Cherington was known for his emphasis on building a strong farm system and developing young talent. He oversaw the drafting and development of several key players who played a role in the Red Sox's championship run, including Mookie Betts, Xander Bogaerts, and Jackie Bradley Jr. He also made several key trades and free agent signings, including the acquisition of pitcher Jon Lester and the signing of outfielder Shane Victorino.
After leaving the Red Sox in 2015, Cherington took a year off from baseball before joining the Toronto Blue Jays as their vice president of baseball operations in 2016. He helped lead the team to back-to-back playoff appearances in 2016 and 2017. In 2019, Cherington was hired as the general manager of the Pittsburgh Pirates, where he oversaw a rebuilding effort focused on developing young talent and building a sustainable winning culture.
Cherington's tenure with the Pirates was cut short in November 2020 when he resigned from his position. He cited a desire to spend more time with his family and pursue other opportunities in baseball. Despite his relatively short time with the Pirates, Cherington was widely respected for his commitment to building a strong foundation for the team's future success.
Throughout his career, Cherington was known for his analytical approach to baseball and his ability to build strong relationships with players, coaches, and front office staff. He was widely regarded as one of the top executives in the game and was often sought after for his expertise and insight. While his time in baseball may have come to an end, Cherington's impact on the game will be felt for years to come.
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