Cherington led the Red Sox to a World Series win in 2013, but he left the team last season after Dave Dombrowski was hired as the president of baseball operations. Instead of returning to baseball right away, Cherington chose to teach a semester at Columbia University.

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The Blue Jays’ new front office addition has been credited with acquisitions of young stars such as of Mookie Betts, Xander Bogaerts, Jackie Bradley Jr. and Andrew Benintendi to the Red Sox organization. However, some high-priced additions — namely Pablo Sandoval — did not work out in his favor.

It was reported other teams were interested in Cherington, and that he skipped a meeting with the Minnesota Twins, according to Yahoo Sports. He instead decided to stay within the familiar AL East and try to help lead the Blue Jays to a World Series.