The main riff comes from an unfinished jam the Providence band Subramayan recorded in 1997. I always wanted to turn it into a real song for Tristan Da Cunha and I eventually wrote some words and a melody. TdC actually did work on it at one practice in the summer of 2010. It was Steve Budney who suggested the off-kilter timing. However, we got busy finishing up other songs for the Compass album and a year later, the band was done.
As far as the chorus goes, I didn't actually have "the man" myself but I certainly could hear him screaming at his classes across the courtyard at Somerville High in the early 90's. And I definitely knew all the stories about him. The song is not really about him though. One of his catchphrases ended up as the title of the song.