Chapter 2
I N T H E S O U T H S I D E precincts where he’d received a near-unanimous share of the vote in the last mayoral election, Harold Washington was simply “Harold,” a beloved character whose official portrait grinned from the walls of beauty shops and four A.M. taverns, occupying the same position of reverence as St. Anthony of Padua in the homes of Italian Catholics. The black community was his family, because he had no family of his own. Long divorced, childless, he lived alone in a Hyde Park high-rise, his one-bedroom apartment barren except for piles of books and newspapers. He was not so much ascetic as indifferent to anything except politics. His ties were stained. His home-cooked meals were cans of Campbell’s soup boiled in the can, because that didn’t dirty a pot. As a young man, he had been a track star at DuSable High School, but as mayor, he ate so many deep-dish pizzas and Wendy’s cheeseburgers that he snorted, “I can’t run around a dime.” A friend bought Washington an exercise bike, but it sat unpedaled in his living room. The mayor’s idea of recreation was to leave city hall early on Thursday so he could spend the afternoon on political work.
Washington had begun his political career during the reign of Richard J. Daley, when most Chicagoans would have found a black mayor as horrifying as a black next-door neighbor or a black son-in-law. (A lot of them still felt that way even after he won. On the morning after Washington’s victory in the Democratic primary, Chicago Sun-Times wiseass Mike Royko began his column, “So I told Uncle Chester—‘don’t worry. Harold Washington doesn’t want to marry your sister.’ ”)
Had it not been for Washington, Barack Obama might never have left New York. Obama wanted to live in a city with a strong African-American community, a community that controlled its own destiny. In the mid-1980s, that was Chicago.
“I originally moved to Chicago in part because of the inspiration of Mayor Washington’s campaign,” Obama would tell the Congressional Black Caucus Foundation in 2008 as he received its Harold Washington Award. “For those of you who recall that era, and recall Chicago at that time, it’s hard to forget the sense of possibility that he sparked in people. I’ll never forget how he reached out to everyone—black, brown, and white—to build a coalition for change.”
Had it not been for Washington, who ruled for four and a half years without setting off a white-flight panic to the suburbs, black politicians would not have gained the confidence to run for the U.S. Senate, and whites wouldn’t have had the confidence to vote for them. Blacks already had a long history of wielding political power in Chicago, but Washington was the linchpin figure who inspired them to expand their influence throughout the state of Illinois, and finally, across the nation.
“Everybody owes something to Harold Washington, because [his election] was something they never thought could happen,” says Lou Ransom, editor of the Chicago Defender, the city’s African-American newspaper. “If Harold can be mayor, what can’t we do? Obama talks about the audacity of hope. That audacity grew into the notion that a black man can be president of the United States.”
The black political culture that lifted Washington to city hall—and Obama to the White House—began developing even before Washington was born, in 1922. It had its roots in the First Great Migration from the South, which occurred during World War I, when blacks were needed in war industries to replace whites who had been drafted or gone home to Europe to fight for their native countries. Between 1916 and 1920, fifty thousand blacks moved to Chicago, riding north on the Illinois Central Railroad’s “Fried Chicken Special,” which traveled from the Mississippi Delta to the terminal at Twelfth and Michigan in fifteen hours, fast enough to get by on one box lunch. Many were lured by the promises of jobs and freedom in the Defender, which was left in train stations all over the South by Pullman porters.
“Have they stopped their Jim Crow cars?” the Defender asked its Southern readers. “Can you buy a Pullman sleeper when you wish? Will they give you a square deal in court yet? We’d like to oblige these unselfish souls and remain slaves in the South, but to their section of the country we have said, as the song goes, ‘I hear you calling me, and have boarded the train singing “Good-bye, Dixie Land.” ’ ”
Mississippi bluesman Skip James sang about this land of promise in “Illinois Blues,” letting his fellow blacks know that life in Chicago was better than chopping wood in a Delta lumber camp:
You know, I been in Texas and I been in Arkansas
I been in Texas and I been in Arkansas
But I never had a good time till I got to Illinois
Timuel Black’s parents came to Chicago in 1919 as part of that migration. Black’s father was educated enough to read, write, and count, and self-confident enough to show up at the polling places on Election Day, always with a pistol in his pocket for protection. These qualities marked him as a troublemaker in Birmingham, Alabama—a “bad ass nigger,” in the words of his son, who would become black Chicago’s most prominent historian. The Black family was met at the Illinois Central station by relatives, who instructed them on how to behave in Chicago: Don’t spit on the sidewalk; wear a suit, not a pair of overalls. If you’re reading the Defender, put it behind a copy of the Tribune, so white folks can’t see what you’re up to.
