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He is a contributor to ESPN The Magazine, and a regular guest on a Sunday night sports show, Sports Xtra. Shaughnessy discusses sports and current events on radio shows airing on WTKK; on ESPN's Rome Is Burning; and on NESN's SportsPlus and Globe 10.0. On July 9, 2008, he made his debut as a guest host on the ESPN show Pardon the Interruption. He has a weekend radio show on WBZ-FM alongside Adam Jones.
Considered by some Red Sox fans (and some players) as being overly negative and critical, he earned the pejorative nickname "Curly-Haired Boyfriend" from former Red Sox player Carl Everett.
In an October 2005 column Shaugnnessy revealed information detailing negotiations between then-Red Sox general managerTheo Epstein and Red Sox CEO Larry Lucchino. Shaughnessy and other Globe writers were accused by writers at the Boston Herald of routinely reporting information leaked from the Red Sox front office (the Red Sox were 17.75 percent owned by The New York Times Company, the Globe's parent company). Then-Boston Herald columnist Tony Massarotti accused Red Sox management of smearing Epstein and suggested the Globe's coverage of the negotiations may be conflicted because of the Times ownership in the team. In the weeks leading up to Epstein's decision, Red Sox owner John Henry said the leaks "had to stop".
In 2013, Shaughnessy and Cleveland Indians manager Terry Francona released Francona, a biography focusing on Francona's years as manager of the Red Sox. The book immediately became a best-seller.