On June 10, 1997, in the 5th inning of a game against the Anaheim Angels, Howard hit a long fly ball over the head of Jim Edmonds.

Edmonds would make a spectacular over-the-shoulder diving catch to rob Howard of extra bases.

He moved into their front office at the close of the 2007 season, spending 2008–09 as special assistant to Boston general manager Theo Epstein.

In 2010, he succeeded Rob Leary as the Red Sox' field coordinator of minor league instruction and served in that role through 2018.

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