Illinois was the Land of Lincoln, home of the man who had freed the slaves, so its race laws were extremely liberal for the era. Blacks had been granted the right to vote in 1870, and the first black was elected to the state legislature in 1876, just as post-Reconstruction politicians were stripping Southern blacks of their short-lived franchise. School segregation was illegal, and a civil rights law guaranteed political equality.
There was, however, a price for this freedom. It was distilled into this saying: “In the South, the white man doesn’t care how close you get, as long as you don’t get too high. In the North, he doesn’t care how high you get, as long as you don’t get too close.” Chicago’s blacks were confined to a long, narrow ghetto known as the Black Belt. It was bounded by Twenty-fourth Street on the north, Thirty-ninth Street on the south, the Rock Island Railroad tracks on the east, and Cottage Grove Avenue on the west. As the black population grew during and after World War I, the Black Belt stayed the same size. The whites made sure of that, both through genteel restrictive covenants among real estate agents and thuggish violence by Irish “athletic clubs,” including the Hamburgs, who counted among their members a teenage Dick Daley. Between 1917 and 1921, fifty-eight homes were bombed by whites who resented the new migrants. In the summer of 1919, a lethal race riot broke out after a young black swimmer was stoned to death for drifting too close to a white beach. Fifteen whites and twenty-three blacks were killed, as young Irish toughs dragged blacks from streetcars and black snipers took potshots at hapless white deliverymen. Over a thousand homes were torched.
The riot taught blacks to stay on their side of the color line. By the end of the 1920s, more than three hundred thousand were corralled into the overcrowded, overpriced, rat-infested slum later portrayed in Richard Wright’s Native Son and Gwendolyn Brooks’s A Street in Bronzeville. Its population density and disease rates were four times that of the surrounding white neighborhoods.
It was this segregation, though, that allowed Chicago’s blacks to achieve political power more rapidly than any community in the country. In that era, blacks still belonged to the Party of Lincoln. Their votes were welcomed by Republican mayor William Hale Thompson, who saw them as a bloc to counter the Irish, Italian, and Jewish immigrants who allied with the Democrats. By the late teens, blacks made up a majority in two of the city’s fifty wards. They were fanatically loyal to Thompson, who led Chicago through most of the Roaring Twenties. In the 1919 mayoral election, the Black Belt gave Thompson 80 percent of its vote, as well as an admiring nickname: “the Little Lincoln.” Following the great tradition of Chicago patronage, Thompson rewarded their loyalty with jobs, so many jobs that white Democrats derisively called city hall “Uncle Tom’s Cabin.” Edward H. Wright, boss of the all-black First Ward, became Thompson’s assistant corporation counsel.
The election contributed to the tension that erupted in the race riot. According to Boss, Mike Royko’s biography of the first Mayor Daley, “Besides the threat they posed in housing and job competition, the blacks had antagonized the heavily Democratic white neighborhoods by voting Republican. They were given credit for Republican mayor William Thompson’s slim victory that spring.” During the campaign, Democrats had driven calliopes playing “Bye, Bye Blackbird” through white neighborhoods and passed out a leaflet depicting Thompson as the engineer of a trainload of Negroes. “This train will start for Chicago, April 6, if Thompson is elected,” the leaflet promised.
