Bennett didn’t commit gaffes so much as use his bully pulpit to lob rhetorical bombs into the education establishment. Among his most memorable was a 1987 statement about the Chicago public schools. "I’m not sure there’s a system as bad," Bennett said at a forum with reform-minded business leaders in the city. "If there’s one that’s worse, I don’t know where it is." The remark stung in Chicago and contributed to a wave of state-sponsored changes.

Paige was meeting privately with a group of governors at the White House in 2004 when he responded to a question by likening the National Education Association to a "terrorist organization" because of its efforts to resist key provisions in the federal No Child Left Behind Act. Paige responded to an uproar by apologizing, saying he was aiming criticism at leaders of the nation’s largest teachers’ union, not teachers themselves.

Duncan had two major gaffes during his seven-year tenure. In 2010, Duncan told a TV interviewer that "the best thing that happened to the education system in New Orleans was Hurricane Katrina." Duncan quickly apologized for his reference to the deadly 2005 hurricane.

In 2013, Duncan created a firestorm when he said some opposition to the Common Core State Standards was coming from "white, suburban moms" who discover that their children aren’t as "brilliant as they thought they were and their school isn’t quite as good as they thought they were." Duncan apologized for his "clumsy phrasing."