PITTSBURGH -- When the offseason began, Pirates general manager Ben Cherington knew there would be trade interest in some of the Pirates’ veteran players, but it was hard to say if -- or how quickly -- things would come together.

“We didn’t really know,” Cherington said. “We just wanted to be prepared to act if the opportunities came our way.”

Now, after acting on a trio of course-changing trades, the Pirates’ farm system has been revitalized. Their most recent move came Sunday, dealing Jameson Taillon to the Yankees for four prospects: right-hander Miguel Yajure, right-hander Roansy Contreras, outfielder Canaan Smith and shortstop Maikol Escotto.

The headliner of the package for the Pirates is Yajure, whom Cherington called the “most advanced” player of the group. Yajure, 22, made his MLB debut in 2020, retiring the side on six pitches in his first inning before going on to allow one run in seven innings with eight strikeouts.

Ranked as the Pirates’ No. 14 prospect by MLB Pipeline, Yajure led all Yankees prospects in 2019 with a 2.14 ERA, using a mix of a 92-95 mph fastball, a cutter, a curveball and a changeup. Cherington expects Yajure to be in Major League camp as a starter “with a chance to contribute in 2021, hopefully.”

Somewhat surprisingly, Cherington also believes that 21-year-old Contreras could pitch in Pittsburgh as a starter this year. The right-hander has not pitched above Class A, a level at which he posted a 3.33 ERA and a 1.07 WHIP in 24 starts with Charleston in 2019, but with the coronavirus pandemic having erased the '20 season, prospects have been making the jump from Class A to the Majors more often.

“I think given the performance there, given what he's done the last year to continue growth, he's on the roster now,” Cherington said. “Likely needs some more development time, but he's someone who we're really encouraged by. We think he has a chance to be a starting pitcher and be in that next wave of pitching depth.”

Contreras is considered by MLB Pipeline to be the Pirates' No. 19 prospect.

To make space for Yajure and Contreras on the 40-man roster, the Pirates designated for assignment Troy Stokes Jr. Stokes was claimed off waivers from the Tigers on Jan. 12.

Smith, 21, has built a reputation as a skilled player at getting on base, drawing a South Atlantic League-leading 74 walks in 124 games at Class A Charleston to help produce a .307/.405/.475 line. The left-handed hitter, who is now the Pirates’ No. 26 prospect, also showed strides with his swing that season, recording 32 doubles, three triples and 11 homers.

“He's been a really good performer [with] a combination of plate discipline and just really good quality contact,” Cherington said. “We really felt like he was one of the better hitters in the South Atlantic League a couple years ago, and again, [he’s] now had another year of physical growth.”

The most untested prospect of the group is Escotto, an 18-year-old shortstop who was signed out of the Dominican Republic in 2018. But his first taste of professional baseball was successful at the Rookie level, as he posted a .981 OPS in 45 games, and he’s someone who has been on the Pirates’ radar for a while.

“Some of our scouts liked him even back to when he was an amateur on the international market,” Cherington said.

The move on Sunday was one in a line of trades and transactions the Pirates have made to bolster their farm system since the 2020 season has ended. Gone are Pittsburgh mainstays including Josh Bell, Joe Musgrove and Taillon, and here for the future are 10 of the club’s Top 30 Prospects, among other depth pieces and lower-level talents.

• Bucs land 2 pitching prospects for Bell | Pirates get 5 prospects for Musgrove

By acquiring not only highly regarded prospects but also a deep base of young players, Cherington hopes the moves set up the Pirates’ renovated development arm for as much success as possible. He said he recognizes that not every player the club takes a chance on “is going to pan out,” but he hopes the synthesis of quantity and quality prospects will put the organization on good footing going forward.

“We just need lots of them and then we’ve got to really pore into development,” Cherington said. “Especially in deals like this, the acquisition is one half of it and the development is just as important. We’ve got to pour into that now.”