More importantly, blacks had their own alderman. Oscar DePriest, first elected to the city council in 1915, would become America’s most significant black politician between Reconstruction and World War II. Like many prominent blacks of that era, DePriest was of mixed race—a “quadroon,” three-quarters white. His parents had been so active in Alabama’s Reconstruction politics that they fled to Kansas after the Jim Crow laws were passed, fearing for their lives. DePriest arrived in Chicago in 1889, where he worked as a housepainter, sometimes passing for white to get jobs. Immediately, DePriest showed a talent for ward politics. A friend invited him to a meeting, where two candidates were vying for a precinct captain post. DePriest exploited the deadlock to win his first political office.
“The vote was twenty-twenty for rival candidates, and I saw right away that a deal could be made,” DePriest would recall. “So I went to one of the candidates and said, ‘Now you’re the one who ought to be captain—I’ll give you two additional votes if you make me secretary.’ The man refused. I went to his rival and made the same proposition. He accepted. I was made secretary. I kept at it because it was recreation to me. I always like a good fight; the chance, the suspense, interest me. I never gambled nor played cards so it was fun to me.”
DePriest was one of Chicago’s great rogue politicians. Chicago’s red-light district was in his ward, having migrated south following the Great Fire of 1871. After only two years on the city council, DePriest was indicted for taking money from brothels and gambling houses, and passing it on to the cops as protection. Defended by Clarence Darrow, he was acquitted but ordered not to run again by the Republican Machine.
DePriest kept his hand in politics by starting his own machine, the six-thousand-member People’s Movement, which backed him when his next opportunity arose. He made it back to the city council in 1927, the same year Thompson was returned to city hall with the support of Al Capone. Thompson appointed DePriest committeeman—party chief—of the Third Ward. The following year, DePriest dutifully supported the incumbent white congressman Martin P. Madden against a primary challenge from an up-and-coming black Republican named William Dawson. Madden won but died before the November election. DePriest was in Indiana, taking the baths at a spa with a group of black politicians, when he heard the news. The next morning, he was in Thompson’s office, demanding the nomination.
“You know, Oscar, I am with you,” the mayor said.
One of DePriest’s rival candidates, William H. Harrison, was an assistant attorney general of Illinois. In July, DePriest was indicted again, this time for allowing black racketeers to operate casinos. Harrison, a black independent who stood to gain by knocking DePriest off the ballot, offered to drop the charges if DePriest dropped his candidacy. DePriest told Harrison to “go to hell” and beat his white Democrat opponent by four thousand votes. Illinois’s First Congressional District has had a black representative ever since, the longest run in the nation’s history. The Voting Rights Act was decades away, but in Chicago, blacks were so concentrated on the South Side that whites couldn’t gerrymander them out of a seat.
Washington, D.C., had not seen a black congressman since 1901, when North Carolina’s George White gave a valediction declaring his defeat “the Negro’s temporary farewell to the American Congress.” DePriest wasn’t just the South Side’s representative. He stood for his entire race. In his maiden speech, favoring a bill to investigate American imperialism in Haiti, he scolded Democrats for caring more about West Indians than sharecroppers.
“I am very glad to see the gentlemen on the minority side of the House so very solicitous about the conditions of the black people in Haiti,” DePriest said. “I wish to God they were equally solicitous about the black people in America.”
DePriest appointed blacks to Annapolis and West Point. He fought to fund D.C.’s all-black Howard University. In the Capitol, an Alabama senator tried to prevent DePriest from using the Senate dining room. You’re not big enough to stop a black congressman from sitting where he wants, DePriest told the senator.
In Chicago, pride in the only black congressman ran deep. DePriest was a hero when he walked down Forty-third Street, in the heart of the Black Belt (which had expanded since World War I), visiting speakeasies with his son, Oscar Jr. White Chicago may have had a Second City complex toward New York City, but black Chicago didn’t. New York wouldn’t achieve black representation until 1944, when Adam Clayton Powell Jr. was elected in Harlem. Harlem’s population was more diverse, with blacks from the South Atlantic states, the West Indies, and Africa. It lacked the political unity of Chicago, where entire families and communities had migrated up from Alabama, Arkansas, and Mississippi. New York also lacked factories and the fat paychecks they provided. When South Siders drove to New York to see Joe Louis fight, they paraded their sedans through Harlem to envious whistles.
