Normally, Jeff Fort didn’t yield to authority. Especially not to the white teachers at Hyde Park High School. They constantly harassed the teenager. When white teachers commanded him to take off his hat, Fort would retort, “Jeff Fort ain’t gonna obey.”

But the student and his crew did listen to Timuel Black, one of the few black teachers at the high school in the early 1960s. “We were like their daddies,” Black says. “They respected us.” So when Black stopped Fort in the hallway and ordered him to take off his hat, Fort respectfully removed the cap from his bush-top head.

Fort, the Blackstone Rangers and future P Stone Nation leader, didn’t quite fit in this milieu on the South Side of Chicago. Hyde Park High School was an elite place for University of Chicago professors to send their children. Black said the school, located at 62nd and Stony Island, engaged in conspicuous tracking of its white and black students. The administration appeased white parents by creating so-called elite tracks for their students. And white troublemakers stayed in school while any infraction got black kids the boot.

Fort would’ve been considered a troublemaker. A fearless tough guy, Fort told the jokes but didn’t like any turned on him. He was a short, slender teen who carried himself as if he had the physique of a professional bodybuilder. And while the lore around Fort is that he’s illiterate and never made it past fourth grade, Black contends that “he could not read at the level he should have been reading, but he could read.” And though “he was not by any means a scholar,” the pupil had other gifts, leadership qualities that were intangible, difficult to describe. Black said the charisma often ascribed to Fort was obvious in his adolescence. He was not just another rough boy from the neighborhood with low grades.

When Black approached Fort to ask, “Hey, boy, you want to stay in school?” Fort replied, “Yeah, but they are always picking on us.”

Fort’s hostility and alienation were shared by the peers he organized. Fort—and by extension the Blackstone Rangers—were shaped by the racial struggles in the neighborhood and the burden that came with being a part of the second wave of Southern blacks moving to Chicago. Hyde Park High School is actually in the Woodlawn neighborhood, which is just south of the Hyde Park neighborhood, home to the University of Chicago. The Green Line elevated train runs along 63rd Street, the main drag in Woodlawn, which today is lined with thickly weeded lots and boarded-up buildings, the vestiges of urban blight.

Jeff Fort not fitting in at Hyde Park High School or in Woodlawn had as much to do with black folks as it did with whites. His mother, Annie Fort, had traded Aberdeen, Mississippi, for Chicago in 1956. In addition to this move, several other social, fiscal, and racial policies—official and unofficial—created the unique set of circumstances that led Fort to the gang lifestyle.

The Fort family moved to Chicago during the city’s second wave of black migration. After living briefly in an area of the city known as the Black Belt, the family relocated to Woodlawn. The other future Blackstone Ranger leader, Eugene “Bull” Hairston, and his family moved in around the same time. But the Hairstons weren’t from the South; they moved from Columbus, Ohio, to Chicago’s “low end,” and then to Woodlawn. Like many black families in the late 1950s, the Hairston family got pushed out of a historically black area and relocated to East Woodlawn because their community had to make room for the construction of new public housing.

Families such as the Forts and the Hairstons differed from other families who came to Chicago during the first wave of migration. Black migration to Chicago was distinctly divided into two waves. The first wave, often referred to as the Great Migration, occurred during and right after World War I. African Americans from urban communities down South were met by friends or relatives at the train station on 12th Street when they arrived in Chicago. They moved into an area of the city dubbed the Black Belt, a group of neighborhoods bounded by 16th Street on the north, 39th Street on the south, State Street on the east, and LaSalle Street, running along the Rock Island Railroad tracks, on the west. Their economic and political power grew; the neighborhood’s blues and jazz music matured. Black businesses thrived, and black residents voted in this pocket of the South Side. They seamlessly eased into the urban way of life and helped build up the city’s black middle class. The black population of Chicago increased by 148.5 percent between 1910 and 1920.

The second wave was a bit different, less sophisticated. Rural Southern blacks were pushed off the land when technological advances after World War II allowed machines to pick cotton faster than people could. In fact, Annie Fort, Jeff’s mother, had been a cotton picker. These black Southerners had been deprived of educational opportunities, kept from voting, and subjected to the Ku Klux Klan. They moved to Chicago seeking a better, Northern way of life. The Chicago Defender, the city’s nationally read black newspaper, encouraged blacks to come to the Promised Land. Once there, they lived in rickety kitchenettes—tiny, cut-up apartments that stacked families on top of one another. Other families moved into newly constructed public housing high-rises that Mayor Richard J. Daley had built to help contain the black population. Public assistance policies didn’t encourage men to live in public housing, and therefore mothers ended up raising their children solo.

Some second-wave migrants, like Jeff Fort and his family, felt alienated from the first-wave migrants. “These newcomers had no experience or relationships. They were rural and they were poor and they lived in these cramped-up quarters. Their neighbors were more fortunate, and they didn’t have anything to do with them. The young ones began to crowd together; this is the emergence of gangs,” Timuel Black says.

Restrictive racial covenants helped keep Chicago’s neighborhoods white from 1916 until 1948. Covenants included language that prohibited blacks from buying or using properties in white areas. If covenants didn’t work, some whites resorted to violence. Blacks didn’t start moving to Woodlawn in earnest until the mid-twentieth century.

