In the March 1969 aldermanic elections, the machine was facing an increasingly restless electorate. Daley’s hard line on the
Chicago Freedom Movement and the anti-war demonstrators had restored the machine’s traditional hold on the Bungalow Belt wards
that had begun to drift away in the 1963 election over civil rights. But the machine was now facing defections in two other
areas: the black wards and the liberal lakefront neighborhoods. These weaknesses were evident in the aldermanic elections.
On the South Side, there was a hotly contested battle for 2nd Ward alderman. The 2nd Ward, Bill Dawson’s longtime political
base and home of the State Street Corridor, was one of the machine’s “Automatic Eleven.” But independent former social worker
Fred Hubbard was running a dissident campaign against the machine’s candidate, Dawson administrative assistant Lawrence Woods.
“We’re a sure winner,” Dawson declared. “We always are.” But Dawson, who was seriously ill back in Washington, could do little
for Woods, who turned out to be a lackluster candidate, hampered by a bribery indictment on his record. Hubbard, who campaigned
especially energetically in the ward’s many housing projects, won by better than 2 to 1. Hubbard’s victory was a serious setback
for the machine. With black voters making up a growing percentage of the citywide electorate, Daley could not afford to have
the black wards break away.
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Liberal whites were also growing increasingly disenchanted with the machine. Along the lakefront on the North Side, another
reform-versus-machine face-off had developed in Paddy Bauler’s redistricted old ward. When the incumbent alderman was appointed
judge, a young lawyer named William Singer jumped in to challenge the new machine candidate. Singer was a native of Jake Arvey’s
West Side, and had grown up in the middle-class South Shore neighborhood. He had not come up through a ward organization,
and had an unlikely pedigree for an alderman. He was a graduate of Brandeis and Columbia Law School, and worked for U.S. District
Court judge Hubert Will and Senator Paul Douglas. Singer had also worked for Robert Kennedy in his Senate race, and again
in his 1968 presidential campaign. After Kennedy’s assassination, he had been recruited to run George McGovern’s Chicago campaign
office.
Singer had the backing of the Independent Precinct Organization, a fledgling anti-machine group. Just so there were no misunderstandings,
Singer appeared before the 44th Ward Democratic Organization to tell them he would run with or without their endorsement.
Not surprisingly, they did not support him. Understanding Daley’s popularity, Singer did not run an anti-Daley campaign, but
instead tried to articulate a new vision for the city, arguing that residents of the ward should have an independent voice
in City Hall. He emphasized issues like good schools, that cut across machine-versus-reform lines. The result was that he
landed in a runoff election with James Gaughan, deputy county controller and a machine stalwart, for the seat. Singer and
Gaughan reflected a new fault line that was emerging in Chicago Democratic politics. Singer relied on a campaign army of students
and reformers, while Gaughan imported precinct workers from across the city. Singer raised money at coffee klatches in high-rise
buildings, and employed such unmachinelike methods as a group of girls called the Singer Singers, who belted out campaign
theme songs on street corners. Revealing a dark side of Chicago machine politics, Gaughan and his followers made blatant anti-Jewish
appeals to working-class Catholic voters in the non-lakefront end of the district. Singer’s campaign was run, one Gaughan
campaign worker said, by “a brigade of porcupines whose snout is their most prominent feature.” Singer printed up “Porcupine
Power” buttons, and had his campaign workers wear them in Jewish parts of the ward. State treasurer Adlai Stevenson III campaigned
for Singer. “A few years ago, I wouldn’t have thought a grubby aldermanic election could be a great occasion for citizen participation,”
Stevenson said. “But you have to use the opportunities at hand.” The turnout on election day was enormous, and Singer eked
out a victory, winning 11,983 of the 23,263 votes cast.
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The machine’s hold on the city remained secure. Even with Hubbard and Singer joining the City Council, Daley still controlled
at least 37 of its 50 seats. But there was no denying the powerful symbolism of both Dawson’s and Bauler’s old seats falling
to reformers. After the election, Daley indignantly denied reports that his machine was in decline — they were, he said, a
“hallucination of some segments of the press.” Daley may not have admitted the machine’s setback publicly, but he did not
ignore it. Shortly after Singer was elected, Seymour Simon, who was now a North Side alderman, asserted that county clerk
Edward Barrett had fired three of his 44th Ward precinct captains from their county jobs because they had campaigned for Singer.
Daley also lashed out at Stevenson for working for Singer, saying outsiders should not get involved in a ward’s politics.
Daley was angry not only at Stevenson, but at the larger political realities the aldermanic elections had revealed. Daley’s
handling of the 1968 Democratic convention may have been popular with his core constituency, but it had hurt him and the machine
in the city’s liberal precincts. And his hard line on civil rights, and pronouncements like “shoot to kill,” played well in
the Bungalow Belt, but they had alienated other parts of the old machine coalition.
Daley had not yet put the Democratic convention behind him. In March, U.S. attorney Thomas Foran, a machine Democrat put in
office by Daley, handed up a series of indictments in connection with the convention week disturbances. In sharp contrast
with the Walker Commission findings, Foran’s indictments were directed solely at the anti-war demonstrators. The defendants,
who would come to be known as the Chicago 8, were a motley assortment. Yippie organizers Abbie Hoffman and Jerry Rubin and
MOBE leaders David Dellinger, Rennie Davis, and Tom Hayden were among those indicted. But so was Black Panther Party minister
Bobby Seale, who had been in Chicago for less than a day during the convention and had said and done little. Lee Weiner and
John Froines were minor protesters, whose connection to the weeks’ disturbances was equally tenuous. Foran’s indictments were
also a legal stretch, the first ever returned under a provision of the Civil Rights Act of 1968 that made it a felony to “travel
in interstate commerce .... with the intent to incite, promote, encourage, participate in and carry on a riot.”
