With Jameson Taillon, the Yankees Add Upside and Risk

Pittsburgh’s sell-off continued over the weekend, with the Pirates sending starting pitcher Jameson Taillon to the New York Yankees in return for four prospects. The 29-year-old didn’t pitch in 2020, his season lost due to rehabilitation from Tommy John surgery in late 2019, the second such surgery of his career. Taillon, a former 2010 first-round pick, has suffered more than his share of setbacks, missing three years of his career and most of a fourth due to his elbow injuries and a sports hernia; he also missed time in 2017 due to testicular cancer. He heads to a Yankees rotation with a lot of interesting upside talent and a surplus of question marks.

Taillon’s departure to join former teammate Gerrit Cole in the Bronx represents the end of an era in Pittsburgh. Taken in consecutive drafts in 2010 and ’11, Taillon and Cole were frequently imagined together as the two aces at the top of a future Pirates rotation. For a team that had had recent first-round busts in the quickly injured Brad Lincoln and the bafflingly selected Daniel Moskos, this pair was the cornerstone of the rebuilding efforts of the then-new Frank Coonelly/Neal Huntington regime. Both pitchers were consensus elite choices in the draft and were selected without any of the team’s trademark cynical calculations about whether a player would sign on the cheap.

Taillon and Cole met their lofty expectations as they quickly worked their way through the minors. Cole, a college draftee, made his 2011 major league debut just two years after draft day, and if not for injury, Taillon would have likely followed him early in 2014. Missing two years is an enormous setback for any prospect, but the Pirates averaged 93 wins per season over 2013-15 and could afford to be patient. As the holes the team had to fill in order to continue winning increased, ownership’s commitment to investing in the roster did not, and the Pirates needed Taillon in 2016 more than they did in ’14 or ’15. And he succeeded, requiring only a 10-game tuneup at Triple-A before debuting in the majors and pitching well enough where he would have gotten some Rookie of the Year votes if he had been up for the entire year.

In 75 starts from 2016-18, Taillon put up 8.8 WAR thanks to a 3.63 ERA and a 3.53 FIP. Things were going so well that even the bout of testicular cancer that cost him six weeks in 2017 barely thwarted his success. Taillon was a big reason the Pirates briefly peaked above .500 at the end of the 2018 season, a year during which he didn’t just stay healthy but threw a professional-best 191 innings and tied for the National League in complete games with two (hey, it was 2018, not 1968). The ZiPS projections for Taillon were those of a pitcher who had made it:

Apparently healthy, Taillon unveiled a slider in 2018 and instantly became more of a swing-and-miss pitcher than ever before. The changes wrought by his new weapon were nearly instantaneous.

But instead of getting the opportunity to pitch a full season with his new repertoire in 2019, Taillon suffered forearm pain and was shut down in early May. After two months of rest and rehab, renewed elbow pain led to the second Tommy John surgery of his career. Taillon was well enough to pitch to live batters in late 2020, but the Pirates were adamant from the time of the operation that Taillon would not return to the mound until 2021.

Last August, the Pirates announced that Taillon wouldn’t return to a Major League mound until 2021 after undergoing his second Tommy John surgery. But if Taillon’s rehab continues to progress as well as it has so far, and if the season is delayed long enough, is it possible he’ll pitch this year after all?

In a word: No.

“I’d be lying if I said I hadn’t thought about it,” Taillon said, “but they’ve shut me down pretty quickly.”

The Pirates’ ship was dead in the water last season, so there was little practical reason to change the plan. And those calm ocean currents look even deader in 2021 thanks to the recent trades of Joe Musgrove and Josh Bell, no doubt smoothing the way for this deal.

I was initially underwhelmed at the Pirates’ return for a pitcher of Taillon’s talent level. But as disappointing as it feels to reunite Cole and Taillon for a playoff run in the wrong city, it’s undeniable that the Yankees are getting a pitcher who could throw 350 innings in 2021 and 2022, not one who will. As my colleague Eric Longenhagen discussed his piece on the prospects headed to Pittsburgh — go read it now if you haven’t already, then report back here — the Pirates acquired real prospects in return for Taillon. This team was not going to win in 2021 even if the trade hadn’t been made; even in baseball’s most dismal division, ZiPS was projecting the Bucs as a 50-to-1 shot to make the postseason. If the Pirates are really in the same category as the Rays where ownership simply will not aggressively invest in the team, they have to pull off moves like this to become relevant again at some point. This is the challenge that new general manager Ben Cherington was brought in to conquer.

For New York, the lure of this move is obvious. The team’s farm system has generally been very productive, but with the starting pitchers of nearly half of the team’s 2020 games (24 of 60) no longer employed by the Yankees, they needed to add another arm to the rotation. Taillon is a free agent after 2022, not 2021, and if he’s just healthy enough in one of these two seasons to bring 150 quality innings, the Yankees won’t blink at the loss of prospects who are generally years away.

That assessment might seem unduly negative for a team projected to have the third-best rotation in baseball prior to the trade, but this was a group that had some serious downside. Corey Kluber, Jordan Montgomery, and Luis Severino have all had very significant injury issues in their recent history, and it wouldn’t have shocked if two, or even all three, of this trio spent time on the injured list. This can’t be dismissed as simply a rerun of The James Paxton Experience, which the Yankees weathered well, because Masahiro Tanaka and J.A. Happ are no longer around as the dependable workhorses. The Yankees of old may have gone out and blown Trevor Bauer away with an ultra-lucrative offer, but this vintage of the organization has a desire to start the 2021 season under the soft-salary-cap-but-lets-play-imaginationland-and-call-it-a-luxury-tax threshold of $210 million.

In a perfect world (at least from the perspective of a Yankees fan), the Yankees would also bring in a veteran to throw 180 middling innings as a sort of firewall. But in this imperfect one, the team still has an excellent shot to end up with a top-five rotation in a league. ZiPS projected the Yankees as the best American League team prior to the trade, but only gave them a 58% chance to take the AL East thanks to the still-dangerous Rays and the newly aggressive Blue Jays. Adding another arm, even a risky one, gets the Yankees back over the 60-percent line, pushing them to 62% with a 90% chance of making the playoffs.

This trade is a win for the Yankees and, I’d argue, a win for the Pirates, though an obviously bittersweet one. Even if these prospects eventually lead the Pirates to NL Central supremacy, the idea of seeing Cole-Taillon reach the promised land together for another team come October isn’t a happy one for Pirates fans.