The "Old School" referred to in this song is Bard College in Annendale, New York, where Donald Fagen and Walter Becker met. The song is at least partially inspired by an event that occurred at Bard, where both Becker and Fagen, along with their girlfriends, were arrested in a pot raid on a party that was orchestrated by an ambitious young District Attorney named G. Gordon Liddy (hence the line "Tried to warn ya about Geno and Daddy G"). Despite the fact that California has not (yet) tumbled into the sea, both Fagen and Becker have returned to Bard.
The "Wolverine" in the line "when you put me on the Wolverine up to Annandale" is the train that went to Annendale to take Fagen and Becker to Bard.
Following "Show Biz Kids," "My Old School" was the second single from Steely Dan's second album, Countdown To Ecstasy. It's one of the most horn-heavy Dan tracks, with four saxophones arranged by Jimmie Haskell. It also features guitar solos by Jeff "Skunk" Baxter and plenty of piano from Donald Fagen, who was also their full-time vocalist at this point. On their first album, Can't Buy A Thrill, David Palmer sang lead on some of the tracks, including "Dirty Work."
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