#369: The Dill Pickle Club, 2014

September 5th, 2014

There once was an orange door

Down an alley off the ritzy street.

Down the alley, on the right side, the backs of houses. Luxury houses. Fancy brownstones a couple million a pop in the Near North Side. People walk toy dogs here.

On that right side of the alley, a lanky man in a polo shirt and expensive haircut starts an electric barbecue grill in a fenced-in back staircase. “Honey,” he calls, turning his head toward an unseen woman inside.

On the left side of the alley, a three-level parking garage. The fronts of SUVs and crossovers peek through the chain link saving the parked cars from alley dwellers like me and whoever scribbled “Trust Only Vandals” on one of the Dumpsters.

There once was an orange door here.

There once was an orange door and a sign that said “Step High, Stoop Low, Leave Your Dignity Outside.”

This yuppie alley once housed the Dill Pickle Club, the center of bohemian counterculture in the 1920s.

Bohemian rhapsody

Picture Wicker Park in the 1990s, Old Town in the 1960s, Logan Square 10 years ago, any place that used to be cool, man, and you should have seen it then.

That’s what Tower Town was in the 1920s. The neighborhood around the Water Tower lured poets, artists, drunks, dope addicts, homosexuals, musicians, anarchists, socialists, painters and all manner of gadflies to what was then a slum.

They would watch the soapbox forum at nearby Bughouse Square, sit in on a “class” at the Hobo College and top it off with a visit to a tearoom like the Wind Blew Inn or the Dill Pickle Club.

“The street car conductor sits on a bench beside the college professor, the literary critic, the earnest young wife, who hungers for culture, and the hobo,” novelist Sherwood Anderson wrote of the Dill Pickle in 1919.

The Dill Pickle, sometimes Dil Pickle, had its origins in the early 1910s, when a labor organizer named Jack Jones started a weekly forum at the Radical Book Shop on Clark Street (that spot now a US Bank). They preached anarchy, sex and revolution in an era when straw boater hats were still used mostly for boating.

Soon it grew, soon they got a spot on Tooker Place, what’s now that little alley with the barbecuers and peeking crossovers.

A few strange debates

The Dill Pickle Club was known for its strange lectures and debates.

  • A lecture on the Theory of Relativity was billed as “Should the Brownian Movement Best Be Approached from the Rear?”
  • A 1931 lecture by a practicing German homosexual brought a record crowd of 300 people at a time when sodomy was a felony in every U.S. state.
  • Ben Hecht, who created the project this blog is based on, debated poet Max Bodenheim on the topic “Resolved: That People Who Attend Literary Debates Are Imbeciles.” Hecht walked up, gestured at the audience and said “The Affirmative rests.” Bodenheim, who would later be known as “The King of the Greenwich Village Bohemians,” got up and said “You win.”


“The Dill Pickle occupied a row of remodeled barns in Tooker Alley,” poet Kenneth Rexroth wrote in his autobiography. “Out the alley and around the corner was Bughouse Square, where every variety of radical sect, lunatic religion, and crackpot health panacea was preached from a row of soapboxes every night in the week when it wasn’t storming. The soapboxers, or at least the political radicals among them, hung out in the Dill Pickle and constituted the inner core of club membership. Then there was a group of girls who were almost all prostitutes who had drifted in off North Clark Street, lonely for coffee and company, as whores always are. In the course of time they became the mistresses of various newspapermen, IWW, Anarchist, and Socialist leaders who hung around the place.”

The place became a speakeasy in 1920, booze bringing a shining roughness to the crowd that coffee alone couldn’t manage.

Hecht would often be found there, scribbling his 1,001 stories at a table behind the bar.

The Pickle in the ’30s

A bohemian Daily News reporter named John Drury wrote this about the Pickle in a 1931 restaurant guide.

“Are there people living here who haven’t heard of the Dill Pickle Club? What Mecca is to a Mohammedan the Dill Pickle Club is to the bohemians of Chicago — and to those who merely come to see the bohemians. It is a center of night life activities in Tower Town and is the most often visited and most often denounced of near north side bohemian haunts. The walls are adorned with garish paintings, the dance room is dark and dusty and dimly-lit, the little theatre is awfully little, the garden is popular on summer nights, and the coffee shop serves coffee and a few light foods that are tolerable. Jack Jones, the bushy-haired, who founded the Dill Pickle, and his mild-mannered sister prepare goodly assortment of sandwiches for the Wednesday night literary crowd, the Saturday night dancing and drama crowd, and the Sunday night lecture crowd. Don’t miss the Dill Pickle. It is not a club but a free-for-all place.  Delaware 0669.”

Rexroth wasn’t as kind to the 1930s Pickle.

“As the years went on, Jack got old and pretty crazy, the Dill Pickle grew more and more vulgar, was finally taken over by the Organization and turned into a rough and fraudulent operation,” he wrote.

By the time it closed, Rexroth wrote, “The Pickle had long since become a dangerous tourist trap.”

A scandal in bohemia

The Pickle closed sometime between 1933 and 1935 – sources vary. Jones tried to restart it a few times, each meeting with failure. He found some work as a WPA painter, but died penniless of a heart attack in 1940.

Drury and his wife Marion Neville moved to Chesterton, Ind., in the 1940s as part of an “ex-urbanite” movement of artistic types trying to get back to the land. The pair were both freelance writers by then (Drury had left the Daily News in 1944 to host a soon-canceled radio show about fine dining), so leaving a city full of stories turned out to be a terrible idea.

They struggled with poverty and, in Drury’s case, alcoholism until Neville died of cancer in 1967. Drury died in 1972.

Rexroth would slip off to San Francisco and become one of the many godfathers of the Beats (he was “Reinhold Cacoethes” in Kerouac’s “The Dharma Bums”). He died in Santa Barbara in 1982, spending his last years translating the works of Chinese and Japanese women poets.

Max Bodenheim, the king of bohemia, was shot to death in a New York flophouse in 1954.

A 62-year-old homeless alcoholic who routinely beat his 35-year-old prostitute wife, Bodenheim and the former Ruth Fagan had been offered a room in a $5-a-week hotel by a 25-year-old dishwasher named Harold Weinberg.

“The poet whose fine poems once infuriated critics, embittered editors, estranged readers and earned him, nevertheless, a curious sort of fame,” as Hecht once wrote, woke up from a pass-out drunk to find his wife and host fucking. He attacked Weinberg, who shot him in the chest before stabbing Ruth repeatedly in the back.

“I ought to get a medal. I killed two Communists,” Weinberg told police after the manhunt. He was sentenced to an insane asylum.

Hecht, who published his autobiography to commercial and critical success that same year, sent a little money to help pay for Bodenheim’s funeral. No one claimed Ruth’s body.

Hecht died in fame and fortune a decade later.

And now we have an alley.

It’s an alley in a ritzy street where the homes cost a couple million a pop. It’s an alley where chain link protects both crossovers and lanky men calling to their wives for barbecue supplies. It’s an alley where the only signs of revolution and revolt are scribbled hastily on Dumpsters.

It’s an alley where there was once an orange door.

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