tanaka, and J.A. Happ all stand to become free agents after next season, while the latter may not make it to Opening Day on the Yankees’ roster. Cole, and Severino, ensure the team’s rotation will have tons of upside in 2021 and beyond, but the pickings are still slim outside of the top two.

Deivi Garcia could change the complexion of the rotation going forward. Perhaps Jordan Montgomery reestablishes himself as a quality mid-rotation starter next season. By 2021, one of the Yankees’ fistful of fire-balling prospects, such as Clarke Schmidt, Albert Abreu, or Luis Gil, among many others, could have emerged as a legitimate starting option at the major-league level.

All of those are question marks. If the Yankees want to provide themselves some level of real security with regards to their future rotation, the best option they have right now is to try to extend one of their impending free agents. They should look no further than the Big Maple.

Paxton is a prime extension candidate, entering his age-31 season and his final year of arbitration. The left-hander is represented by Scott Boras, who prefers to let his clients reach free agency and test the free market, so the Yankees would have put together a strong offer reflective of Paxton’s value to force him to consider.

What would such an offer look like? Unfortunately, we don’t have many recent examples of starters one year out from free agency who signed extensions. The best parallel we can find might be Danny Duffy, who signed a five-year extension ahead of the 2017 season. Duffy, also a left-hander, posted a 123 ERA+ across 465.2 innings in the three years before signing his extension. Paxton has posted a 119 ERA+ across 447 innings the past three seasons.

Duffy signed away his 2018-2021 seasons for nearly $60 million. If we account for rising salaries over the past three years, Paxton could ask for over $70 million over four years from the Yankees. In light of recent free-agent signings, that feels a little light.

Perhaps, then, looking to the free-agent market will give us a better idea of what Paxton could fetch. Zack Wheeler provides a useful analogue. Like Paxton, Wheeler has long had excellent stuff but merely good results. Wheeler can dial it up towards 100 mph and has a 3.37 FIP over the past two years, but only a 107 ERA+. Paxton has posted a 3.54 FIP and a 112 ERA+ over that span.

Wheeler locked down a five-year, $118-million contract from the Phillies, in part because his stuff suggests potential beyond the numbers he’s managed with the Mets. Signing Paxton to an extension would likely follow a similar template. Paxton’s run prevention numbers don’t entirely match up with his top-flight stuff, but he showed flashes of his ceiling down the stretch last season. As the Phillies did with Wheeler, the Yankees would probably have to up their offer because of Paxton’s obvious upside.

Wheeler has age on his side, though, as he’s a year younger than Paxton. That brings us to the final two comps I want to provide for Paxton; Madison Bumgarner and Hyun-jin Ryu. The former took home $85 million over five years from the Diamonbacks, while the latter just signed for $80 million across four years from the Blue Jyas. This pair might get us closest to what Paxton could require in an extension.

Ryu is older than Paxton and has stellar run prevention figures over the past two years, while Bumgarner is a year younger than Paxton and has a longer track record, but less upside. Both ended up in similar places in terms of contractual details. At this moment, Paxton probably profiles in their tier. Paxton isn’t young enough to get the big deal Wheeler secured from Philadelphia, nor is he good enough to sign a mega-deal like Stephen Strasburg.

So, a four- or five-year deal in the $20-million range seems like it would be a legitimate offer for someone of Paxton’s age, talent, and track record. If Paxton is interested in such a deal, the Yankees should pounce. Paxton has established a baseline of a roughly three-win pitcher, even as he’s frustrated at times and failed to reach his ultimate upside. The downside of such an extension involves Paxton never improving on that baseline. The upside entails Paxton harnessing his potential into a few ace-caliber seasons.

Given how little starting pitching the Yankees can confidently pencil into future rotations, they must consider a potential extension with Paxton. Their current top trio of Cole/Severino/Paxton projects as excellent next year, and it could do so well into the next decade, given Paxton has hardly shown any sign of physical decline. With few better options at their disposal, the Yankees should give Boras another call.