[3] He attended Brookline High School and was a classmate of Theo Epstein, later an executive with the Boston Red Sox and Chicago Cubs.

[4] He then attended Trinity College in Hartford, Connecticut, where he played baseball [5] and earned a bachelor's degree in 1995.

After an internship with the New York Yankees in 1995,[1] and a period in advertising sales with two major New York City radio stations, WABC and WFAN, Kennedy returned to baseball in 1996 with the San Diego Padres, where he worked under Larry Lucchino and was reunited with Epstein.

Kennedy began his San Diego career as an account executive, and had risen to executive director/corporate accounts and broadcasting when (along with Lucchino and, eventually, Epstein) he joined the Red Sox front office during the 2001–02 offseason upon the team's purchase by Fenway Sports Group (FSG).

[6] Lucchino's CEO post was initially left vacant, and on August 18, 2015, the Red Sox also named veteran MLB executive Dave Dombrowski to the new position of president, baseball operations.