The thing outsiders know about Chicago is crime. The mobsters, the street drug gangs, the corrupt operators—these are the most sensationalized aspects of the city. But they are also key factors in its ongoing narrative, the one true Great American Novel that is Chicago. The city with a fiery creation myth grew into a blue-collar metropolis with the help of oily, feudal political machines and assorted local species of crook, leaving a deep, ugly legacy. It is written in our street grid, our transit lines, and our segregated accents, in which one can still hear both the old white ethnic strongholds and the Great Migration. It can be a very beautiful city, especially at night. In those icy parts of winter that have become more rare since I first moved here, the unique nighttime color of Chicago reflects in every direction. The flatness of the landscape and the straightness of the streets bring its divisions into deep focus. I’m proud to show it off. It is a city on the prairie, and therefore a city of the plain, like Sodom and Gomorrah in Genesis.
For a time in the 1850s, there were so many problems with drainage that it became a swamp and had to raise itself up on jackscrews. So really, a Chicagoan has their pick of origin stories. The curse of the so-called Second City is that it lends itself effortlessly to symbolism and especially to metaphor, to the point that you start to believe that it just might be one. I’ve lived here longer now than I have anywhere else, and I have come to love this aspect of the city. When Chicagoans speak—whether they are true locals or transplants like myself, who have come to its ways through prolonged exposure—they speak its complicated history. This is the diverse Southern-inflected sound of black Chicago, the “Chi-cah-go” and “Chi-caw-go” pronunciations that classify white accents, and that perfect formulation of terse Midwesternese, the stranded “with,” as in the classic “You wanna come with?” They say “jagoff” is a Pittsburgh word, but Chicago owns it.
Really, there are many Chicagos, bound almost psychically. It is better maybe to try to grasp it in terms of its architecture—which is really one of the most beautiful things about it—and planning. For instance, Chicago is the alley capital of the world. There are about 1,900 miles of alleyways running through almost every block of the city, regulated to a minimum width of 16 feet, some much wider. The alley is part of day-to-day life in Chicago: It’s where we take our shortcuts and bring our trash. It’s why Chicago doesn’t smell as bad as other big cities. It lacks that note of garbage that gives New York streets their character. The kind of buildings we call two- or three-flats, whether brick, frame, or Indiana limestone (called “greystone” locally), will often have a gangway, a passage that lets you cut from the sidewalk to the alley. My favorites are the ones that dip under a protruding oriel. And most of the apartments in those two- and three-flats will have two doors, one in the front and one in the rear. It’s a city of backstreets and backdoors.
Chicago crime is a unique phenomenon. In broad statistics, it is not that dangerous a place; the rates of burglary and theft are low for an American city, and many of its neighborhoods experience negligible violent crime. This is a common defense tactic for Chicagoans, especially white Chicagoans—the “well, not my Chicago” plea. But this is as much a fantasy as the Trumpian burning of the quote-unquote “inner city.” Chicago crime inspires fascination because it is entrenched and so specific, so troublingly connected to a diverse city that otherwise eludes broad social generalizations. One fact about Chicago is that it has more nicknames in common circulation than any other place in this country, all of them kind of tacky: the Windy City, the Second City, Chi-Town and its pun variations, the City Of Big Shoulders. There are many others, too. Defining the spirit of Chicago is a bad parlor game. The nice parts of it are very nice, but for more than 90 years, it has been world-famous as a place where people get gunned down in the street. Throughout its history runs a succession of criminal boom industries: gambling, policy, liquor, crack, heroin.
The criminal conglomerates of Prohibition and the small sets of the West Side’s Heroin Highway are part of one uninterrupted story, though unwittingly. The story is the city. It goes back to the 1870s and the reign of “Big Mike” McDonald as the king of Chicago’s gambling underworld. It goes through generations of increasingly more effective political machines and increasingly larger criminal syndicates, colluding in political and commercial networks that made the street gangs seem like the inevitable result of a complicated equation. Let us assume a few things here as starting points: that the city and its underworlds have existed for a long time in a relationship that is more complex than host and parasite; that political and criminal groups in the city, however big or small, play variations on a similar game involving the flow and direction of movement; and that the city is itself a crossroads, its entire story defined by lines of interstate transit, be it the Illinois Central Railroad that transported half a million black job-seekers from the South during the Great Migration, or the Sinaloa Cartel network from which most of the cocaine and heroin of its current drug economy is believed to originate.
