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For African Americans who traveled to Chicago during and immediately after World War I, fleeing the dangers and humiliations of Jim Crow in the South and lured by the promise of economic opportunity in the North, the community south of downtown variously called the South Side, the Black Belt, and Bronzeville served as the primary point of entry. A handful of much smaller residential settlements also developed immediately west and north of the Loop, but the vast majority of black newcomers headed straight for the South Side. Most of the wayfarers detrained at the Illinois Central Railroad terminal and promptly made their way to the city's predominant area of black settlement. During those years, the homogeneity of Chicago's neighborhoods remained largely undisturbed. Whites maintained a sturdy residential segregation through the use of residential covenants, the enforcement of which remained legal until the Shelley v. Kraemer U.S. Supreme Court decision in 1948. Thereafter, collusion among real estate agents and (if necessary) violence kept the burgeoning African American population bottled up south of the Loop between railroad yards on the west and Cottage Grove Avenue on the east, extending as far south as the Woodlawn and Englewood neighborhoods south of Thirty-Ninth Street. Bronzeville expanded incrementally as time passed to accommodate the growing number of African Americans arriving in a steady stream from Mississippi, Alabama, Louisiana, Tennessee, Arkansas, and other southern states. For the most part, however, the Black Belt remained a narrow, densely populated tract of land seldom more than a few blocks wide that bulged at the seams and spilled over into adjacent white neighborhoods only after fierce resistance. For decades, implacable white hostility kept the South Side's boundaries intact even as the black population increased inexorably.
Despite overcrowding caused by the desperate housing shortage, African Americans residing in the Black Metropolis created a vibrant community in which a professional elite and the members of a commercial middle class lived alongside janitors, domestic workers, manual laborers, porters, and other blue-collar workers of modest means. Dozens of churches, running the gamut from ten-thousand-member Olivet Baptist Church to tiny storefront chapels, represented Pentecostal sects as well as mainstream denominations. The existence of small businesses (both licit and illicit), newspapers, schools, hospitals, jazz nightspots, professional baseball teams, and women's clubs testified to the richness of the cultural life available to the inhabitants of the confined area. South Side residents took great pride in Du Sable High School, Provident Hospital, the Chicago Defender, the Regal Theater, the Illinois National Guard Armory, and other venerable institutions. Social service organizations such as the Phyllis Wheatley Home, Frederick Douglass Center, the Young Men's Christian Association (YMCA), and the Young Women's Christian Association aided uprooted southerners who attempted to find lodging and employment. Organizations dedicated to racial uplift, including branch offices of the National Urban League and the National Association for the Advancement of Colored People, played prominent roles combating discrimination in the workplace and the exclusionary practices of trade unions. Severely constrained by segregation and regularly reminded of their second-class status, black Chicagoans launched enterprises that served South Side customers and founded variegated institutions to construct a wholesome environment. Battling racial inequality and pursuing economic opportunity, they endeavored to fashion a more just society.
Following the lead of other oppressed minorities, African Americans sought to improve their condition by pursuing the benefits offered by politics. Blacks received a modicum of jobs, recognition, and social welfare disbursements in return for votes, but their fealty to the Republican Party ("the party of Lincoln") yielded few rewards in the years after emancipation. The local Republican organization nominated a handful of black candidates for minor offices and appointed a few token blacks to lesser city and county posts, all the while reserving important positions in city government for white politicians. In the first two decades of the twentieth century, as Chicago's African American population grew rapidly in the Second and Third Wards, an emerging cadre of professional politicians on the South Side worked tirelessly to expand black electoral influence. As Oscar De Priest, Ed Wright, Robert R. Jackson, and other black politicos foresaw, a unified African American vote could tip the balance of power between the two political parties or between the Republican Party's warring factions. De Priest became the city's first black alderman in 1915 and won election to the U.S. House of Representatives in 1929, but advancement came grudgingly overall for black office seekers. African Americans still exerted little influence within Chicago's Republican Party, and their compensation for unquestioning loyalty remained minimal.
