Regan was promoted to Director, Baseball Administration and Special Projects after serving as Assistant Director, Baseball Administration beginning November 2016. A native of West Roxbury, MA, Regan began his career with the Red Sox in 2010 as an intern in the Baseball Operations department. He has also served as Coordinator, Baseball Operations from 2014-16 and Assistant, Baseball Operations from 2012-13. A graduate of Trinity College, Regan was the captain of the school's Division III National Championship baseball team in 2008.