For Chicago, there is no artistic or cultural history without its social history, no social history without its political history, and no political history without crime. The mob is a staple of our tourist kitsch industry: the Al Capone T-shirt and the Untouchables bus tour, right up there with Mike Ditka’s hairspray, the goddamn Blues Brothers, and that casserole we call a deep-dish pizza. But the mob was always corny, even at its scariest. For decades, it was almost everywhere. I’ll give you an example: The Russian bathhouse immortalized by Saul Bellow in Humboldt’s Gift was actually a mob hangout. It was still owned by an Outfit family in the years that I lived across from it on Division Street, one of the more darkly perfect street names in Chicago.
Act I
Mothers, don’t let your babies grow up to be mobsters
Michael Mann’s 1981 debut feature, Thief, is to my mind the best Chicago crime film set after Prohibition and one of the great artistic interpretations of the city’s nocturnal character. It was made in the last years that Chicago nights glowed bluish-green, before the city had completed the changeover from mercury vapor lighting to the sodium vapor lamps that produce its present honey-bronze haze. Much as alleyways have both a practical and a mystical relationship to the city’s networks of crime, so it is possible to chart eras of criminality through the history of its public lighting. Crime is a largely nocturnal activity, after all, as are most of the vices on which the city’s criminal syndicates were built. In the Prohibition and Great Depression golden age of Chicago crime, most of the streets were still gas-lit and very dim. This was the fabled era of the Tommy Gun mobsters, but also of the bank-robbing outlaw, embodied by the Chicago-based Dillinger Gang, the subject of Mann’s underappreciated crime epic Public Enemies. Mercury vapor arrived in the mid-1950s, along with Richard J. Daley’s Democratic political machine and the solidification of the Chicago Outfit, the white mob, which in those years finally murdered and intimidated its way into the territory of the city’s forgotten black crime syndicates. The most recognizable type of streetlight in Chicago was introduced in this era. It’s a bucket-shaped design unique to the city, called the General Electric Crimefighter.
Thief is not a film about the Outfit, but it features an Outfit operative as a character, played by the avuncular stage veteran Robert Prosky. You have probably seen a picture of Al Capone. Chances are it’s the glamour shot with his head turned and the cigar stuffed in his cheek and the size 6 7/8 cream-white Borsalino on his little head. This is the most flattering picture of Capone. As a young man, he had the pudgy face and baggy eyes of a fortysomething bank manager. He was 26 when he inherited Johnny Torrio’s criminal empire and was out of power by the age of 33. But in movies and TV, he is always played by older actors, trimmer or more barrel-chested, always tougher-looking than the real man: Rod Steiger in Al Capone; Neville Brand, Robert De Niro, and William Forsythe in successive versions of The Untouchables; Jason Robards in The St. Valentine’s Day Massacre; Stephen Graham on Boardwalk Empire. But there were never any handsome gangsters. They were all funny-looking, and with the exception of the flashy Capone years, they dressed like shit.
The Outfit was the successor to Capone’s organization, and in that era of mercury vapor lighting, when the tint of the night suggested an extended twilight, their look was Sansabelt, grandpa glasses, and starched short sleeves. Mann grew up in the long-gone Jewish quarter of the Humboldt Park neighborhood, as did Saul Bellow a generation earlier, and he is one of the few to try to capture this banal, used-car-salesman aspect of the Chicago mob. To me, he is one of the geniuses of the genre; in all of his crime films, there is a complex dialogue between authenticity and archetype. His favorite type of verisimilitude is the kind that directly contradicts expectations. In Thief, for instance, the safe-cracker played by James Caan—the first of the single-minded professionals that would become Mann’s contribution to the mythology of the crime genre—doesn’t press the resonator of a stethoscope against a door and listen to the tumblers; he uses an industrial oxygen lance, lent to Mann by an actual Chicago-area burglar. And while Prosky’s role might seem like a case of casting against type, if you look at pictures of Outfit bosses from the time, that’s what they all looked like.
