In its March 24, 2006 edition, Entertainment Weekly details a return trip to Bard College in Annandale-on-Hudson, New York by Donald Fagen, in which he describes a raid by sheriff's deputies in May 1969. Fagen, his girlfriend Dorothy White, Steely Dan bandmate Walter Becker, and some 50 other students were arrested. Charges were dropped, but the harassment was the origin of the grudge alluded to in "My Old School". Fagen was reportedly so upset with the school being complicit with the arrests that he refused to attend graduation. The same article speculates that a Bard professor's wife, Rikki Ducornet, was the inspiration for "Rikki Don't Lose That Number".
Because of the reference to The College of William & Mary in the lyrics, "My Old School" has long been a favorite of W&M students and alumni, although the song is actually about Bard College.