Simmons has, at times, had a tense and public battle with ESPN about creative freedom and censorship. In May 2008, Simmons was embroiled in a dispute with management at ESPN.com. When asked by the editors of Deadspin why he had not written a new column in over two weeks, he said that he was writing less because he loved writing his column and believed that he and ESPN had come to an agreement "on creative lines, media criticism rules, the promotion of the column and everything else on ESPN.com" but within a few months all of those things changed.