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Pirates pitcher Jameson Taillon works through drills on the mound during summer camp at PNC Park on Thursday, July 9, 2020, on the North Shore.
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Why the Pirates were comfortable trading Jameson Taillon now

Matt Freed / Post-Gazette

Why the Pirates were comfortable trading Jameson Taillon now

Jameson Taillon was supposed to take the ball in Chicago or Pittsburgh at the beginning of April, a symbolic start synopsizing his long, arduous journey back from a second Tommy John surgery.

Although Taillon had battled injuries throughout his Pirates career, not to mention surgery for testicular cancer in May 2017, the right-hander figured there would be some extra oomph behind this one, with Taillon wanting to show the baseball world that he’s hardly finished.

Now, that emotional performance will come in Yankees pinstripes after the Pirates traded Taillon to New York on Sunday for a package of four prospects, their third significant rebuilding move since Christmas Eve.

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"I know what kind of pitcher [Taillon] is," general manager Ben Cherington said on a Zoom call. "Checks a lot of boxes. We wish him well, and we'll be rooting for him. That said, we’ve got to be willing to make decisions like this to add the kind of talent we’re going to need to get this thing where we want to get it."

Injured starting pitchers Trevor Williams and Jameson Taillon walk to the dugout during batting practice Friday, May 31, 2019, at PNC Park. (Matt Freed/Post-Gazette)
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The players the Pirates are getting back include right-handed pitchers Miguel Yajure and Roansy Contreras, infielder Maikol Escotto and outfielder Canaan Smith. Yajure and Contreras will step into spots on the 40-man roster, which forced the Pirates to designate Troy Stokes Jr. — claimed off waivers from Detroit on Jan. 12 — for assignment.

Baseball America considers Yajure the eighth-best prospect in the Yankees organization, while Contreras is 11th, Smith 16th and Escotto 32nd.

Whether they should trade Taillon was a question that has swirled around the Pirates’ offseason to this point. Given his last in-game action came May 1, 2019, when the No. 2 overall pick in 2010 pitched well and won in Texas, it was tough to predict any possible return.

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Would teams hesitate to offer much because of Taillon’s injury history, which has limited him to just 466 innings since his MLB debut in 2016? Or would they buy low ($2.25 million salary in 2021) and hedge their bets that several recent mechanical changes will allow Taillon to reprove himself as a front-line starter?

Even Cherington said the Pirates didn't really know. It would ultimately come down to return, with those four players and the full-scale rebuild sending Taillon to the Big Apple.

"It's super, super bittersweet," Taillon told the Post-Gazette. "I was so comfortable with the organization that it was truly like a family to me. I knew everyone. I’ll definitely miss that side of it. But I totally understand [the trade], and I'm fired up to jump into such a legendary, winning organization."

The Yankees represent a fine fit, too. Taillon and ace Gerrit Cole were close in Pittsburgh and have remained in regular communication. When Cole thrust himself into a different stratosphere with the Astros, becoming arguably the best in the game, Taillon would routinely show up at Minute Maid Park to watch and cheer his friend.

Pirates team owner Bob Nutting talks with general manager Ben Cherington during spring training Monday, Feb. 17, 2020, at Pirate City in Bradenton, Fla.
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When the Pirates traveled to Houston in 2019, Cole and Taillon made plans to hang out and cook dinner. Now, it’ll be on Cole to show his rotation mate around the Big Apple.

Perhaps recognizing that the Pirates have shifted into fire-sale mode, opposing teams have been keeping tabs on Taillon this offseason, analyzing his previous work, talking to scouts and trying to project his performance. According to one source, the Pirates had offers from at least three clubs, with the Yankees emerging as the front-runner on Saturday.

The players the Pirates are getting back certainly fit what they’ve done this offseason by prioritizing youth and upside. That started, in earnest, with the Josh Bell trade netting right-hander Eddy Yean, who’s now ranked No. 8 on Pittsburgh’s prospect list by MLB Pipeline.

In the Joe Musgrove trade, the Pirates picked up 19-year-old outfielder Hudson Head from the Padres, who’s now No. 6. Other players picked up in those trades — left-hander Omar Cruz (No. 18), righty Wil Crowe (No. 19), catcher Endy Rodriguez (No. 20) and right-hander David Bednar (No. 30) dot their top 30.

Look at that entire list, and 14 of the players on it have been added since Cherington was hired. That also does not include Shalin Polanco, an outfielder the Pirates signed for $2.35 million on Jan. 15. No Pittsburgh position player has ever received more on the international market.

So when you look at the Taillon trade through that lens — the Pirates undergoing a full-scale rebuild — it makes all the sense in the world to act now and minimize any potential risk with Taillon.

"These things are hard," Cherington said. "They’re always going to be hard when it involves a player who is well-liked and who’s performed well at the major league level like Jameson has."

For now, though, it’ll be to miss Taillon, who won fans over with the way he carried himself and also tantalized with his talent, going 29-24 in 82 starts. He pitched to a 3.67 ERA with an average of 8.1 strikeouts per nine but also missed nearly half of the 150 starts he could've made in a Pirates uniform due to various injuries.

Given where they're at, however, it made more sense for the Pirates to take the sure thing rather than make an emotional decision like keeping Taillon around.

“I have a ton of respect for [Taillon]. He totally gets it,” Cherington said. “We would hope this one works out well for everyone — the Pirates, Yankees, Jamo and the players we’re getting back.”

Jason Mackey: jmackey@post-gazette.com and Twitter @JMackeyPG.

First Published: January 24, 2021, 5:31 p.m.

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