A 2006 Entertainment Weekly article, “Back to Annandale” explains the backstory of “My Old School.”

But just outside of Adolph’s, he sees it. The house. ‘'Right there is the house that I was busted in,’‘ [Donald Fagen] says, gesturing toward a two-story structure nearby. Here, finally, lies the story behind ’‘My Old School.’'

It was around 5 a.m., a Thursday in May 1969, when a swarm of sheriff’s deputies descended on Bard, sweeping through dorms and off-campus residences, including this small house, where Fagen lived with a roommate. ‘'They went up and down the halls, knocking on doors,’‘ says [friend] Terence Boylan, who was in his room at Ward Manor at the time. ’‘Toilets were flushing everywhere to get rid of any pot that you had. I threw mine out the window. All you had to do was say to the cop, 'What are you doing?’ They’d say, ‘That’s it, resisting arrest.’ Somebody would say, ‘What the hell is going on?’ ‘Oh, profanity! Arrest him.’‘’ Fagen, Becker, and Fagen’s girlfriend, Dorothy White, were all dragged off to jail.