Comedian Dick Gregory confronts Mayor Daley about school segregation in Chicago

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As published in the Chicago Daily News and the Chicago Sun-Times:

Comedian Dick Gregory has never shied away from making a joke about racism. His genre of comedy in the 1960s was about making people laugh and (hopefully) squirming in their seats. When he wasn’t doing a bit, Gregory – born October 12, 1932 – hit the front lines of the civil rights movement, participating in boycotts, sit-ins, and protests across Chicago and the country.

In June 1965, the activist focused his attention on ending school segregation in the city and removing the school superintendent. Benjamin Willis as he and other cohorts attempted to stage a school boycott.

Several other boycotts against Willis – the boycott of “Freedom Day” in 1963 and another in 1964 – grabbed headlines and garnered attention, but did not force Mayor Richard J. Daley to get rid of Superintendent. , who refused to send black children from overcrowded to less frequented schools to white neighborhoods. Instead of building better schools in black neighborhoods, he installed portable schoolrooms pejoratively called “Willis Wagons” and put many of those schools on double shifts.

In the summer of 1965, Gregory and other activists planned another school boycott that would prevent children from entering classrooms, but a temporary court order blocked that effort. On June 9, Chicago Daily News reporter Edmund J. Rooney met the comedian as he was released from prison for misconduct. Despite what other militant leaders thought, Gregory still supported the boycott.

“We had school boycotts in New York with very few participating students, and they helped us get rid of the principal of the school there,” he told Rooney. “Any demonstration works, believe me, even if 100 kids or less don’t go to school. “

Gregory has vowed to continue the protests and picketing in the loop, in an attempt to hurt the town’s tourism industry, until Willis is sacked, Rooney wrote. He refused to accept his constitutional rights “on an installment plan” and insisted he didn’t care if his activism was costing him his career. The comedian also mocked Daley, saying he would prefer Alabama Governor George Wallace to Daley as mayor because “at least Wallace is being honest.”

The next day, Gregory joined more than 400 other people in walking from Soldier Field to Town Hall, where an 11-member delegation – including Gregory – attempted to meet Daley in his office.

“The delegation was informed by Jack Reilly, the mayor’s director of special events, that Daley was leading the way, but had agreed to meet with the group at 9 a.m. on Monday,” the reporter wrote. Chicago Sun-Times Ronald Berquist in the June 11 edition of the paper. Berquist did not 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, protesters sat in the middle of LaSalle Street, the reporter said, but Chicago police did not arrest anyone. The procession in the city center had been “ordered”, but it blocked traffic. As they walked they chanted “Toss Willis out” and “Willis and Daley take vacation after segregation”.

When he finished inside, Gregory walked out of town hall and spoke to the walkers. “People asked why we were walking downtown,” he told them. “As long as Willis stays inside, he annoys a lot of people.

“But we’re going to break even. When we go down here we disturb a lot of people.


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