Like thousands of other African Americans who settled in the bustling African American community developing on the South Side, Harold Washington's parents traveled to Chicago during the First World War. Roy Washington came from a small town in Kentucky in 1918 and quickly found employment in the flourishing meatpacking industry. The son of a Methodist minister, he attended Garrett Theological Seminary and became an itinerant African Methodist Episcopal minister who preached at a number of churches in the city's Black Belt. While working long hours in the stockyards, he attended night classes at the Chicago Kent College of Law. Two years after graduating from law school, he quit his job in Packingtown's slaughterhouses and opened his own legal practice on the South Side. Bertha Jones journeyed to Chicago from the family farm near Centralia in southern Illinois, supported herself as a domestic worker, married Roy Washington, and quickly gave birth to four children. Harold, the third oldest, was born in Cook County Hospital on April 15, 1922. After the birth of the fourth child, when Harold was still a toddler, Bertha filed for divorce and remarried, leaving Roy with custody of their four children. Roy Washington also remarried but remained good friends with his first wife, who subsequently gave birth to six children with her second husband. Bertha lived nearby and never lost contact with her first family, but Roy Washington raised the four children substantially on his own and remained the dominant influence in their lives. Harold Washington, who idolized his father, later said: "I was very fortunate. My father was my role model. He was a real man, he was a good man. For many years he was not only my father, he was my mother. And so I knew who Santa Claus was. He came home every night, put his feet under the table and had dinner with me."
In addition to preaching on Sundays, Roy Washington practiced law and invested extensively in South Side real estate. He became active in the Democratic Party during the 1920s, a time when the overwhelming majority of African Americans still voted for Republican candidates. "Even my mother wouldn't vote Democratic," remembered Harold Washington. As a successful precinct captain in the Democratic Party's Third Ward organization, Roy Washington parlayed his political connections into a job in the city's corporation counsel office as an assistant prosecutor. A conscientious precinct captain who attended promptly to the concerns of his constituents, he became known on the South Side as "Mr. Forty-Eighth Street." Young Harold learned about politics at an early age, soaking up knowledge and observing legendary black politicos in operation. By the time he was sixteen years old, Harold was canvassing the precinct and working at the polls by his father's side. Commenting on the importance of politics to his early home life, he recalled, "My father discussed politics at the dinner table almost every night. ... William L. Dawson, Oscar De Priest, Mike Sneed, Arthur W. Mitchell, and C. C. Wimbish were frequent visitors in our home. ... The only subject that superseded politics in our home was religion."
A group of African American businessmen and professionals, known as the "new breed" because of their desire to wrest power from the hands of unsavory Old Guard black politicians, condemned the bribery, graft, kickbacks, and favoritism they saw all around them on the South Side. They railed incessantly about the open tolerance of vice by corrupt politicians and crooked policemen on the take. In 1947 members of the indignant black elite approached Roy Washington, who was widely respected for his unflinching integrity, about running for Third Ward alderman. Democratic Third Ward committeeman Edward "Mike" Sneed, a crude, uneducated former janitor rumored to be involved with the South Side gambling cartel, ostensibly went along with Washington's candidacy but secretly worked on behalf of the Republican candidate, Archibald Carey Jr. Largely due to Sneed's treachery, Washington lost narrowly in a runoff election to Carey. Later that year, the Chicago Defender's endorsement of Washington notwithstanding, the Democratic Party's leadership chose Illinois state senator Christopher Wimbish to replace the floundering Sneed as Third Ward committeeman. Despite these setbacks, Roy Washington remained unswervingly loyal to the Democratic organization. Regardless of the cutthroat politics practiced in the upper echelons of the political machine, Third Ward residents continued to admire Washington as the benevolent face of the Democratic Party and a trusted ombudsman on Third Ward blocks.
Roy Washington sent Harold and his younger brother, Edward, to St. Benedict the Moor Grammar School in Milwaukee, a Roman Catholic boarding school for black middle-class children, until their repeated acts of rebellion necessitated a change in plans. Revolting against the school's strict regimen and harsh discipline, the boys immediately ran away and hitchhiked home. When the audacious siblings had engineered the hundred-mile escape fourteen times, according to Harold's recollection, Roy capitulated and enrolled the brothers in Chicago's Forrestville Elementary School. Harold attended an overcrowded DuSable High School that had been designed for twenty-five hundred students but, bowing to the city's unyielding segregation policy, somehow made room for more than thirty-five hundred. A tough and determined high school athlete, he boxed as a middleweight and placed first in the 110-yard high hurdles and second in the 220-yard low hurdles at a citywide track meet. He read voraciously, sitting alone in the school cafeteria at lunchtime or secluded in the public library a few blocks from his home in the evenings. Friends recalled that he even read in the dugout in between at bats during baseball games. An intense and curious young man with far-ranging interests, he learned quickly but soon found little intellectual stimulation in his classes. Bored by a curriculum that he said offered no challenges, Harold left DuSable after his junior year and worked for six months at Civilian Conservation Corps camps in Illinois and Michigan before landing a full-time job at a Chicago meatpacking plant. He escaped the drudgery and dangers of the killing floors when Roy Washington used his political connections to land Harold a desk job in the local branch office of the U.S. Treasury. While working at the Treasury, the nineteen-year-old Washington married his childhood sweetheart, seventeen-year-old Dorothy "Nancy" Finch; they divorced, childless, in 1950, and Harold never remarried.
