Lyric discussion by bilhuf 

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.

Entertainment Weekly:

ew.com/ew/article/0,,1174152,00.html

This link is very interesting. Could they be saying that the "35 sweet goodbyes" had to do with the 35 boys that got their heads shaved?

@bilhuf Love your analysis, but it's a little shaky around the first person/second person area. I still don't understand why there is a you and a she in there, but agree they're referring to different people. But the third person being Bard College falls apart with "Oleanders growing outside her door/Soon they're gonna be in bloom up in Annandale". The "her" can't refer to Bard College, because her door is obviously somewhere south of Annandale, the location of Bard. I don't have an alternate theory, but yours doesn't work.

@bilhuf Sorry, meant THIRD person/second. Another thing, he's "gonna take HER down to Mexico" and "SHE said 'Guadalahara won't do" (now) ... Anyway, I'm more confused than ever (now)

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