Woodlawn’s first residents in the 1850s were of Dutch descent. Two major events came to define the neighborhood. In 1889, Chicago annexed Woodlawn, and in 1893 the World’s Columbian Exposition brought twenty thousand new residents. Sprawling, green Jackson Park was created; new apartments, hotels, and stores were built amid the economic bonanza. Sixty-Third Street boasted specialty shops. English, German, and Irish immigrants moved to Woodlawn. In 1915, blacks were 2 percent of the population.

Simultaneously, Chicago’s black population grew from fifteen thousand to fifty thousand between 1890 and 1915, and the Black Belt boundaries got pushed farther south, all the way to 47th Street. The University of Chicago, chartered in 1890, purchased real estate beyond its Hyde Park location, and the population expansion of the Black Belt concerned school officials. The university’s strategy slyly supported neighborhood organizations that encouraged racial restrictions by contributing to homeowners’ associations in Hyde Park, Kenwood, and Woodlawn. Some of these organizations even bragged about their acumen in holding the color line. The Woodlawn Property Owners League covered property just west of the university. A flyer distributed by the Hyde Park and Kenwood Property Owners’ Association in 1918 asked, “Shall we sacrifice our property for a third of its value and run like rats from a burning ship, or shall we put up a united front and keep Hyde Park desirable for ourselves?”

In 1937, a Chicago Defender editorial condemned Judge Michael Feinberg of the circuit court for upholding a temporary injunction that forced two men who had bought property in Woodlawn to move out of their homes and back into the Black Belt. The editorial also denounced the University of Chicago as the man behind the curtain. “It is well known in Woodlawn that this university is the motive power behind the Restrictive Covenants. In fact, many of the real estate owners in that area refer to the Restrictive Covenants as ‘the University of Chicago Agreement to get rid of Negroes.’ … It is indeed a queer combination, a Jewish judge and a liberal university dedicating themselves to the purpose of maintaining a black ghetto. This judge should be reminded that he is perhaps only a generation away from a Russian or Polish ghetto.”

One of those black men who had bought property in Woodlawn was Carl Hansberry, father to playwright Lorraine Hansberry. A college-educated real estate broker, he was vindicated in 1940 when the U.S. Supreme Court repealed restrictive covenants in Hansberry v. Lee—but the repeal wasn’t enforced. The Hansberry family’s experience became inspiration for Lorraine’s seminal play A Raisin in the Sun, the story of a black family moving from a tenement to a house in a white community. In 1948, the U.S. Supreme Court ruled racial covenants illegal in Shelley v. Kraemer. Coupled with the population boom after World War II and a citywide shortage of housing, this moved blacks into Woodlawn. The neighborhood had the city’s largest number of apartment conversions as property owners divided buildings into kitchenettes to accommodate the influx. In 1930, Woodlawn had nineteen thousand housing units. By 1960 there were twenty-nine thousand units.

In that year the black population in Woodlawn reached 89 percent. High unemployment, overcrowding, and a decrease in city services marred the neighborhood. Some specialty shops along 63rd turned into taverns.

Jeff Fort’s path didn’t surprise Nimocks. “Especially when they come from fragmented families, school dropouts in many cases are psychologically looking for something predictable and orderly. [Gangs] provided that: rules, regulations, strict discipline, standards by which to conduct yourselves,” Nimocks says.

Woodlawn is divided into east and west. East of Cottage Grove were mostly apartment buildings. Families who owned two-flat buildings and single-family homes lived west of Cottage Grove. Nearby grocery stores sold milk-fed chicken and sugar, flour, and coffee from barrels. A White Castle was located on 63rd and Evans. Doctors, Pullman porters, dentists, musicians, and postal workers lived in West Woodlawn. In 1940, the Little Women Club started for seventh- and eighth-grade girls in the neighborhood. A teacher formed a theater group called the Thimble Theater for children. There were Boy Scouts and church youth groups. There were social clubs for teens called the Aristocrats, the Dainty Duchesses, the Nifty Teens, and the Fellows. Lincoln Memorial, the oldest black church in Woodlawn, opened its doors to the Brotherhood of Sleeping Car Porters, the NAACP, and the Chicago Urban League for meetings.

On Friday nights residents could go to the Tivoli Theater on 63rd and Cottage Grove, where Liza Minnelli’s father worked as the band manager. Emmett Till, the teenager who was brutally murdered in Mississippi for allegedly whistling at a white woman, was a chubby boy with copper-colored eyes from Woodlawn. Sam Greenlee, author of The Spook Who Sat by the Door, grew up in Woodlawn. Other notable residents included the Barrett Sisters, father of gospel music Thomas Dorsey, and at least four Tuskegee Airmen.