But here’s the thing: The imagery Mann subverts with this more realistic portrayal—and uses to formulate his own mythology—is also Chicagoan in origin. It was Chicago that birthed both the gangster picture and the notion of street criminal chic, and it really took until The Godfather for there to be a major American film that took its cues from the clannish organized crime culture of the East Coast. Even the great New York gangster movies that came before The Godfather, like Raoul Walsh’s The Roaring Twenties and Budd Boetticher’s The Rise And Fall Of Legs Diamond, are based on an archetype born of the Second City. Most film historians will tell you that there are two definitive early gangster films: Underworld, directed in 1927 by Josef Von Sternberg, and Howard Hawks’ insurmountable 1932 Scarface. Both are set in Chicago, as were almost all early American gangster movies—Little Caesar, The Public Enemy, the whole lot. The gritty city stuck in the imagination of ’30s Hollywood much in the same way as Paris and Vienna did, less a real-world setting than a genre in and of itself. Films about criminal gangs go back to the early 1900s, but they depict their bad guys mostly as ragged, unshaven goons in flat caps. The seductive criminals of the silent era are swindlers and masterminds. The idea that coarse, murderous thugs could be flamboyant, magnetic, and sexy—that comes from the Chicago of Al Capone and John Dillinger.
Both Underworld and Scarface were based on stories by Ben Hecht, though the latter was nominally adapted from a forgotten pulp novel of the time. Before he became one of the greatest screenwriters in the history of Hollywood, Hecht was a Chicago Daily News crime reporter, an experience he would draw on many times—most famously in The Front Page, one of several collaborations with his crime-desk colleague Charles MacArthur, subsequently reworked as His Girl Friday. Hecht was one of a number of literary men who worked in the Chicago dailies of the 1920s (the poet Carl Sandburg was also at the Chicago Daily News at the time), and the best of a tradition of newspapermen who treated the job of columnist as though it made them prose-poet laureate of Chicago. A reader of modernist and symbolist literature, he was also involved in the Little Review, the Chicago literary magazine famous as the first publisher of James Joyce’s Ulysses, which was originally serialized over several years in its pages. In Underworld, released at a time when Joyce’s landmark novel was still banned as obscene in the United States, there is a villainous Irish gangster named Buck Mulligan, after the central character of the first chapter of Ulysses—a fact that I’ve always found amusing.
The classic, Hecht-ian gangster drew on the public’s morbid fascination with Chicago crime to create something almost modernist—this wanton criminal as an epic figure in an expressively metaphorical cityscape. This is true of Scarface, a masterpiece that was the work of a number of remarkable talents, not just Hawks and Hecht. One of the many memorable things about Scarface is the use of signage as commentary and ironic counterpoint: the famous “The World Is Yours” travel ad (carried over in Brian De Palma’s loose 1983 remake); the body lying under the crossed shadow of a signboard that reads “Undertakers”; the lit-up marquee of the club called “Paradise No. 2.” The Godfather would refashion the gangster as a creature of family and loyalty, but in his original conception, he was a creature of the city. Scarface’s Capone-inspired title character doesn’t rise to power in the middle of nowhere, but in a darkly comic metropolis that seems to empower and mock him in equal measure. In other words, he rises to power in Chicago.
