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Former Red Sox general manager Ben Cherington appears ready to take on a new challenge.

According to multiple reports, Cherington has been hired to head the baseball operations department of the Pittsburgh Pirates, replacing Neal Huntington — who played a role in helping Cherington land his first job in the Cleveland front office two decades ago.

Cherington served as Red Sox GM from October 2011 through August 2015, a volatile span in team history. He came aboard in the smoldering aftermath of the team’s chicken-and-beer collapse in 2011 and then lived through the insanity of the Bobby Valentine last-place finish in 2012.

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Yet in August of that year, Cherington helped orchestrat a franchise-altering trade to clear payroll by sending Adrian Gonzalez, Carl Crawford, and Josh Beckett to the Dodgers. He capitalized on his financial and roster freedom to execute a nearly a perfect offseason run of signings that set the stage for the championship season of 2013 while buying time for the team’s growing core of homegrown prospects to develop.

In 2014 and 2015, Cherington was at the helm for a rocky transition period of those young players to the big leagues, with the Sox suffering through back-to-back last-place finishes that ultimately resulted in Cherington being pushed aside so that the Red Sox could hire Dave Dombrowski in August 2015.

Yet Cherington’s patience with his prospects during those difficult years — including his refusal to trade players such as Mookie Betts, Xander Bogaerts, and Jackie Bradley Jr., his acquisition of Eduardo Rodriguez, the drafting of Andrew Benintendi, Michael Chavis, and Michael Kopech, and the signing of international amateurs Rafael Devers and Yoan Moncada — set the stage for the years of success that followed under Dombrowski.

After his separation from the Red Sox, Cherington took time outside the game to try to learn from his time in Boston. He taught a class at Columbia University before joining the Blue Jays as a vice president of baseball operations toward the end of the 2016 season.

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Though Toronto has endured three straight fourth-place finishes, its farm system — in which Cherington had a significant role — started to produce a talented young core in 2019 with the big league arrivals of Vlad Guerrero Jr., Cavan Biggio, and Bo Bichette.

Cherington declined at least one opportunity to interview for the Mets GM job in 2018 before emerging as the choice to lead the Pirates after Huntington’s dismissal following Pittsburgh’s last-place finish in the NL Central.

As was the case with his first GM job, one of Cherington’s first orders of business will be the selection of a new manager, as the Pirates elected to fire Clint Hurdle after the season.


Alex Speier can be reached at alex.speier@globe.com. Follow him on twitter at @alexspeier.