"My Old School" as written by Walter Carl Becker and Donald Jay Fagen....
I remember the thirty-five sweet goodbyes
When you put me on the Wolverine
Up to Annandale
It was still September
When your daddy was quite surprised
To find you with the working girls
In the county jail
I was smoking with the boys upstairs
When I heard about the whole affair
I said oh no
William and Mary won't do

Well I did not think the girl
Could be so cruel
And I'm never going back
To my old school

Oleanders growing outside her door
Soon they're gonna be in bloom
Up in Annandale
I can't stand her
Doing what she did before
Living like a gypsy queen
In a fairy tale
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


California tumbles into the sea
That'll be the day I go
Back to Annandale
Tried to warn you
About Chino and Daddy Gee
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


Lyrics submitted by AbFab

"My Old School" as written by Walter Carl Becker, Donald Jay Fagen

Lyrics © Universal Music Publishing Group

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My Old School song meanings
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  • +2
    General CommentI 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/…), 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.
    bilhufon June 14, 2008   Link
  • +2
    General CommentThere's an interview with Donald Fagan in Entertainment Weekly here. (You might want to skip to page 4.)

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

    Fagan's high school girlfriend, Dorothy White, gives Fagan (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 Fagan 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 Fagan'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 Fagan 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"). Fagan offers to take his increasingly bohemian girlfriend, Dorothy, to Guadalajara to avoid prosecution but she doesn't want to go.

    Fagan was angry at Bard for its complicity in the bust and so he didn't attend graduation (when the whistle blows) and Fagan swears that he'd never going back to his old schoool. 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).

    Fagan did go back to Bard 16 years later, in 1985, to accept an honory doctorate.
    RazzMcTazzon December 05, 2010   Link
  • 0
    General CommentThere'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.
    hayes6on December 10, 2004   Link
  • 0
    General CommentI actually think the intended focal point is Fagen and Becker's drug bust. Good analysis, though.
    MickeyPhillyon April 15, 2006   Link
  • 0
    General CommentAgreeing 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
    dueydrummer87on December 09, 2006   Link
  • 0
    General CommentThis 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.
    PrimoBabeon January 29, 2007   Link
  • 0
    General Commentfrom 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.
    mandalexon May 12, 2007   Link
  • 0
    General Comment35 sweet good byes - 35 is about "half of a 69" He got a good bye BJ.
    OldJimon August 18, 2007   Link
  • 0
    General CommentOldJim is right. The original lyric was 34.5 but they didn't feel that it flowed well so they just rounded up.
    tigerarmykevinon November 02, 2007   Link
  • 0
    General Comment1) Donald Fagen's girlfriend, Dorothy White, sends him off to school at Bard College in Annandale, NY on a commuter train called "The Wolverine" in the song. This probably was not the actual name of the train. He receives oral sex (35 sweet goodbyes)

    2) Dorothy White is arrested for drug posession, set up by dealers "Chino and Daddy Gee". Her father has to bail her out from the county jail, a place mostly populated by hookers (working girls)

    3) Dorothy sells out the drug users at Bard College, including Fagen, in exchange for a more lenient sentence. Fagen is arrested in a restroom smoking dope in May 1969 at 5am. The college cooperates with sherrif's deputies. Dorothy is on campus and is arrested in the sweep. Donald can't believe the "girl could be so cruel" as to sell him, Becker and their friends out.

    4) Fagen denounces the school - "William and Mary won't do" - a reference to Bard as "the William and Mary of the north" for its cooperation with authorities.

    5)Fagen is frustrated with his girlfriend's freewheeling lifestyle, but still loves her and offers to move with her to Mexico to avoid the drug charges. She refuses. He "hears the whistle" of court and possible jail time.

    6) Fagen again denounces Bard, saying that California will fall into the sea before he returns there and does not attend his graduation.

    7) Fagen says that he knew all along the dealers were no good, but Dorothy does not respond to his messages.

    *The drug charges are dropped due to bad evidence, but Fagen does not return to Bard until 16 years later, to accept an honorary doctorate after apologies. He does not hear from White again, and eventually marries Bard alumnus Libby Titus.

    Outlanderon December 21, 2007   Link

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