It should be pointed out that almost all Chicago-set Hollywood films produced from the late 1920s to the 1970s are about mobsters, crime, or corruption. We’re talking Nicholas Ray’s Party Girl, assorted half-remembered noirs, various versions of the Roxie Hart story (including one written by Ben Hecht), the premise of Some Like It Hot. Of these, only Arthur Penn’s Mickey One, the film that first attempted to apply a French New Wave sensibility to home-grown pulp, did any substantial filming here, capturing both its decrepit alleys and its modernist architecture in stark black-and-white. It was only in the 1980s that the city became a popular filming location. Perhaps Thief seems definitive because it represents a point of merger—between the mythology of the city and its reality, which already seems fairly stylized.
Figuratively and literally a city
The great musical legacy of Chicago is the modernization and urbanization of the blues, a rural sound that was electrified by the city and laid the groundwork for most popular music that has come since. One important but underappreciated figure in its development was Kokomo Arnold, who played a rapid bottleneck-slide-guitar blues in a style that still sounds rock ’n’ roll. It is said that he came to Chicago as a bootlegger in the 1920s, but was forced to rely on his musical talents for a living after the end of Prohibition, trading one business of handling bottles for another. However, when it comes to stories about bluesmen, one can never be sure. Arnold’s recording of “Old Original Kokomo Blues” was reworked by the Delta bluesman Robert Johnson into “Sweet Home Chicago,” now the de facto anthem of the city. “Sweet Home Chicago” isn’t actually about Chicago. It uses the name of the city figuratively. It has to be the most singable place name in American English: Chi-ca-go, those three syllables, each ending in a different vowel sound. It lends itself to varied interpretation.
More so than any place in America and perhaps even the world, Chicago was founded on the idea of a city; before it had developed a cultural life of its own, it was a word, a notion, and a destination, ballooning over the second half of the 19th century from a smallish midland settlement into what was then the fifth largest city in the world. It is a place that inspires ideals—from the Wobblies to the aesthetic of Afrofuturism, the Hull House to the tradition of philosophizing architects embodied by Louis Sullivan, Daniel Burnham, and Frank Lloyd Wright. But how much of Chicago’s idealistic streak is a reaction to its cynical pragmatism? For as long as it has deserved to be called a city, Chicago has had problems with disenfranchisement, corruption, and crime—problems that seem like they were almost designed into the city. I’ll point out here that in his Whitman-esque poem “Chicago,” which is the source of the nickname “the City Of Big Shoulders,” Carl Sandburg also writes: “Yes, it is true I have seen the gunman kill and go free to kill again.” And this is the definitive celebration of the city.
It was Nelson Algren who mastered the art of making Chicago’s seediness sound like an exotic quality. He is best known for his novel The Man With The Golden Arm, which is set on that same mythologized stretch of Division Street that was home to Saul Bellow’s Russian bathhouse. Here, I’ll point out that Otto Preminger’s well-known 1955 film adaptation, starring Frank Sinatra as a heroin-addicted jazz drummer, was co-written by an uncredited Hecht, because everything somehow intersects in the novel of Chicago. It opens with a prowling long take down an evocative soundstage street that bears only a faint resemblance to the real city. It’s a Chicago of the imagination, but so are most. In his essay “Chicago: City On The Make,” published two years after The Man With The Golden Arm, Algren gave the city one of its most famous panegyrics: “Like loving a woman with a broken nose, you may well find lovelier lovelies. But never a lovely so real.” Like so many Chicago transplants who came here in the mid-2000s to lead a quasi-bohemian existence, I have this passage memorized. But it did not occur to me until many years later to ask who broke the woman’s nose.
The fact is that, while the crime and corruption provide links between Chicago’s countless neighborhoods, their effects have always been graded by skin color. I know of no black writer of the same periods who wrote of Chicago crime as a sign of its resilient spirit, as Sandburg did, or as an Algren-esque existential quality, the proof of its hustle—not even Iceberg Slim, who was second only to Ben Hecht in developing and popularizing the mythology of the street criminal. Slim—who was born Robert Maupin, but took Robert Beck as his legal name in middle age—had been a dapper pimp in the black underworld of Chicago and the upper Midwest in the 1940s and 1950s, until a breakdown in the Cook County Jail led him to retire. He had been known as Cavanaugh Slim. It was while working as an exterminator in Los Angeles that he wrote his autobiographical novel Pimp: The Story Of My Life, a bestseller that would come to define the voice of gritty urban pulp. Along with his subsequent crime novels and the follow-up memoir The Naked Soul Of Iceberg Slim: Robert Beck’s Real Story, it would exert a profound aesthetic and thematic influence on gangsta rap, blaxploitation films and black variations on noir (Bill Duke’s Deep Cover, for example), and the prose of a vast array of fiction writers, most notably Donald Goines and Irvine Welsh.