One white island remained somewhat intact in Woodlawn amid the demographic shifts—Mount Carmel High School, a popular all-boys Catholic school. The Stones never bothered the students there or wandered onto that turf; after all, they weren’t stupid. They knew if they messed with those white boys, the police would handily crush them. Best friends Richard Kolovitz and Dan Brannigan attended Mt. Carmel. They later joined the Chicago Police Department together. Kolovitz is the same age as Jeff Fort and knew of the teen back in the 1960s when he traveled from the Southwest Side of Chicago to attend Mt. Carmel. Kolovitz and Fort’s fates intertwined through the next few decades; Kolovitz would spend much of his career chasing Fort and the Stones.

Legendary organizer Saul Alinsky, whose legacy influenced a young Barack Obama’s South Side organizing in the 1980s, fought for the poor around the country. Chicago native Alinsky started off in his hometown by forming the Industrial Areas Foundation. In the 1930s he organized the Back of the Yards neighborhood, a South Side stockyards community chronicled in Upton Sinclair’s novel The Jungle. Alinsky wanted to expand his organizing beyond white working-class areas in the late 1950s. With racial covenants now illegal, South Side neighborhoods were in flux. Alinsky settled on Englewood, a neighborhood contiguous to Back of the Yards; the organizing had the potential to be powerful. Blacks had started moving into Englewood, a white ethnic community of Norwegians and Germans. The racism was palpable; even though blacks moved into white neighborhoods, the fire department might decide to not respond to a call. However, the Archdiocese of Chicago provided organizational support to Alinsky, and the cardinal had another neighborhood in mind—Woodlawn. The diocese wanted to keep several struggling parishes in that area afloat. They were suffering from white flight, and diocese support was seen as a way to help stabilize the neighborhood. The cardinal offered $150,000, so Woodlawn it was.

Alinsky hired Nicholas Von Hoffman, a young white organizer. Von Hoffman recalled Woodlawn as “a bleak place. But a lot of great people, but it was a bleak world.” The organizers didn’t want the neighborhood to fall into an irreversible slum. They started the Temporary Woodlawn Organization in 1960; the name changed to The Woodlawn Organization (TWO) once the group decided to stick around longer than originally planned. It became clear that members wielded political capital. Local ministers joined the group. TWO rallied block clubs, churches, and other community organizations. Reverend Arthur Brazier, a black pastor at the Apostolic Church of God, was elected president. At first the battle was waged over paltry local education. Residents weren’t as concerned with integration as they were with equity. They took on the conditions at Carnegie Elementary, a school with malcontent teachers, no toilet paper, and a lack of school materials—children performed a strike one day by skipping school. TWO also built alliances with the Woodlawn Businessmen’s Association and mustered up support from residents to develop a better neighborhood plan than the one the city had. With help from renowned urban planner Jane Jacobs, TWO battled raggedy landlords. TWO used the spirit of organizing to foster neighborhood pride.

Then TWO took on another adversary.

In Rules for Radicals: A Pragmatic Primer for Realistic Radicals, Alinsky’s guide for organizing, he discusses how to turn tactics into deliberate acts of power. One of his rules is “pick the target, freeze it, personalize it, and polarize it.” Under Alinsky’s model, this is a universality that organizers must bear in mind. “In a complex, interrelated urban society, it becomes increasingly difficult to single out who is to blame for any particular evil. There is a constant, and somewhat legitimate, passing of the buck,” Alinksy notes. Finding the enemy can be arduous, he says, because the intricacies of urban life put many interlocking institutions—political, metropolitan, corporate—in charge. Therefore, identifying a singular enemy can be a moving target. But Alinsky says that’s no excuse. “Obviously, there is no point to tactics unless one has a target upon which to center the attacks.”

Woodlawn easily found a target—the University of Chicago. The school unveiled its plan for expansion before the Chicago Land Clearance Commission in July 1960. The university wanted to buy up land in Woodlawn. Residents feared a “Negro removal” redux.

A significant neighborhood of the Black Belt, Bronzeville, had been destroyed by urban renewal, also known as “Negro removal,” in the 1950s due to the city’s eminent domain policy. Even with such a large, growing black population, Mayor Daley had desperately tried to contain black neighborhoods for a long time. The high-rise public housing projects started going up in the 1950s, and the so-called crown jewel, the Robert Taylor Homes, opened in 1962. Named after Obama advisor Valerie Jarrett’s grandfather, the homes were the largest public housing project in the world until the last one came down in 2006. Daley also maintained the color line and exacerbated the city’s segregation problems by putting overcrowded black public schools on double shifts instead of building new schools or integrating the adjacent white schools.

Von Hoffman understood the fear of displacement among Woodlawn residents. “At that point, the only people in America who really understood urban renewal was a certain segment of the black population,” Von Hoffman said. “People like Saul completely understood what it was about.” Brazier said, “Homeowners had already experienced displacement from Lake Meadows, Prairie Shores, and South Commons [apartment complexes built and designed for whites]. Many people in Woodlawn had lived and sold in those areas. None of them believed they received proper money.” That stayed fresh on black folks’ minds; they also remembered the University of Chicago’s ugly support of racist covenants.

The university wanted to expand its south campus by gaining full control of 60th and 61st between Stony Island and Cottage Grove. To help get the word out about these plans, TWO relied on the enormous network of janitors. “People had no telephones and there was no telephone tree. We neede...