“The story of how the black migrants from the South gathered their strength to fulfill George White’s prophecy is a story of machine politics—Chicago style,” wrote St. Clair Drake and Horace R. Cayton in Black Metropolis, their study of the Black Belt.
So it took a shady politician from the Windy City to fulfill the promises of the Declaration of Independence and the Fourteenth Amendment. The beauty of a machine is that it offers a little something for everyone, even if it’s only a free turkey for voting on Election Day.
DePriest liked to say, “I am a Negro before I am a Republican,” but that wasn’t enough to save his career when the New Deal converted blacks to the Democratic faith. DePriest had been a Herbert Hoover congressman. In 1934, he was defeated by a Democrat, after a black committeeman reminded his constituents that “Abraham Lincoln is dead.”
The next boss of black Chicago was William Dawson, a ghetto grandee who strutted around Bronzeville on a wooden leg, which he stomped to give emphasis to his threats. Unlike his black power predecessor, Dawson didn’t flaunt his race. If DePriest had been a Negro before he was a Republican, Dawson was a machine hack before he was a Negro.
Like most blacks who came of age before the New Deal, Dawson began his career a Republican. He changed parties only after seeing more opportunity on the other side of the ballot. After six years as alderman of the Second Ward, he lost his bid for reelection, so he accepted Mayor Edward Kelly’s offer to become Democratic committeeman. Soon, he was a congressman, sitting in DePriest’s old seat.
Dawson’s most generous political donors were the policy kings, the South Side numbers runners who sold poor blacks a chance at winning the rent money, at just ten cents a spin. They were a major force in the Black Belt’s economy: The most successful owned vacation homes in Paris and Mexico.
“Now, if I were to run for a political office, I would have to raise campaign expenses,” Dawson explained. “If I went to every professional man in the town, I would not be able to raise two hundred dollars. But if I went to the vice lords and policy kings, I would get two or three thousand from a couple of them.”
At Dawson’s urging, Mayor Kelly protected the policy kings. As Dawson put it, “If anybody is going to make money out of the frailties of my people, it’s going to be my people.”
But after Kelly went, so did the protection. As soon as Kelly was out of power, Chicago’s organized crime mob, known as the Outfit, began knocking off policy wheel operators in a hostile takeover of the numbers game. Dawson appealed to Kelly’s successor, Mayor Martin Kennelly, to defend his most important source of campaign funds. Kennelly, Chicago’s postwar mayor, fancied himself a reformer (which made him completely out of place in city hall), and reformers don’t stand up for gamblers. Dawson didn’t forget the snub. When Kennelly tried to run for a third term in 1955, Dawson helped dump him in favor of Richard J. Daley. The Dawson-controlled black wards gave Daley over 70 percent of the vote.
Dawson was able to amass more power than DePriest because the Black Belt had changed since DePriest’s day. In 1948, the Supreme Court outlawed restrictive housing covenants, and the well-to-do professionals who had provided the Black Belt with intellectual and political leadership immediately left for more prosperous neighborhoods. They were replaced by blacks of the Second Great Migration, many of them sharecroppers dispossessed from the Mississippi Delta by cotton-picking machines. Poor, barely literate, and country to the bone, these newcomers needed the jobs and welfare that only a machine could provide. Dawson could get you a nice apartment at one of the brand-new high-rise housing projects or a gig at the post office, sorting mail from midnight to eight.
Mayor Daley, who refused to allow anyone other than Mayor Daley to make decisions in Chicago, did not allow Dawson to choose his people’s aldermen. Instead, he stocked the city council with a cast of docile South Side and West Side mediocrities known as the “Silent Six,” who could be counted on to vote with the Machine, even when the Machine was blocking an open housing law that would have allowed poorer blacks to escape the ghetto. Dawson resisted Daley’s power play, but as it turned out, the Silent Six helped solve a thorny problem for Daley’s Machine and Dawson’s sub-Machine.
“The blacks wanted out of their ghetto,” wrote Bill and Lori Granger in Lords of the Last Machine: The Story of Politics in Chicago. “But how could the Machine encourage this without breaking up the old ethnic neighborhoods that gave it its strength? Nor did black Machine leaders have any interest in breaking up the tight black ghetto. Under Bill Dawson it was a powerful force as well as economically tied to the Dawson machine. Why let the chickens get out of the coop?”
