Taillon traded to Yankees for four prospects

The Pirates’ offseason tear down of the Major League roster continued Sunday, trading Jameson Taillon to the Yankees for four prospects.

Coming in return from the Yankees are right-handed pitchers Miguel Yajure and Roansy Contreras, infielder Maikol Escotto and outfielder Canaan Smith.

Contreras and Yajure were both on the Yankees' 40-man roster, so the Pirates had to designate Troy Stokes Jr. for assignment to open up a spot on the roster.

Shortly after the trade was made, Taillon took to Twitter to say goodbye:

While the Pirates are excited about the prospect return they are getting back, it wasn't easy to pull the trigger on the deal. Like he did after the Josh Bell trade on Christmas Eve and the Joe Musgrove trade from Monday, Ben Cherington said this move was made to get better in the future.

"I've said before, we've got to be willing to make decisions like this to add that kind of talent we're going to need to get this thing where we want to get it," Cherington said during a Zoom call Sunday afternoon. "We're excited about the four players we've added today from the Yankees. It's a combination of different kinds of players."

While most prospect lists are outdated this time of year and will be updated in the coming weeks before the season starts, Baseball America's team top 10s are up to date, and they had Yajure ranked as the Yankees' 7th best prospect in their 2021 list. Contreras was not ranked this year, but was 8th in their 2020 midseason update. A source says Escotto is highly thought of, even if he is not high on Yankees' list right now, and FanGraphs' Eric Longenhagen wrote at this time last year (pre-pandemic, of course) that Escotto and Smith could potentially crack his top 100 prospects list in 2021.

Yajure, 22, made his Major League debut, appearing in relief three times, though he profiles as a starter. His fastball sits in the lower-90s, but he makes up for it with a high spin curveball and cutter. He also throws a slider and changeup. 

Contreras, 21, has not pitched above class A, but was added to the Yankees' 40-man this offseason to protect him from the Rule 5 draft. He has a fastball-slider-changeup repertoire, all of which are graded as MLB average with some room for growth. He was ranked by Baseball America as the top Dominican pitching prospect for the 2016 international signing period.

Escotto, 18, signed for $350,000 out of the Dominican Republic in July of 2018. He hit eight home runs and stole 13 bases in 45 games for the Yankees' Dominican team in 2019. There are concerns of if he will be able to handle shortstop long-term, but FanGraphs praised him for having some of the best raw power in the Yankees' system.

Smith, 21, also has drawn praise for his power, homering 11 times with 32 doubles and three triples for the Yankees Class A team in 2019. His .871 OPS that year was the fourth best out of all qualified class A hitters. He hasn't gotten high marks with his glove and will probably profiles best as a left fielder, but he carries a real potential for pop.

In return, the Yankees get exactly what they were looking for: A high upside pitcher they could add without going over the luxury tax.

Taillon has not pitched in a game since May 1, 2019. He hit the injured list shortly after that start, and after several months of unsuccessful rehab and rest, he eventually needed Tommy John surgery, the second of his career. Few pitchers are able to come back from a second Tommy John, and virtually none return as starters, but Taillon is in position to do so after excelling in his rehab and overhauling his throwing mechanics, shortening his delivery.

Even with the very positive signs with his rehab and new mechanics, there is obviously a lot of risk in acquiring a pitcher coming back from a second Tommy John. The Pirates were open to listening to offers from him, but needed a large return in order to move him now rather than have him pitch for half a season to try to regain some trade value before the deadline.

Needless to say, the Yankees met their asking price after months of talk between the two clubs.

"In anticipation of that possibility [of trading Taillon], we spent a lot of time just looking at, where are we right now as a team," Cherington said. "Where’s Jamo? What can we reasonably project for him and the team over the next two years? Given that and give some reasonable projection of what he might do, what we might do over the next year or so, what would it have to take for us to do something now, this offseason, before we got a chance to see what it might look like with him coming back. We just tried to factor all of that in to the best we possibly could, comparing what was on the table now to what we felt like could be down the road, given a sort of reasonable expectation of a return and performance. We just felt like this made sense for us right now.”

Though the club has not formally announced a start date to spring training, pitchers and catchers will report to Bradenton, Fla. in three weeks, meaning there is not much time to make moves before the regular season starts. Cherington said he will "definitely keep the phone on" if teams want to inquire on players, and while there has been interest in some, there has been no traction to this point. He also said that he anticipates the front office will "likely shift our energy back toward adding to the team."

They are prioritizing starting pitching, because while the Pirates have acquired two rookie pitchers who could help out in the rotation immediately, they also did just trade their top two projected starters.

"There's a consideration to add back some major league starting pitching experience — somebody or multiples who have figured out how to do that at the major league level and can be a source of stability," Cherington said. "We’ll see where that leads us."