[7] 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.
He documented that The New York Times (parent company of The Boston Globe) owned a 17 percent ownership stake in the Red Sox and that local sports talk radio leader WEEI was currently in negotiations for Red Sox broadcast rights and paid Lucchino for a weekly radio appearance.
[11] The timing of the column was notable as it came four days after Globe ombudsman Richard Chacón published an article in which he criticized Times management for accepting World Series rings from the Red Sox,[12] and three days prior to a Dan Shaughnessy column in which he revealed information detailing the nuances of the relationship between Epstein and Lucchino, to the favor of Lucchino.
[13] The information in the column was widely thought to have originated from Lucchino and may have contributed to Epstein breaking off negotiations and resigning his position as General Manager.
[14][15] In August 2006, Massarotti received some criticism for publishing a column detailing rumors that Red Sox pitcher Jon Lester was being tested for cancer.