Despite efforts to recruit youth and promote involvement, participation in the "Days of Rage" demonstrations was not as broadly based as advertised, or as participants had hoped. About 800 Weatherman members showed up prior to October 8 and faced 2000 police officers. No more than 300 were left willing to face the enormous gathering of police a second time around on the evening of Wednesday, October 8, 1969, in Chicago's Lincoln Park, and perhaps half of them were members of Weatherman collectives from around the country. The crowd milled about for several hours, cold and uncertain. Tom Hayden gave a short speech, telling the protesters not to believe press reports that the Chicago 8 disagreed with their action. Abbie Hoffman and John Froines, other members of the Chicago 8, also came but decided not to speak and quickly left. Late in the evening, Jacobs stood on the pedestal of the bombed Haymarket policemen's statue and declared: "We'll probably lose people today... We don't really have to win here ... just the fact that we are willing to fight the police is a political victory." Jacobs' speech compared the coming protest to the fight against fascism in World War II. By this time there were around 350 protesters. Jeff Jones announced "I am Marion Delgado" an adopted folk hero of Weatherman (Delgado was a five-year-old Chicano boy who had derailed a passenger train in 1947 by putting a slab of concrete on the track) and for the first time told the crowd the target of the march: the Drake Hotel, home of Julius Hoffman, the judge in the Chicago 8 trial.
Finally, at 10:25 p.m., Jones gave the pre-arranged signal over a bullhorn, and the Weatherman action began. John Jacobs, Jeff Jones, David Gilbert and others led a charge south through the city toward the Drake Hotel and the exceptionally affluent Gold Coast neighborhood, smashing windows in automobiles and buildings as they went. The protesters attacked "ordinary cars, a barber shop...and the windows of lower-middle-class homes" as well as police cars and luxury businesses. The mass of the crowd ran about four blocks before encountering police barricades. The mob charged the police breaking off into small groups, and more than 1,000 police counter-attacked. Although many protesters had motorcycle or football helmets on, the police were better trained and armed; nightsticks were aimed at necks, legs and groins. Large amounts of tear gas were used, and at least twice police ran squad cars full speed into crowds. After only a half-hour or so, the riot was over: 28 policemen were injured (none seriously), six Weathermen were shot and an unknown number injured, and 68 protesters were arrested. Jacobs was arrested almost immediately.
October 9, 1969
The next day a "Women's Militia" of around seventy female Weatherman members met at Grant Park, where Bernardine Dohrn addressed them. The plan was to raid a draft board office, but they were overpowered by police when they tried to leave the park. Later that day Illinois Governor Richard Ogilvie announced that he had called in over 2,500 National Guardsmen to "protect Chicago". Weatherman cancelled protests that had been planned for that evening.
Supporters of the Revolutionary Youth Movement II (RYM II), led by Klonsky and Noel Ignatin, held peaceful rallies of several hundred people in front of the federal courthouse, an International Harvester factory, and Cook County Hospital. The largest event of the Days of Rage occurred on Friday, October 10, when RYM II led an interracial march of 2,000 people through a Spanish-speaking part of Chicago. At the October 9 RYM II rally at the federal courthouse Black Panther leader Fred Hampton disassociated his group from Weatherman, saying, "We do not support people who are anarchistic, opportunistic, adventuristic, and Custeristic." That night Weatherman uncovered a police informant, who was then severely beaten by one member of the group. The assailant, who immediately appeared on wanted posters, became the first member of Weatherman to go underground.
October 11, 1969
On Saturday, October 11, Weatherman attempted to regroup and reignite the revolution. About 300 protesters marched swiftly through The Loop, Chicago's main business district, watched over by a double-line of heavily armed police. Led by Jacobs and other Weatherman members, the protesters suddenly broke through the police lines and rampaged through the Loop, smashing windows of cars and stores. But the police were ready, and quickly sealed off the protesters. Within 15 minutes, more than half the crowd had been arrested—one of the first, again, being Jacobs.
Richard Elrod, a city attorney, was paralyzed after he attempted to tackle Weatherman member Brian Flanagan. Elrod accused Flanagan of attacking him, while Flanagan maintained that Elrod simply hit a concrete wall. Flanagan was charged with attempted murder and other crimes but was acquitted on all counts.
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