Slim was a complicated figure. Like Chester Himes, the godfather of black noir, and Ed Jones, the most powerful black kingpin of Slim’s early years in Chicago, he had a go at a respectable college education before lapsing into crime—though, admittedly, he already had a lengthy rap sheet by the time he arrived at Tuskegee, where he was a student around the same time as Ralph Ellison. As a prose writer, he was ecstatic and contradictory, the king of mixed metaphors, capable of lucidly deconstructing the misogyny and self-loathing of his criminal past one moment and juicing readers with lurid sexual exploits the next. Like Hecht, he sculpted the seductive aspect of Chicago crime—but in place of the classic gangster film’s anti-social pizzazz, what he presented was a cool, toughened nihilism. Perhaps Slim came to believe his own legend. After he found recognition as a writer, he adopted the public image of a wocka-wocka mid-1970s pimp, though his own heyday had been in the days of boogie-woogie and parted hair.
Indulge me now and take a moment to listen to “County Jail Blues,” a 1941 B-side by the Chicago blues pianist Big Maceo Merriweather. It’s an ageless song, and, in my opinion, one of the great overlooked blues recordings of the 1940s. The guitarist is Tampa Red, who played a gold-plated steel-body guitar that sounds remarkably like an electric. In its ideal form, blues is not glamorous music.
Act II
Dromocrats of early jazz
The cultural legacy of Chicago crime is really two stories, but they are intertwined. The first is a story of myths, plucked from the streets and alleys of the city and fermented in the popular imagination. The second is a complex narrative of devil’s bargains between art, business, political machinery, and crime. It stretches from the brothels of the early 20th century to the super-sized media conglomerates of the present day. Let me relate one small part of it.
The first black millionaires in America were probably policy kings, most likely in that densely populated area of the South Side that was then known as the Black Belt. Policy was an illegal lottery in which winning numbers were drawn from policy wheels (often rigged), which in Chicago bore such names as the Airplane, the Kentucky Derby, and the Prince Albert. It was a huge enterprise, with each wheel having its own drops, runners, and policy writers—not to mention a whole sub-industry of numerologists and hucksters who called themselves “policy professors” and hawked dream-based winning formulae in the ad pages of the Chicago Defender. If you want to try to get a sense of the spirit of the time, take a listen to “Four Eleven Forty-Four,” by Papa Charlie Jackson, the sardonic, banjo-playing chronicler of life in Chicago’s black neighborhoods in the 1920s and the first commercially successful self-accompanied blues musician; the title is the prototypical number combination, or gig, and a byword for policy itself.
The great policy kings are mostly forgotten now: Policy Sam, Mushmouth Johnson, Teenan Jones, Ed Jones (no relation) and his brothers, Dan Jackson, Teddy Roe. But their influence on the economic and political life of the city can’t be overstated. For the first half of the 20th century, the white powers that be considered them essential to the black vote in Chicago. When it comes to this city’s history, one should probably always think cynically and feudally: a community where the largest local employer, voter registration effort, charity, and source of capital is a single criminal racket is a corrupt administrator’s dream. Political machines gave policy kings leeway to keep them in power. During their reign, the center of black nightlife in Chicago was a section of the Bronzeville neighborhood known as “The Stroll.” How perfect is that, in a city where control is synonymous with directing movement?
