Rebellious Space and Radical Movement: The Dil Pickle Club of Tooker Alley

In July 2022, I spent the warm, windy Chicago days in the Newberry Library’s air-conditioned archives, poring over stacks of photographs, drawings, notes, letters, and broadsides related to the city’s famous Dil Pickle Club. Conceived as a bohemian enclave in the midst of Chicago’s aesthete-minded Tower Town, the Pickle was a pillar of the Chicago Renaissance, a speakeasy that Marc Moscato has called “one of the most creative, politically engaged and influential American cultural centers of the 20th Century.” As I familiarized myself with the Pickle’s world—its events, publications, and people—I felt that I needed to see the space for myself. After all, its former location between Dearborn and State Streets is quite near the Newberry. As I walked down Tooker Alley on a Thursday afternoon on my lunch break, I didn’t know what I expected to see, but I expected to see something. But when I arrived, all I saw were brick buildings and a bit of detritus littered on the backstreet—there was no sign of the Pickle at all.

Rather than discouraging me, the Pickle’s absence piqued my interest in the club’s physical space—a space that accommodated Chicago’s revolutionaries, anarchists, and bohemians. We’ve likely all heard the phrase “What’s in a name?” even if we must search the depths of our high school English class memories to recall who said it. But how often do we ask, “what’s in a space?” Undoubtedly, if applied to the Pickle, either of these queries would lead the inquirer down a path of extensive, complex, and entertaining discovery. Let’s be honest, “Dil Pickle Club” is a pretty appetizing name. But the Pickle’s physical space is just as intriguing. More than a passive backdrop to the club’s activities, the space actively contributed to its rebellious ethos, from the dark, smoky, jam-packed lecture room that housed up to 700 people to the interior platform walls, which were covered with paintings of varying quality.

For the origin of the Dil Pickle Club, we have to go back to 1914. John “Jack” Jones, a former union organizer and proud “Wobbly,” initially established the Pickle as an amorphous, spaceless weekly gathering where individuals discussed social and labor issues. In 1917, Jones gave those nomadic meetings a brick-and-mortar home that fundamentally retained their ethos and energy while providing a mingling space for a transnational collection of radicals, anarchists, leftists, and artists. For Jones, this club served as a “center where any idea or work would be given a respectful hearing and brought before the public, which… are the best judges of what they want.”

Even among progressive, left-leaning, Chicago Renaissance communities, the Pickle stands out as arguably the most radical and egalitarian. With the likes of Emma Goldman, Lucy Parsons, Carl Sandburg, Mary MacLane, Djuna Barnes, Lawrence Lipton, “Queen” Elizabeth Davis, Jun Fujita, Sherwood Anderson, Ralph Chaplin, Katherine Dunham, Kenneth Rexroth, Sam Dolgoff as everyday attendees, Dil Pickle regulars—or “Picklers”—did not frequent the club for its food and drink specials. In a 1919 advertisement printed on July 18 in The Chicago Daily News, Sherwood Anderson beckoned those with revolutionary ideas to visit the Pickle and participate in its liberal, open exchanges:

Are you a struggling poet, groping your way through a dark and dreary commercial world? Have you written a prose masterpiece that some money minded publisher will not publish? Are you an eager young feminist, longing to lift womanhood into the higher life? Have you painted or sung or sculpted or thought something that the dull minded world does not appreciate…Jack Jones and the Dil Pickle are looking for you. 

Anderson’s opening volley of questions is a call to action: he speaks to readers who dare to challenge convention and provokes them to “do” something with their innovations. These provocative inquiries capture the ethos of the Pickle and position the club as a space for evolution and creation. This is all to say that the Pickle’s concept was unique even amongst Chicago Renaissance hotspots, bringing drifters, rabble-rousers, pacifists, thieves, medical doctors, and university professors together to have both weighty and frivolous conversations while drinking cups of hot tea or soft drinks because prohibition forbade the selling of alcohol.

Space, movement, and revolution coalesce in the Pickle and begin at its entrance. The club—described as a shabby, cleared-out barn—was located at 18 Tooker Alley, near the Radical Book Shop and the Newberry Library. However, as I found, it was barely visible from the street and quite difficult to locate without prior knowledge. To find the club, perspective entrants were instructed to wedge themselves “Thru the Hole in the Wall Down Tooker Alley to the Green Lite Over the Orange Door,” a sentiment echoed by anarchist and physician Ben Reitman, who describes the odd, uncomfortable experience of having to “squeeze down a narrow passageway between the Dil and its neighboring building.”

Entering the Pickle was also an unusual experience and required a certain amount of dexterity and spatial creativity—a fact cheekily acknowledged by the the inscription “Step high, speak low, and leave your dignity behind” emblazoned on its front door as well as the painted “Danger” sign directly above the frame. Danger indeed: Picklers needed to climb a rather high stair through the slight, dimly-lit threshold, then slump downward just to enter. It seems that only individuals who desired to engage in rebellious spatial movement—for instance, to disaffiliate from the sidewalk and contort their bodies—earned their passage into the Pickle and the opportunity to partake in the club’s radical conversations.

After a period of financial strife, The Dil Pickle Club of Tooker Alley officially closed its doors in 1934. The eclectic, egalitarian bohemian club between Dearborn and State Streets is now a vacant place, an unassuming brick building bordered by a few dumpsters that gives no clue or homage to its legacy. In a fascinating twist, those who are looking for the Pickle’s former location still must have prior information and familiarity in order to find its empty shell. During its near two-decades long lifespan, the Pickle was a place of movement, progress, and generation—an intersectional space that, progressively for its time, showcased the diversity of Chicago’s political left and welcomed minorities and marginalized populations. The  “spirit” of the Pickle, however, did not perish with its physical space. Moscato began a now-disbanded Portland, Oregon-based discussion group named after the club, and its ethos continues to captivate individuals who are “in the know.” So I ask again, what’s in a space? For the Dil Pickle Club and its diverse attendees, a space is everything and nothing: an entity that, through rebellious motion, facilitates radical movements.

Elysia Balavage is an Anisfield-Wolf Fellow at Case Western Reserve University researching the intersection between transnational modernism and philosophical nihilism as well as literary representations of working-class food culture in interwar Britain. Her work appears in the Review of English Studies, the Journal of Modern Literature, and Modernism/modernity, among others. Twitter: @balavage_elysia

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