Pirates trade Jameson Taillon for prospects, reuniting him with Gerrit Cole on Yankees

Jameson Taillon and Gerrit Cole were No. 1 draft picks in back-to-back years for the Pittsburgh Pirates a decade ago, expected to serve as power pitchers who were the anchors of their starting rotation.

On Sunday, Taillon and Cole toasted to their reunion and a new future together with the New York Yankees with an Instagram caption that signaled the end of one era and the beginning of a familiar tune:

“Start spreading the news!!!”

Taillon is the final major piece of a total teardown by the Pirates, who traded their oft-injured ace to the Yankees for four prospects. In return, the Pirates acquired right-handed starting pitchers Miguel Yajure and Roansy Contreras, outfielder Canaan Smith and 18-year-old infielder Maikol Escotto from the Yankees.

With Yajure and Contreras added to their 40-man roster, the Pirates designated outfielder Troy Stokes Jr. for assignment, just 12 days after they claimed him off waivers from Detroit.

It was the third trade since Christmas Eve for Pirates general manager Ben Cherington, who sent All-Star first baseman Josh Bell to the Washington Nationals and 2019 Opening Day starter Joe Musgrove to the San Diego Padres in a three-team deal for a haul of 11 prospects.

“I would really just say a lot of the same things I said about Josh and Joe,” Cherington said. “Thinking about trading a guy like that, that’s always harder than thinking about the guys you’re getting back.”

The teardown started with Cole, who was traded to the Houston Astros for four players in January 2018. He signed a record nine-year, $324 million free-agent contract with the Yankees last year and recommended they pursue Taillon.

By trading Taillon, Cherington bid farewell to one of the team’s most popular players but one whose promising career was sidetracked by two Tommy John surgeries and testicular cancer. Taillon, 29, hasn’t pitched in a game since underoing the second UCL surgery in August 2019.

“Checks a lot of boxes as a teammate and as a pitcher, and we’ll wish him well and be rooting for him,” Cherington said. “That said, as 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.”

Baseball America ranked the 22-year-old Yajure (pronounced Yah-hoo-ray) the Yankees’ No. 7 prospect. MLB Pipeline ranks Yajure No. 15, Contreras No. 19 and Smith No. 21 in the Yankees’ system.

Taillon was the No. 2 overall pick in the 2010 MLB Draft — sandwiched between superstars Bryce Harper and Manny Machado — out of The Woodlands High School in Texas and signed for $6.5 million, the second-highest bonus ever at the time.

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Ten big-name Pittsburgh Pirates players have been traded by the team since Aug. 1, 2016.

Taillon’s path to the majors was marred by injuries, as Taillon had Tommy John surgery in April 2014, hernia surgery in July 2015 and also was hit in the back of the head by a comeback hit.

Taillon also had surgery for testicular cancer in May 2017, then returned to start five weeks later on his way to an 8-7 record with a 4.44 ERA

Taillon started 82 games over four seasons with the Pirates, going 29-24 with a 3.67 ERA. His best season was in 2018, when he went 14-10 with a 3.20 ERA, led the team with in starts (32), innings (191) and strikeouts (179) and threw two complete games, including a shutout.

Taillon followed by making his first Opening Day start and going 2-3 with a 4.10 ERA in seven starts in 2019 before being sidelined by elbow soreness. He required a second Tommy John surgery that August, and missed last season while rehabilitating at PNC Park all summer.

Even so, teams expressed interest in Taillon, who avoided arbitration by agreeing to a $2.25 million salary for 2021. He has one year of arbitration eligibility remaining. Cherington said the Pirates factored in how competitive they would be over the next two seasons, before Taillon becomes a free agent in 2023. They had the worst record in baseball last season (19-41).

“What can we reasonably project for him and the team over the next two years?” Cherington said. “Given that and given 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.”