Following the Japanese attack on Pearl Harbor, Harold Washington was drafted into the U.S. Army. Looking back at the Second World War, he spoke disparagingly about his three years in the armed forces. Beginning in boot camp, the site of several violent outbreaks between white and black soldiers, he balked at the regimentation and authoritarianism of military life. Jim Crow conditions in communities near several of the bases in the United States where he was stationed made the experience even more insufferable. Sent to the Pacific theater as a technician in the Army Air Force Engineers, he gathered and tested soil samples on a number of islands as the first step in the construction of landing strips for U.S. bombers. Eagerly taking the opportunity to enroll in the military's continuing education program, he completed thirty correspondence courses offered to overseas personnel. Although the army had promoted him to the rank of first sergeant by the time he received an honorable discharge on January 20, 1946, a disillusioned Washington named the high school equivalency diploma he earned as the only worthwhile outcome of his time in the armed forces.
Near the end of the war, Nancy Washington began writing her husband about a new college forming downtown that everyone on the city's South Side was talking about. In 1945 sixty-eight professors from Chicago Central YMCA College walked out to protest the school's use of racial, religious, gender, and nationality quotas for admission and, with funding from trade unions and local philanthropists, founded an independent, coeducational college devoted to social justice and equal opportunity. Dedicated in 1945 and named after the recently deceased U.S. president, Roosevelt College opened as one of the few fully integrated institutions of higher learning in the nation. The college's commitment to diversity seemed all the more remarkable at a time when most of the hotels and restaurants in the surrounding downtown area refused to serve African American patrons. Providing extensive night school offerings and flexible class schedules, the institution catered to first-generation college students, racial minorities, and international students. In keeping with its reputation as a haven for nontraditional and avant-garde students, Roosevelt College became known as home to an extraordinary number of free thinkers, visionaries, and political radicals — "the little red schoolhouse" to its critics. Reclaiming his job at the U.S. Treasury office after returning to Chicago, Washington made use of his G.I. Bill benefits to enroll as a full-time student at Roosevelt College.
Washington thrived in Roosevelt College's liberal environment, excelling in the classroom, involving himself extensively in student government organizations, and participating in protest activities led by a variety of student groups. The institution nurtured his independent, free-thinking inclinations. Prohibited from joining the college's social fraternities, which were bound by their national charters to exclude African Americans, he helped found a chapter of Phi Beta Sigma, a predominantly black collegiate and professional organization. As president of the college's student council, he extended its reach and broadened its portfolio to increase student influence on campus. In a predominantly white student body — with only about twenty blacks in a graduating class of four hundred — he won election as the college's first African American senior class president. His contemporaries remembered Washington as a calm voice of reason in frequently overheated campus politics, a moderate liberal who got along well with radicals but often stopped short of endorsing their nostrums and tactics. Opinionated but tolerant of other people's views, he defended his ideas firmly but accepted defeat graciously when the opposition prevailed. "He was regarded as an astute, honest, intelligent leader," recalled G. Nicholas Paster, the director of student activities. He chaired the college's first fund-raising drive by students and served on a campus committee that participated in a citywide effort to outlaw racially restrictive covenants in Chicago. In 1949, opposing a witch hunt to identify and punish alleged subversives, he led a delegation of students to the state capital to oppose measures outlawing the Communist Party in Illinois and mandating loyalty oaths for public school teachers. At the height of the Red Scare, the legislation passed.
At Roosevelt College, Washington became acquainted with a number of young African Americans who later became influential figures in the South Side black community. His classmates at the school included, among others, novelist Frank London Brown; Bennett Johnson, a successful publisher and leading political independent; Gus Savage, owner of a weekly chain of community newspapers and later a member of the U.S. House of Representatives from the state's Second Congressional District; and Dempsey J. Travis, a mortgage banker, real estate mogul, civil rights activist, and historian. Travis recalled that, in one late-night bull session, Washington and Savage predicted that one day they would both represent Chicago in the U.S. Congress. In college and for many years thereafter, Travis unsuccessfully attempted to convince Washington to join him in a series of potentially lucrative real estate ventures. Washington repeatedly demurred, forsaking the affluence offered by a business career in favor of his first love, politics.