The 1980s Boston Celtics team furnished Shaughnessy with his now-famous sobriquet, "Shank," for the often unflattering and critical nature of his articles.

His book, The Curse of the Bambino, details the travails of the Boston Red Sox and their search for a World Series championship after selling Babe Ruth to the New York Yankees.

[7] 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.

[12][13][14] 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.

[15] In the weeks leading up to Epstein's decision, Red Sox owner John Henry said the leaks "had to stop".