DePriest, Dawson, and Powell all had one trait common to pioneering black politicians: light skin. Down unto Obama, mixed-race politicians have made advances that were later shared by the entire community. Virginia’s Douglas Wilder, the first black governor since Reconstruction, was also light skinned. It’s as though the color barrier can only be breached by someone whose ancestors have already lived on the other side.
“They were considered white,” Timuel Black says of Chicago’s first black congressmen. “They had to be smarter because they had white ancestors. That’s part of the culture of America. That’s true even today. Nobody speaks about it, but they can see it.”
Black Chicago’s fealty to the Machine began to fall apart during the civil rights movement of the 1960s. The poor black wards, controlled by Dawson, had provided the votes to put Daley in office and keep him there. One West Side ward, which was run by white precinct captains and white mobsters, voted for Daley 20,300 to 800. City hall rewarded its most loyal supporters with slights. Overcrowded black schools held classes in trailers, while white schools across the color line sat half-empty. The Robert Taylor Homes, the city’s largest housing project, was separated by a highway from Daley’s all-white Bridgeport—a highway placed there to maintain the color line. When black students moved onto Daley’s street, he did nothing to stop the demonstration that drove them out.
Those insults could be borne—things were still worse down South—but when Daley’s police began killing blacks, the community revolted. Daley, who had been seen as an antiwar liberal in the mid-1960s, changed his political persona to match the country’s call for law and order. First, he publicly ordered police officers to “shoot to kill” arsonists during the West Side riots following Martin Luther King’s assassination. The next year, police gunned down Mark Clark and Fred Hampton, the leaders of the local Black Panther Party. The men were shot to death in their beds during an early morning raid that the police and newspapers portrayed as a “wild gun battle.” The killings galvanized Chicago’s black political establishment. Ralph Metcalfe, the Olympic track star who had been a member of the Silent Six before succeeding Dawson in Congress, was transformed into a bitter critic of the mayor. Blacks couldn’t take down Daley, but they did go after his hand-picked Cook County state attorney, Edward Hanrahan, who had plotted the Black Panther raid. Hanrahan was thrown out of office in 1972 by a coalition of inner-city blacks and suburban Republicans. It was the Machine’s first big defeat, but a bigger one was coming. In the winter of 1979, Daley’s successor, Michael Bilandic, dealt with the commuting woes created by a blizzard by ordering L trains to speed past stops in inner city neighborhoods. The snowfall was bad timing for Bilandic. The Democratic primary for mayor came around a few weeks later, too soon for the black community to forget the slight. Blacks voted overwhelmingly for Bilandic’s opponent, Jane Byrne.
“Byrne’s unprecedented showing accordingly provided black voters with a new sense of themselves, and the machine lost its aura of invincibility,” wrote William J. Grimshaw in his book Bitter Fruit: Black Politics and the Chicago Machine, 1931–1991. “If black voters could elect a female mayor, why not a black mayor?”
Why not, especially when the female mayor turned out to be no better than the Machine mayor. Byrne dumped blacks from the school board, replacing them with whites. Desperate for a champion, black leaders pleaded with Harold Washington to run for mayor.
Washington had begun his political career as a minor operator in William Dawson’s South Side Machine. In Chicago, every ambitious young politician needed a “Chinaman,” a powerful patron who would secure him a government job and promote him for office when a spot on the ballot opened up. Washington’s Chinaman was Ralph Metcalfe. Washington inherited a precinct captaincy from his father, and Metcalfe quickly put him on the city hall payroll as a lawyer in the corporation counsel’s office. After Washington got into a shouting match with a white colleague, threatening to throw the man out the window, he stopped showing up for work, except on payday. That was okay, because he was still doing the important part of his job: getting out the vote for his Chinaman. In 1964, Metcalfe sent Washington to Springfield as a state representative, where he embarrassed the Machine by sponsoring an anti–police brutality law. He turned out to be a liberal, in tune with the movements of the 1960s and 1970s, campaigning for affordable housing, consumer protection, women’s liberation, and abused children. After Metcalfe died, Washington beat the Machine loyalist chosen to take his old patron’s place. He was congressman for the historic First Congressional District. In Chicago, that was as high as a black politician could go.
