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.) https://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.

[Edit: Updated interview link and fixed spelling errors.]

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 (http://www.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.

In the last several weeks I’ve gone down a rabbit hole trying to figure out the meaning of ”My Old School.” Even though songwriters Donald Fagan and Walter Becker have never revealed much about their semi-autobiographical lyrics, many of the facts about the song have been nailed down. Still, some of the lyrics remain notoriously obscure, and we may never know their original intended meanings. I’ll try to lay out the known facts and offer my best theories about the parts that have remained unclear.

My comments are based on various Wikipedia articles, the Entertainment Weekly article mentioned in another post, contemporary newspaper accounts, and numerous other articles online. The EW article includes a particularly helpful interview with Fagan in which he talks about the events in the 1st verse of the song.

”My Old School” tells the story of Donald Fagen and his girlfriend getting into trouble with the law in 1969 when she visited him during his senior year at Bard College. At least that’s the main storyline. Fagen and Becker had met at Bard in 1967 when Fagen was a junior and Becker was a freshman. They quickly developed a close relationship and began collaborating musically. In a 1985 interview in The Bard Observer, Fagen was asked about ”My Old School.” He described the song as ”a personal story combining different experiences we both had at Bard. Also there were some fantasy sequences in there as well.” I believe this answer is the key to interpreting the lyrics.

Perhaps the biggest mystery about this song is why the lyrics alternate between addressing the girlfriend directly in the second person (”you/your”) and referring to her indirectly in the third person (”she/her/the girl”). Some have speculated that the third person references are about a female administrator at Bard or even about the college itself. But I couldn’t find any solid evidence for these interpretations...and they don’t actually fit the lyrics.

It’s a little complicated, but figuring out what’s going on with the pronouns is essential to understanding the lyrics. It turns out that the alternating pronouns divide the song into two distinct sections. All of the second person references (”you/your”) are in the 1st and 3rd verses, which I’ll call section A. And all but two of the third person references (”she/her/the girl”) are in the chorus and the 2nd verse, which I’ll call section B.

We know from interviews with Fagen and from newspaper accounts that the lyrics in section A are very likely about his long-term girlfriend, Dorothy White. So it would be reasonable to assume that section B is where the ”fantasy sequences” and Becker’s experiences are located. The lyrics in section B suggest that Becker had some kind of problem at Bard with a former girlfriend. The third person references in this section may have been a way to differentiate Becker’s angry feelings of betrayal from the romantic feelings Fagen expresses about his girlfriend in section A. But the bottom line is that, as Fagan implied in his interview, the song is probably a mashup of two separate storylines.

My line-by-line comments are in square brackets below. My personal theories are designated with ^.

SECTION A: VERSE 1
This verse is about a drug raid that happened when Fagan and Becker were students at Bard. Fagen is the narrator, and he directly addresses his girlfriend using ”you” or ”your.”

I remember the thirty-five sweet goodbyes [despite all the speculation about 35 being half of 69 if you round up, a simpler explanation is that ”goodbyes” refers to kisses^]
When you [Dorothy White, who was his girlfriend until at least 1975, six years after the events in the song and two years after the song was released; she painted the cover for the ”Countdown to Ecstasy” album and took the cover photograph for the ”Katy Lied” album] put me on the Wolverine [a passenger train that in the 1960s ran from New York City to Chicago via Detroit] up to Annandale [Annandale-on-the-Hudson, a hamlet in southeast New York state, where Bard College is located; one of the Wolverine stops was near Annandale]
It was still September
When your daddy was quite surprised
To find you with the working girls [prostitutes]
In the county jail [in May 1969 — here changed to September — Dorothy White visited Fagen at Bard a few weeks before his graduation; while she was there, she, Fagen, Walter Becker, and other students were arrested during a drug raid, according to local newspaper accounts; the raid was organized by the local district attorney’s office with the rumored cooperation of the college administration; Bard officials bailed out all of the 44 students who were arrested, including Fagan and Becker, but not White, who wasn’t a student; the charges against Fagen and Becker were eventually dropped]
I was smoking [pot] with the boys upstairs [around 4-5 AM in his off-campus residence]
When I heard about the whole affair [the drug raid; sheriff’s deputies had descended on the Bard dorms and off-campus student residences and were making arrests]
I said oh no
William and Mary won’t do [maybe he was worried he might get kicked out of Bard, but transferring to William and Mary in Virginia, wasn’t an option^; some have argued that Bard was known as ”the William and Mary of the north,” but I couldn’t find any solid evidence to support that idea; also consider that Bard is a small, private, liberal arts college in contrast to William and Mary, which is a public university and one of the eight public Ivy League schools]

SECTION B: CHORUS AND VERSE 2
Apart from the iconic refrain,”I’m never going back to my old school,” section B likely contains a mix of ”fantasy sequences” (fictional storylines) and Walter Becker’s account of his bad experiences with an old girlfriend.^ In this section the girlfriend is consistently referred to as ”she,” ”her,” or ”the girl.”

Well, I did not think the girl
Could be so cruel [it’s likely that this line is about one of Becker’s ex-girlfriends rather than Dorothy White — after all, songwriters typically don’t write revenge songs about their current girlfriends^; some have speculated that White cooperated with the police and gave them information about Fagen’s marijuana use, but available interviews and contemporary newspaper accounts don’t support this argument]
And I’m never going back 
To my old school [the narrator is so angry at Bard officials for their supposed complicity in the drug raid that after leaving Bard, he vows to never go back]

Oleanders growing outside her door [probably a metaphor for marijuana growing in Becker’s ex-girlfriend’s backyard^; songwriters in the 1970s had to make veiled references to marijuana; otherwise their songs wouldn’t have gotten much radio play; ”oleanders” might not be the perfect metaphor; but it does fit the rhythm and the melody; it’s also one of the most memorable and most singable words in the song, similar to ”I remember” and ”California”]
Soon they’re gonna be in bloom
Up in Annandale [he’s also growing marijuana at his off-campus residence^]
I can’t stand her [probably Becker’s ex-girlfriend^]
Doing what she did before
Living like a gypsy queen
In a fairy tale [this phrase paints a picture of someone living a nomadic, nonconformist, perhaps reckless lifestyle^]
Well, I hear the [Wolverine train^] whistle but I can’t go
I’m gonna take her down to Mexico
She said oh no
Guadalajara won’t do [this may be a ”fantasy sequence”^; the narrator had initially hoped to take his girlfriend by train to Mexico, possibly to avoid prosecution, but she refused to go with him^]

SECTION A: VERSE 3
This verse circles back to the drug raid from verse 1. We are back to Fagan as the narrator, and again he uses ”you” to refer to his girlfriend.

California tumbles into the sea
That’ll be the day I go
Back to Annandale [Fagen did eventually go back to Bard in 1985 to receive an honorary doctorate]
Tried to warn you
About Chino [this one is tough to pin down; ”Chino” is the Spanish-language term for people of Chinese ancestry, so this might have been a Chinese-American law enforcement officer with that nickname^; or it might have been a detective who liked to wear chinos slacks^] and Daddy Gee [before the drug raid Fagen had tried to warn Dorothy White about Chino and local assistant district attorney, G. Gordon Liddy, in his pre-Watergate days; Liddy had a reputation for being strict on drugs]
But I can’t seem to get to you
Through the U.S. Mail
Well I hear the whistle but I can’t go
I’m gonna take her down to Mexico
She said oh no
Guadalajara won’t do [these are the only occurrences of ”her” and ”she” in section A, which might seem odd at first; but Fagan and Becker are just repeating a refrain from section B]

^My theories

[Edit: Minor revisions]