Shaughnessy worked part time for The Boston Globe from 1973 to 1977.[4] He has noted that his first byline with the Globe was on October 4, 1973, when he was a 20-year-old college junior.[5] Articles by Shaughnessy about the Boston Neighborhood Basketball League appeared in the Globe during the summer of 1974.[6]
Shaughnessy has authored or contributed to more than a dozen sports-related books, on topics including the fierce Yankees–Red Sox rivalry. His book The Curse of the Bambino details the travails of the Red Sox and their search for a World Series championship after selling Babe Ruth to the New York Yankees. He subsequently wrote Reversing the Curse after the Red Sox won the 2004 World Series.
Shaughnessy has been a contributor to ESPN The Magazine, and a regular guest on a Sunday night sports show, Sports Xtra.[9] He has also discussed 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.[10] On July 9, 2008, he made his debut as a guest host on the ESPN show Pardon the Interruption. He also had a weekend radio show on WBZ-FM alongside Adam Jones.
The 1980s Boston Celtics team furnished Shaughnessy with the sobriquet "Shank" for the often unflattering and critical nature of his articles.[11][12][13] Red Sox player Carl Everett, during a heated discussion with sportswriter Gordon Edes in September 2000, referred to Shaughnessy as the "curly-haired boyfriend",[14] a nickname sometimes referenced by Red Sox fans.[15][16]
In an October 2005 column, Shaughnessy revealed information detailing negotiations between then-Red Sox general managerTheo Epstein and Red Sox CEO Larry Lucchino.[17][18] 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).[19][20][21]Tony Massarotti, then a Boston Herald columnist, 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.[22] In the weeks leading up to Epstein's decision, Red Sox owner John Henry said the leaks "had to stop".
In 2013, Shaughnessy and Terry Francona released Francona, a biography focusing on Francona's years as manager of the Red Sox. The book immediately became a best-seller.[23]
Shaughnessy was named the 2026 recipient of the Red Smith Award, presented annually by the Associated Press Sports Editors (APSE) organization for outstanding contributions to sports journalism.[25]
