Hiaasen traces his strong sense of right and wrong back to the losses of the 1960s—the "complete end of innocence" caused by the Kennedy assassinations, two tragic events creating the historical circumstances that placed Richard Nixon in the White House, accelerated the war in Vietnam, and ultimately led to Watergate. "It was a poisonous time to be coming of age," Hiaasen says. "It seemed to me there was so much wrong in the world. I felt such outrage for so many years over those things happening that it wasn't a hard thing to carry into journalism."

When Hiaasen began his Miami Herald column in 1985, however, after having first been a general assignment reporter and then a member of the Herald's prize-winning investigation team, the newspaper hadn't yet established a tradition of commentary written with "ferocity and passion, mordant wit, and moral outrage," as Doug Clifton, former executive editor of the Miami Herald, describes Hiaasen's bi-weekly column. Miami was still a young city, Hiaasen explains, with no voice, even on the editorial page, that expressed strongly held opinions likely to inspire an equally strong response from readers. So when Hiaasen ridiculed the first Cuban American county manager, whose indictment for grand theft was dismissed because of a 1951 ruling on cattle rustling ("a standard of conduct against which all public officials should be tested," Hiaasen dryly observed), Herald editors initially cringed. Interestingly, however, the following year that same county manager forgot to disclose, as required by law, a large profit he made on a land deal, prompting Hiaasen to write that such memory lapses by someone controlling the county budget suggested the need for a brain scan in addition to a lawyer: "If I thought [he] deserved to be fired for lying to the IRS and buying stolen suits and lying about it, I would say that in the column. Gotta get rid of the guy. And it was unheard of at the time."