As published in the Chicago Daily News and the Chicago Sun-Times:
Comedian Dick Gregory never shied away from making a joke about racism. His brand of comedy in the 1960s involved making people laugh and (hopefully) squirm in their seats. When he wasn’t doing a bit, Gregory — born Oct. 12, 1932 — hit the front lines of the civil rights movement, participating in boycotts, sit-ins and protests all over Chicago and the country.
In June 1965, the activist focused his attention on ending school segregation in the city and getting rid of School Supt. Benjamin Willis as he and other cohorts attempted to organize a school boycott.
Several other boycotts against Willis — the “Freedom Day” boycott in 1963 and another in 1964 — drew massive headlines and attention but failed to force Mayor Richard J. Daley to get rid of the superintendent, who refused to send Black children from overcrowded schools to less crowded ones in white neighborhoods. Instead of building better schools in Black neighborhoods, he installed portable school rooms pejoratively known as “Willis Wagons” and put many of those schools on double shifts.
During the summer of 1965, Gregory and other activists planned another school boycott that would keep kids out of classrooms, but a temporary court order stalled this effort. On June 9, Chicago Daily News reporter Edmund J. Rooney caught up with the comedian just as he was coming out of jail on a disorderly conduct charge. Despite what other activist leaders thought, Gregory still supported the boycott.
“We’ve had school boycotts in New York with very few students participating, and they helped us get rid of the school superintendent there,” he told Rooney. “Any protest is effective, believe me, even if 100 kids or less stay out of school.”
Gregory vowed to keep up the protests and picketing in the Loop, aiming to hurt the city’s tourism industry, until Willis was removed, Rooney wrote. He refused to accept his constitutional rights “on an installment plan” and insisted that he didn’t care if his activism cost him his career. The comedian also poked fun at Daley, saying he would prefer Alabama Gov. George Wallace to Daley as mayor because “at least Wallace is honest.”
The next day, Gregory joined more than 400 other people to march from Soldier Field to City Hall where an 11-member delegation — including Gregory — attempted to meet with Daley in his office.
“The delegation was told by Jack Reilly, the mayor’s special events director, that Daley was at a groundbreaking, but had agreed to meet with the group at 9 a.m. Monday,” Chicago Sun-Times reporter Ronald Berquist wrote in the June 11 edition of the paper. Berquist didn’t name Gregory as part of the delegation, but photographs taken that day show him outside the mayor’s office surrounded by reporters holding microphones near him.
Outside, marchers sat in the middle of LaSalle Street, the reporter said, but Chicago police did not arrest anyone. The procession downtown had been “orderly,” but it did stall traffic. As they walked, they chanted, “Toss Willis out” and “Willis and Daley, take a vacation from segregation.”
When he finished up inside, Gregory came out of City Hall and spoke to the marchers. “People asked why we marched downtown,” he told them. “As long as Willis stays in, he bugs a whole lot of people.
“But we’ll break even. When we march down here, we bug a lot of people.”