My Old School

There was a long interview with Donald Fagen in Entertainment Weekly (EW) by Rob Brunner that I can no longer find on EW, but which is now posted on The Steely Dan Reader, which I've linked below. (You might want to skip to page 4.) steelydanreader.com/2006/03/17/back-annandale/

Here's a summary that I've put together from various sources including those here...

Fagen's high school girlfriend, Dorothy White, gives Fagen (ahem, half of "69") or "35 sweet goodbyes" before she sends him off on a train called the "Wolverine" to Annandale-on-the-Hudson, NY where Fagen would attend Bard College, sometimes referred to as "The William & Mary of the North". Bard's dean of students, (the girl who "could be so cruel") worked with the district attorney, G Gordon Liddy (Daddy G) and the local police to snitch and to drug-bust Fagen's dorm and arrest about 50 kids. The bust happens on a weekend that Dorothy is visiting and so Dorothy also gets arrested, as does Fagen who is "smoking with the boys upstairs" at 5AM.

Bard bails out the students, but not Dorothy since she's not a student, so her daddy has to bail her of jail (full of "working girls"). Fagen offers to take his increasingly bohemian girlfriend, Dorothy, to Guadalajara to avoid prosecution but she doesn't want to go.

Fagen was angry at Bard for its complicity in the bust and so he didn't attend graduation (when the whistle blows) and Fagen swears that he'd never going back to his old school. He also thinks that Bard doesn't deserve to be called "The William & Mary of the North". (So "William & Mary won't do".) Oleanders can't grow in New York's climate and apparently refer to cannabis (perhaps growing under UV lights).

Fagen did go back to Bard 16 years later, in 1985, to accept an honorary doctorate.

I think Outlander has some of this right, but the key is to note that his girlfriend (Dorothy White) is referred to in the song in the SECOND PERSON (You). The reference in the THIRD PERSON (She, Her, the girl) refers to Bard College

So when he says "I did not think the girl could be so cruel", he is referring to Bard College, since they allowed the drug bust to take place on campus and although they posted bail for the Bard Students, they didn't post bail for Fagen's girlfriend, Dorothy White, who was visiting at the time and got caught up in the drug bust. That's why "your daddy was quite surprised to find you with the working girls in the county jail", since the college did not post bail for her.

In the line "Tried to warn you bout Chino and Daddy Gee", I don't know who Chino is, but Daddy Gee is likely G. Gordon Liddy, who was the assistant DA at the time of the drug bust.

The line "I hear the whistle but I can't go" I believe refers to college graduation. Fagen boycotted his graduation because of the school's complicity in the drug bust.

Oh and the Wolverine was a train that used to go very near Annandale-on-Hudson, now it is just a Chicago-Detroit train.

The bottom line is this song is a kiss off to Bard College, NOT to the girlfriend. When you recognize that it is written TO the girlfriend and talking ABOUT Bard College, it makes more sense. Fagen feels bad about what happened to his girlfriend and blames the college for it.

By the way, according to a 2006 interview with Rollingstone Magazine (rollingstone.com/news/qa/story/9519861/donald_fagen_gets_inspired), Dorothy White was still Fagen's girlfriend as late as the designing of the album cover for Countdown to Ecstacy, which is the album this song was on.

Folks, song has nothing to do with Annandale Prison, Annandale, NJ, or Annandale, MD! Bard is in Annandale-on-Hudson, NY!

Oleanders are flowers that grow at Bard - it's not a reference to pot.

Bard '82

from wiki....

In its March 24, 2006 edition, Entertainment Weekly details a return trip to Bard College by Donald Fagen, in which he describes a raid by sheriff's deputies.[1] Fagen, his girlfriend, 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, although the song is about Bard College, "My Old School" has long been a favorite of W&M students and alumni.

To settle the Wolverine train debate....

The Wolverine was a train that ran from NYC through Rhinecliff, NC (whose main town there is Rhinebeck, NY). Rhinebeck and the Rhinecliff station is one of the nearest towns to Bard which is in the obscure hamlet of Annandale-On-Hudson. I remember that station well in the 70's - without fail I'd be waiting for a train to take me to NYC's Grand Central surrounded by harmless but interesting hare krishna's and a few 'moonines/ (The Rev Sun Myung Moon's 'college' campus/compound was right next to Bard in the 70's and accused of abducting/brainwashing some Bard students in the 70's)

By the way, other nearest town to Bard is Red Hook which is a rather backwards town with an aging population from another era just so you can appreciate the kind of politic there especially in the 60's and even later). I am not at all surprised this is the place from where G. Gordon Liddy hails - it figures (trust me, I know, I was a student at Bard back in the 70's and my first wife was from Red Hook). If they were tossed into the County jail then I suspect they were probably transported to Poughkeepsie where the county jail is located (Red Hook probably only had hold cells - so one has to wonder were were they actually held - in a holding cell in Red Hook or in Poughkeepise?)

Back to the train, the Wolverine was a train that ran from NYC to Detroit via Buffalo. it was actually the No. 17 which stopped at Rhinecliff station in the 60's. I believe the route was called the Empire State Express before 1976, was a daily passenger train operated by Amtrak between New York and Detroit via Buffalo and the Canadian province of Ontario. Prior to the formation of Amtrak in 1971 the Penn Central's Wolverine and Motor City Special had served the route, but Amtrak had truncated the Wolverine to Detroit and discontinued the Motor City Special.

I actually think the intended focal point is Fagen and Becker's drug bust. Good analysis, though.

Agreeing with MickeyPhilly, he was busted. Fagin was kicked out of prep school because he was caught "smoking with the boys upstairs" This is basically his story and reaction to that

This song isn't referring at all to the venerable College of William and Mary in Virginia.

Bard College, located in Annandale-on-Hudson, NY, is sometimes nicknamed "the William and Mary of the north". The Wolverine is a passenger train that once ran from Boston-New York-Detroit-Chicago and stopped close to Bard College.

The song's about a marijuana drug bust. The drug references are subtle: "smoking with the boys" and oleander (a plant that doesn't grow in New York's climate unless under an ultraviolet growth light).

The bitter narrator had an equally culpable female accomplice who turned state's witness in return for leniency.

OldJim is right. The original lyric was 34.5 but they didn't feel that it flowed well so they just rounded up.

There's probably a lot of inside jokes, but this is mostly about a girl who Becker or Fagin left behind when they went to college in Annandale, NY. She was very sweet when she took him to the train station to go to school, but before he'd been there a month, she was in trouble and wouldn't be able to go to college at William and Mary. She also dumped him. Spring comes and he still has hopes for the relationship, but she wouldn't go on a trip to Mexico they had planned. She's still acting like a wild woman instead of the sweet girl who saw him off on the train to college.

Ultimately he looks at it from some time later, living in California and thinking he's never going back to New York or that girl.