Chicago: City of a Thousand Faces

“Chicken in the car and the car can’t go, that’s how you spell Chicago.” I heard that jingle when I was a boy and have never forgotten it. I’m writing this on the cusp of the 2024 Democratic National Convention. By the time you read it the convention will probably be history. After all these years — more than 50 — I have never forgotten the brief time I worked in the Chicago office of Students for a Democratic Society (SDS) during the summer of 1969, soon after the conclusion of the Democratic National Convention and the riots in the streets. Chicago struck me as "cop city," more than New York where I had tangled with cops and was arrested and jailed. The Chicago cops looked meaner than New York cops.

I didn't want to tangle with them, nor did I want to tangle with the gang members who belonged to the Black P. Stone Nation who hung around the entrance to the SDS national office on West Madison Street, and taunted white guys like me. They called us names and referred to SDS as “Sdooey.” Or something like that. I’m unsure of the spelling or pronunciation.

I lived in a small apartment in a white working class neighborhood bulging with immigrants from Europe and their off-spring who didn’t forget they were Slavs and who felt uncomfortable around Black people. I shared the apartment with Kathy Boudin, daughter of famed lefty lawyer, Leonard, and her boyfriend, David, who was a master printer who ran off SDS leaflets and pamphlets but didn’t consider himself a radical. Politics just weren’t his thing. He was attached to Kathy and probably would have followed her to the proverbial ends of the earth.

He and I followed Kathy every morning to the SDS office, where I spent an inordinate amount of time writing and rewriting a propaganda piece that Terry Robbins, a hot shot organizer from Kent State, called “a shotgun.” Terry was obsessed about guns and bombs. In March 1970, he and two other SDS members, who had helped to create Weatherman, accidentally blew themselves up in an apartment building in Manhattan. But perhaps if you’re an amateur terrorist and you’re making a bomb there are no accidents.

The blast so thoroughly blew Terry into bits and pieces that it took much more time to identify his remains than it took to identify the bodies of Teddy Gold and Diana Oughton. The apartment building was destroyed.

For a few weeks, I slept in the same Chicago apartment with Kathy and her boyfriend David, but like them I spent 14 to 15 hours a day in the SDS office which came to feel like a bunker. We were isolated, and we were prisoners of a sort lodged in enemy territory. Perhaps that situation was emblematic of SDS, once a large, vibrant student anti-war organization that dissolved into a left-wing faction. A footnote to history.

I departed from Chicago after the start of the Chicago Conspiracy trial and after the Weathermen launched their Days of Rage, which Black Panther firebrand, Fred Hampton, called “Custeristic.”

He meant doomed. Hampton was dangerous, too dangerous for Chicago. Local, state and federal law enforcement agents banded together and assassinated him while he slept, along with Mark Clark and several other Panthers.

I was surprised but not shocked. I knew that Chicago cops, Illinois cops and FBI agents didn’t fool around in 1969, when it seemed, even to sane individuals, that the whole nation might explode and blood might run down every street in our apocalyptic nation.

I did return to Chicago in the fall that followed the summer I worked in the SDS office. I went to Chicago to find my wife who might or might not have been underground plotting some kind of conspiracy with fellow conspirators. I did find her with help from Bill Kunstler, the lead lawyer for the defendants in the Chicago Conspiracy Trial which was held in Judge Julius Hoffman federal courtroom. Kunstler always knew where and how to find everyone on the left.

I asked my wife to come back to New York, to our apartment and try to rebuild our marriage. She didn’t say she would. In fact, she called me a “sex addict,” whatever that meant. I certainly didn’t see myself that way. I think she just wanted to hurt me and push me away. I didn’t see her again until early 1970 when she was even deeper underground than she had been before.

I didn’t go back to Chicago until the late 1990s when I was researching my biography of Abbie Hoffman that would be published as For the Hell of It. I stayed with Bernardine Dohrn and Bill Ayers, their two sons and the son of Kathy Boudin and Dave Gilbert who were in prison after a botched robbery of a Brinks truck. Bill and Bernardine were living more or less quiet lives; they had each made their separate peace with law enforcement and never went to jail for anything they said or did when they were underground. “That’s America,” Bill quipped. I followed Bill around Chicago where he spoke to civic groups and defended everything the Weather Underground had done including the bombings which he felt forced the US to pull out of Vietnam.

Bernardine had a job in academia. She seemed like a model mother. When the boys wanted matzo ball soup she made it from scratch, and, when they played baseball she sat in the bleachers and cheered. I cheered with her.

Now, what I remember most about Chicago — aside from the cops and their fascistic uniforms, and my sad, sad meeting with my wife — what I remember most is Carl Sandburg’s working class poem, “Chicago” in which he calls the city “wicked,” “crooked,” “brutal,” “cunning,” and ends by describing it as “proud to be Hog Butcher, Tool Maker, Stacker of Wheat, Player with Railroads and Freight Handler to the Nation.”

Looking back, I'd say that Chicago is a mythic city with endless faces that keeps on reinventing itself. Maybe we'll rendezvous again.