The 1920s and ’30s were Chicago’s heyday as a center of jazz talent and innovation. One of the most important clubs of this era was the Grand Terrace, known in its early years as the Sunset Cafe. The building—originally a garage, and until recently a hardware store—still stands on 35th Street. This was where Louis Armstrong became a star with a teenage Cab Calloway as his master of ceremonies, where Nat King Cole got his first break, and where the trailblazing pianist and bandleader Earl “Fatha” Hines had his 12-year residency, playing a piano bought for him by Al Capone. In the ’30s, the Grand Terrace had its own national radio show, broadcast live every night. Policy kings owned many popular clubs on The Stroll, including Palm Tavern (owned by Genial Jim Knight) and the Elite No. 2 (owned by Teenan Jones), which I’m almost certain inspired the similarly comical name of Scarface’s Paradise No. 2. But the most lucrative and glamorous spots were integrated black-and-tan clubs like the Grand Terrace and the Plantation, which was located across the street. Both were controlled by the Capone organization through Jewish associates.
Unlike the Outfit that succeeded him, Capone made a point of leaving the black syndicates alone. There were many reasons for this, including the fact that the mob and the policy kings were both colluding with the Republican political machine headed by Mayor William H. Thompson, a flagrantly corrupt figure who believed that the one true enemy of America was the British crown. But the one that matters here is the mob’s intended audience. The Grand Terrace attracted many wealthy black customers, from bona fide celebrities to local crime lords (Icerberg Slim’s mentor, “Baby” Bell, spent there lavishly), but it was designed to draw in white money. Anyone who wanted to make a career in Chicago had to play the mob’s segregated circuit. The white jazzmen (including such talents-in-training as Gene Krupa and Benny Goodman) mostly played whites-only venues, while the black jazzmen played black-and-tan clubs, where white musicians could sit and play if they wanted. The privilege did not go the other way around.
Thus, the mob invisibly controlled the direction of musical influence, as it did so many other things that may seem intangible. Its monopoly on early Chicago jazz had many consequences, one of which was an eventual exodus of talent, beginning with the great cornetist King Oliver, who led the band at the Plantation Café. Oliver was a true tragic figure; he gradually lost his teeth and the ability to play to severe gum disease, ended up working as a janitor in a pool hall, and died broke in a rooming house. In the mythology of jazz, his downfall into obscurity and fatal poverty is all the result of his refusal to take a lowball offer for a regular gig at the Cotton Club, which instead catapulted Duke Ellington to stardom. This is the thing to remember: Much of the formative 1930s period of jazz, a music with deep black roots, happened on terms set by white criminals. After the black-and-tan clubs went out of fashion toward the end of the 1930s, the Chicago mob got into coin-operated jukeboxes. Thankfully, they never developed an interest in blues.
Regardless of age or gender, Chicago will turn you into an old man giving directions. Every story reminds of another story, and a story of something that used to be there—because it’s really all one story. After the Outfit took control of policy and bolita, a similar numbers game popular in the city’s Latino neighborhoods, they became absorbed into the gambling and vice empire of the Rush Street crew, whose day-to-day manager went daily to Saul Bellow’s beloved Russian bathhouse on Division Street. The Grand Terrace, having finally gone out of business, became the headquarters of the Democratic congressman William L. Dawson. He was the black sub-boss of Chicago’s political machine, and, in theory, the most powerful black politician of the 1950s. He didn’t redecorate the Grand Terrace. It still had its big neon sign (with a smaller sign with his name added) and its Jazz Age murals and private upstairs clubrooms. The last regular bandleader at the Grand Terrace had been the jazz iconoclast Sun Ra, who was then just developing his sci-fi aesthetic in Chicago.
Dawson’s position within the political machine was a feudal lordship; it was dependent on his ability to bring out black voters en masse. The political machine, in turn, depended on segregation and on interchanges with the underworld. The link between the Outfit’s earlier inroads on The Stroll and the Democratic political machine’s command of the post-war black voting block was made literal and blatant by the continued use of the Grand Terrace. There, Dawson’s landlord was Joe Glaser, the manager of Louis Armstrong and Billie Holiday and a longtime Outfit man. Glaser, who had an early history of walking away from sexual-assault charges, had been a boxing promoter who specialized in fixing fights for the mob and then a manager of black-and-tan clubs. After the repeal of Prohibition destroyed the Outfit’s stranglehold over Chicago liquor, he would rob delivery trucks to stock the bar of the Grand Terrace.
