Big Papi: My Story of Big Dreams and Big Hits, 2007, ISBN 0-312-36633-7, co-author David Ortiz, Professional Baseball Player for the Boston Red Sox
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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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In August 2006, Massarotti received some criticism for publishing a column detailing rumors that Red Sox pitcher Jon Lester was being tested for cancer.
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Knuckler: My Life with Baseball's Most Confounding Pitch, 2011, ISBN 978-0-547-51769-8, co-author Tim Wakefield, Professional Baseball Player for the Boston Red Sox
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