At first, Washington refused the calls to run for mayor. He had tried it in 1977, lost badly, and was enjoying his new job as a congressman. Then he offered a condition: He would run if one hundred thousand new black voters registered. Registrars hit the streets, urging blacks to “send Reagan a message” and “get Jane Byrne.” They added 125,000 names to the rolls, expanding the black electorate by 30 percent.
Washington won the 1983 Democratic mayoral primary by defeating a pair of Irish politicians. Mayor Jane Byrne and Cook County state’s attorney Richard M. Daley split the white vote, allowing Washington to squeak through with 36 percent. In a city that hadn’t elected a Republican mayor since Big Bill Thompson, that should have been enough to ensure him victory. But Chicago had never elected a black mayor. The day after the primary, Irish, Poles, and Italians who had been baptized in the Democratic Party began flocking to the Republican nominee, a Jewish attorney named Bernard Epton.
The election was entirely about race. When Washington campaigned at a church on the white northwest side, he was greeted by a jeering mob and the graffito DIE, NIGGER, DIE. On the South Side, a bus driver half-jokingly told his passengers, “Anyone here who’s not going to vote for Harold Washington, get off my bus.” In the black community, to be seen without a blue “Washington for Mayor” button was to be poorly dressed. Unfortunately, Washington’s inattention to his personal and professional affairs had left him with a record of tax problems and attorney-client complaints, which allowed whites to insist their opposition had nothing to do with his blackness. He was so careless he’d neglected to file taxes for several years in the 1960s, which earned him a forty-day jail sentence. Epton ran an ad highlighting Washington’s messy finances, ominously urging Chicagoans to stop him “before it’s too late.”
The city was so polarized that the chairman of the Cook County Democratic Party, Alderman Edward Vrdolyak, secretly urged white precinct captains to work for the Republican. He thought, at least, that he was doing it secretly. Two newspaper reporters had slipped into a meeting where Vrdolyak declared that the contest was “a racial thing.” Their stories ran the weekend before the election. Washington won with 51 percent of the vote—all the blacks, most of the Latinos, and just enough white lakefront liberals who were reluctant to vote for a tax cheat but even more reluctant to support a candidate they thought was appealing to racism.
After Washington took office, Vrdolyak again tried to thwart him by forming “the Twenty-nine,” a bloc of white aldermen who stonewalled every mayoral appointment and initiative. A local comedian dubbed the deadlock “Council Wars.” Time magazine called Chicago “Beirut on the Lake.” The black community was so politicized, so united in its support of Washington, that street-corner idlers discussed his school board appointments as avidly as they did the Bulls’ first-round draft pick, a shooting guard from North Carolina.
Washington’s election gave blacks a new sense of political confidence. To Ebony magazine, published in Chicago, the victory was as much an assertion of black power as Joe Louis’s knockout of Max Schmeling. Chicago’s blacks had knocked down the Irish Machine, which had ruled the city for half a century. Who was next?
The national Democratic Party was next. Jesse Jackson was inspired to run for president during the 1983 mayoral primary, after seeing former vice president Walter Mondale and Senator Edward Kennedy snub Washington. (Mondale endorsed Byrne, while Kennedy backed Daley, a fellow Irishman whose father had helped elect John F. Kennedy.) Jackson started a national voter registration drive and declared that blacks would no longer be taken for granted by the Democratic Party.
“Washington’s win,” he said, “is a particularly important victory, because it signifies to the world that a new inspiration is at work right here in Chicago.”
The publicity-loving Jackson may have been eager to snatch back the title of America’s leading black politician (with Washington as mayor, Jackson was no longer even number one in Chicago). Whatever the motivation, Jackson’s run for president made an impression on Obama, who was still a twenty-two-year-old newsletter editor in New York. To a young black man with an interest in politics, seeing Jesse Jackson on the same stage as Mondale, Gary Hart, and John Glenn was a very big deal.