The management company Glaser created—and willed to the Outfit lawyer and power broker Sidney Korshak, unbeknownst to Armstrong—was funded by a loan from Jules Stein, an ophthalmologist, former bar mitzvah musician, and jazz booker for the Chicago mob circuit. Stein’s booking company was MCA, which started with speakeasies and black-and-tan clubs and became the largest talent agency in the world by the end of 1930s, all while being effectively controlled by the Capone organization. It acquired Universal Pictures, and expanded beyond talent management into film, television, music, and publishing. It kept its ties to the Outfit and carried over the city’s culture of patronage to Hollywood, where it encouraged the political ambitions of its client Ronald Reagan. At the start of this century, it merged with Vivendi to create NBCUniversal and Universal Music Group. This is the story of the Outfit controlling who worked in one building in Chicago. It’s a big city. There are many buildings.
Act III
The moon in sodium vapor
If you are ever in Chicago, consider taking a drive through the city at night. Let the car rattle on the badly pockmarked streets. Your eyes will adjust to the amber sear of the General Electric Crimefighters and to that other feature of Chicago nighttimes, the blue flash of a police camera box. There are thousands mounted around the city. Turn down an alley and think of the fact that even in the earliest plat of Chicago, dating to the 1830s, there were plans for alleyways. Park the car, get out, and study how the dimensions and alignment of the streets and sidewalks affect your movements. Don’t think of crime as troglofauna, pale and eyeless, evolving in the dank corners of the city. In Chicago, crime moves, often along currents defined by earlier forms of crime. It’s structural.
Given that they have brought Chicago its most sensationalized coverage since the days of Al Capone, it seems interesting that there have been no real fiction films about the street gangs. Spike Lee’s Chi-Raq doesn’t count. Its portrayal of Chicago’s gangland is pure fantasy, influenced by the mythology of gangsta rap—which is to say, indirectly indebted to Iceberg Slim. Even in fiction, the city can’t escape the myths it inspires. You could say that about drill, our distinctive midtempo flavor of nihilistic trap rap. Drill tends to be oversimplified as the authentic sound of modern Chicago crime, which is how it sells itself, existing as it does in a complicated relationship with the histories and ongoing conflicts of Chicago’s drug gangs, grouped in the increasingly meaningless six-pointed-star Folk and five-pointed-star People alliances.
Really, drill is internet music. It owes its local significance, popularity, and very existence to limitless digital space and social media. Drill is the dizzying, exhaustive braggadocio of Montana Of 300’s “Holy Ghost”; the squishy nausea of Lil Durk’s “Glock Up”; and the hammering of Chief Keef’s “I Don’t Like”; but it is also a thousand guys who can’t rap boasting about the same shit over $50 beats while hustling for Instagram followers and YouTube views. Quality drill albums are nonexistent, and consistent drill mixtapes are rare as hen’s teeth; the ratio of filler to killer is notoriously poor. The mise-en-scène is remarkably consistent from video to video: guns; unimpressive cars; alleys, gangways, and iron gates; ugly weather; those hideous kitchen cabinets that seem to have been installed in every Chicago apartment, regardless of neighborhood. But cheapness and a lack of inspiration are part of the authenticity factor, because drill is immediate. It’s also on the outs, having never crossed over the way that the Savemoney scene made famous by Chance The Rapper and Vic Mensa has.
