Chester K. Gillespie, who moved from Cincinnati to Cleveland as a young boy with his family, often said, "I do not take cases I don't believe in." Gillespie, an African American attorney who would be subjected to numerous incidents of racial discrimination over the course of his career in Cleveland, found no lack of worthy cases to pursue.
Gillespie earned his law degree from the Cleveland School of Law, now part of Cleveland State University. He started practicing law in 1920 and shortly after was appointed assistant city law director. Gillespie worked on multiple cases in regards to equality. In addition to his longstanding involvement in the Republican Party of Ohio, he was president of the Cleveland Branch of the National Association for the Advancement of Colored People (NAACP) in 1936-37. During his term, Gillespie addressed numerous court cases involving racial discrimination in the Cleveland area.
Gillespie battled racism not only in the courtroom, but also in his personal life. As a civil rights attorney, he needed a stable office suite to provide a working environment. In 1937, Gillespie was subjected to a very difficult dilemma. Gillespie worked with another attorney named Clayborne George. Gillespie's law firm occupied offices in the Erie Building at East 9th Street and Prospect Avenue from 1922 to 1937. After facing racial discrimination from numerous downtown building owners when they sought new quarters in 1937, the two gentlemen, with help from the State Commerce Department, moved into a suite at 241 Euclid Avenue.
By 1940 the Telenews modified the building at 241 Euclid, originally constructed as the First National Bank, into a newsreel theater, forcing Gillespie and George to move their law firm to the Hickox Building on the northwest corner of Euclid and East 9th. Gillespie and George remained there until the impending demolition of the building for a new Bond Clothing store again uprooted them in 1945. Their next targeted office space was the Citizens Building across Euclid Avenue. Unfortunately, Gillespie would never move the firm to that location because of racial discrimination. The manager refused in fear he would lose white tenants.
Unwilling to back down, the attorneys threatened to "pitch a trailer downtown" and practice law on the sidewalk if unable to find a proper office. As Gillespie remarked, "It is unthinkable that we will be unable to find a suitable office space in Cleveland which is rated as being the first city in the United States in civil liberties." After failing to force the Citizens Building owner's hand in court, Gillespie moved his law firm into the Kresge building at East 4th and Euclid-the one building willing to add, in the words of the Call and Post, "a touch of color."
After more than a decade of repeated brushes with "Jim Crow" in downtown Cleveland, in 1950, Gillespie and George were welcomed into the Public Square Building at 33 Public Square, which was owned by Columbus real estate magnate John Galbreath. Gillespie felt victorious in finding a suitable office suite after facing many years of tribulations regarding racism and demolition. Despite the fact that the Cleveland City Council had spoken out against racial discrimination against black professionals in the late 1930s, several years after World War II securing nondiscriminatory office leases often still relied on the goodwill of national firms or outside property owners.
Gillespie's struggle mirrored other struggles between the 1940s and early 1960s. African Americans were subjected to unfair working conditions within the city of Cleveland. For instance, Cleveland bank tellers consisted primarily of whites while African Americans held "hidden jobs." blacks were also not allowed to read residential water, electric, or gas meters due to irrational racist fears. Within Cleveland, occupations for blacks were limited to behind-the-scenes jobs. Prior to the 1960s African Americans were hindered from working as clerks on the main floor of downtown department stores. As in banks, they were forced into jobs that kept them hidden away from the public eye.
With the resolution of World War II happening concurrently with Gillespie's search, it may be suggested some realized how detrimental inequality was. After the war, Americans gradually realized they had fought against inequality and oppression in Nazi Germany while discounting their own nation's issues. Persistent unfair treatment happening at home ultimately sparked a breakthrough. As in the South, in northern cities African Americans would be aided by white supporters in the fight to bring equality within the city of Cleveland.