Massarotti joined the Boston Herald in 1989, and covered the Boston Red Sox for the paper from 1994 through 2008.
During his time with the Herald, Massarotti frequently covered the Red Sox for Fox Sports New England, and appeared occasionally as a guest on WHDH's Sports Xtra. He also appeared on Boston's WEEI sports talk radio program The Big Show. These appearances ended with his later leaving the Herald for the Globe due to a long standing ban on Globe staffers appearing on the station.
While with the Herald, Massarotti was known for his staunch support of former Red Sox managers Jimy Williams and Grady Little, despite Little's controversial decisions, during Game 7 of the 2003 American League Championship Series.
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