Nowadays, Chicago crime is defined by the street sets, mostly black or Latino, related by business and varying adherence to the mythology of the gang, prone to violent infighting and splintering. What makes this underworld special is that most of its artistic record is self-produced. These are the patch-sewn cardigans and calling cards of the old-school 1970s street gangs; the outsider literature of the Gangster Disciples’ manuals, more cultish than criminal; the hieroglyphic symbolism of the gang tags that cover Chicago’s alley-facing garage doors; meandering amateur movies in which people pretend to shoot each other with real guns; drill. Despite the early ambitions of the Vice Lords and the Latin Kings organizations, the street gangs have only ever been politically useful as bogeymen. By most estimates, there are around 100,000 street gang members in Chicago, divided into about 60 organizations that are in turn split into about 700 groups. Not every Chicago gang is a violent criminal enterprise, but the majority of murders in Chicago are gang-related, and most of them go unsolved.
There is nothing transgressive about our gangs. Chicago is a place where one can always map the relationship between the criminal and the city. It taught the world that the street criminal could be a charismatic figure and inspired a mythic bestiary of genre archetypes: the terse Mann-ian professional facing obsolescence; the mobster gunning for the throne of the city; the nihilist pimp who knows it’s all part of the game; the folk-hero bank-robber shot by lawmen in the back; the corrupt and colorful wheeler-dealer. But the street gangs can’t be understood on those terms. To an outsider, their public beefs can sound like the sectarian conflicts of a post-apocalyptic religion; witness the bloody feud between the Bang Bang Gang Terror Dome subset of the Black P. Stones and the New Money Killaward subset of the Gangster Disciples, which in 2015 caught the attention of a city otherwise desensitized to the idea of gangland murders.
The ongoing social tragedy of murder in Chicago isn’t that there are so many (there are a lot, but it’s never ranked among the top American cities in that respect), but that they are so similar, the same m.o. repeated over and over again. It can reach the point where you almost trick yourself into thinking of the urban gangland as an organism or serial-killer hive mind. But it isn’t. The foibles of the street gangs are very human. And, though we don’t like do admit it, they are relatable.
The French novelist Jean-Patrick Manchette liked to call crime fiction “the great moral literature of our time,” a statement I sometimes find myself agreeing with. There is no more efficient way of putting a character in a moral and existential crisis than a crime, and it is a dark truth of every developed society that, regardless of circumstances, we are all capable of committing a heinous crime. The question of why some do while most don’t directly addresses an important piece of the human puzzle. But in this chapter of the ongoing story of sin in Chicago—the story as told in film, in music, in the media—crime has become a setting, a fact of the neighborhoods, not a question of personalities. No documentary about the day-to-day lives of street gangs (and there are a lot of them, made mostly for TV) has had the wider appeal of Steve James’ Hoop Dreams or The Interrupters—though, of course, none of them are as well made. This is a net positive.
But let me posit something that may seem counterintuitive. It isn’t a plea for a return to romanticized crime, though I do think that the forbidden lure of the illegal and immoral can be subverted in powerful ways; it’s something many of the great crime narratives do. But I do think that the art that most cogently addresses crime—whether as a real-world social issue or as an existential state—is art about criminals, because it puts its audience in a compromised spot. There is something of a moral duty to resist the othering of crime. When we begin to think of gangs exclusively as a social phenomenon, instead of as people in groups, we dehumanize not just the gangs, but the people they exploit and victimize, a category that includes the gangs themselves.
One of the more often cited example of this is the 1992 horror film Candyman, which places a supernatural threat within the crime-infested projects. (If you have the time, I recommend watching our short video documentary on the film.) It’s set in Cabrini-Green, which was then the most notorious housing project in Chicago; it was also the home of one of the subjects of Hoop Dreams, the setting of the ’70s sitcom Good Times, and the subject of several documentaries of its own. Candyman is a film that raises some interesting ideas early on, but waffles on them. In the end, it falls back on that all-too-popular image of the urban gangland as a monster, a variant of what one might call the second curse of Chicago—the idea of the city itself as an abstract threat. But it’s always people. Cabrini-Green is gone now, long demolished. In Chicago, it was symbolic of controlled disenfranchisement: a 15,000-person enclave of poverty in an affluent area. The street that ran directly down the middle of the complex—well, you can probably already guess this one. It was Division.