Cherington had served as the Toronto Blue Jays' vice president of baseball operations since September 2016.
However, Cherington emerged as the Pirates' top target on Thursday, per Mackey. The 45-year-old executive was reportedly offered the job on Thursday, and after sleeping on it, he accepted it on Friday.
This marks just the latest stop in the big leagues for Cherington. He got his start as an advanced scout for the Cleveland Indians in 1998, and he joined the Boston Red Sox in 1999. He served as the team's director of international scouting and director of player development before being named the general manager in October 2011.
Cherington held the title of GM for three-plus seasons in Boston, helping the franchise win the World Series in 2013. He resigned late in the 2015 campaign after the club hired Dave Dombrowski as the president of baseball operations.
Toronto went 216-270 over the course of Cherington's three seasons at the helm, finishing in fourth place in the American League East each time. The Blue Jays' record has declined with each passing season since 2015, as their 67-95 mark in 2019 was their worst since 2004 (67-94).
In two of Cherington's three seasons on the job, Toronto's payroll ranked no lower than 11th in the majors, per Spotrac. Now, he faces the challenge of working with a limited budget.
Pittsburgh's $72.7 million payroll last season ranked 29th in the majors, with only the Tampa Bay Rays ($64.2 million) spending less. The Pirates have been in the bottom third in the league in payroll in every year since at least 2011.
Pittsburgh finished in last place in the National League Central in 2019 at 69-93, extending the team's postseason drought to four seasons.