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On April 23, 1969, after fourteen years and three days in office, Daley became the longest-serving mayor in Chicago history,
beating Mayor Kelly’s record. Baskets filled the corridors of his office in City Hall. Daley’s favorite Irish band, the Shannon
Rovers, played Gaelic tunes as he and Sis came out of his private office to greet the throngs of well-wishers. After the band
broke into “Chicago,” Daley delivered a short homily. “I’ve had the blessing of a fine wife and family, and I’ve tried to
do the best I could while I was mayor. None of us is perfect. But as my good mother and dad would say, do the best you can.”
In a moment of emotion, he added: “I hope that wherever they are Lill and Mike are proud of me.” Daley kissed his wife and
had tears in his eyes. Richard, John, William, and Patricia joined him in the receiving line.
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April also marked the one-year anniversary of Martin Luther King’s assassination. On April 3, the day before the anniversary,
unrest broke out in the Chicago schools by noon, and before the day was over black neighborhoods had once again broken out
in rioting, looting, and sniper fire. Daley cracked down quickly, talking tough and calling out the National Guard. This time,
the conflict ended by nightfall. Nor were the anti-war protests entirely over. More than 10,000 demonstrators marched down
State Street on April 5 to call for an end to the Vietnam War. The march included some dramatic street theater. Demonstrators
ran into a truck called the “war machine” and came out the other end with makeup looking like blood and burns; one group of
marchers held an oversized Uncle Sam covered with simulated dead children. The Chicago police along the route were under instructions
to show restraint. The protesters were told by march organizers not to taunt police, and not to carry “defensive equipment,”
such as helmets or gas masks.
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The opposition to the machine that had shown surprising strength in the March 1969 aldermanic elections continued to increase
throughout 1970. Adlai Stevenson III was becoming a central figure in this reform movement. Like his father, the younger Stevenson
had a complex relationship with Daley and the Democratic machine. He had finished first in the statewide at-large election
of 177 state legislators in 1964, and two years later bucked the Republican tide and was elected state treasurer with Daley’s
backing. In 1968, when Governor Kerner was made a federal judge, Stevenson had made a blunt pitch to machine slate-makers
for the party’s gubernatorial nomination. But Daley had preferred Lieutenant Governor Sam Shapiro, who had worked closely
with him on state legislation. Stevenson then expressed interest in challenging Senator Everett Dirksen in 1968, but Daley
slated state attorney general William Clark instead. After these rejections, Stevenson began to speak out publicly against
Daley, criticizing his handling of protesters during the Democratic convention and later accusing him of maintaining a “feudal”
political system of “patronage and fear.” An informal group called the Committee on Illinois Government — which included Stevenson,
Singer, and Abner Mikva — had begun meeting in Stevenson’s Near North Side home. The committee planned an enormous picnic
in September 1969, in Libertyville, Illinois, at the Stevenson farm. Organizers invited 15,000 reform-minded people and planned
to offer up a manifesto called the Libertyville Proclamation for signatures. A key proviso of the proclamation was that the
Democratic Party should “end reliance upon the purchased loyalties of patronage.”
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Daley decided at the last minute to surprise the reformers by showing up at Libertyville. He arrived in a limousine with Congressman
Dan Rostenkowski, Cook County Circuit Court clerk Matt Danaher, and state auditor Michael Howlett. Wearing his usual formal
attire of a dark suit and tie, Daley stood out from the 8,000 progressives dressed for a country picnic. He took the stage
and delivered a speech aimed shrewdly at his anti-machine audience. Daley spoke of his hard work for Stevenson’s father, for
Senator Paul Douglas, and for President Kennedy. And he called the Reverend Jesse Jackson and Adlai Stevenson III some of
“the great leaders of our day.” Before he was finished, Daley almost sounded as if he himself was joining the anti-machine
ranks. “[W]e need the participation of people who are dedicated to decency in the government,” he said. “And we cannot live
in the past. I welcome the modernization of the Democratic Party.” Stevenson threw away a prepared speech and spoke graciously
of Daley.
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During his own speech, Senator George McGovern stopped to announce the news that Senator Everett Dirksen had died. McGovern
launched into an impromptu eulogy, and Jesse Jackson led a choir in a rendition of “The Battle Hymn of the Republic” as everyone
held hands. But it was Daley who attracted the attention of the seasoned politicians in the crowd. As de facto head of the
Democratic Party, Daley would choose the Democrat who would run against the Republican-appointed interim senator who would
fill Dirksen’s seat. The man Daley decided to nominate was the picnic host. It was a brilliant act of co-optation, removing
the leader of the state’s fast-growing movement of independent Democrats. “On Daley’s part, his performance was a master-stroke,”
wrote
Chicago Tribune
political editor George Tagge. “He assured himself of relative freedom from liberal harassment as he sets about his reelection
plans for spring of ’71.” Like his father before him, the reform-minded Stevenson turned out to be entirely willing to enter
into an alliance with Daley and the Chicago machine in order to get elected. “Stevenson said Daley was a feudal boss,” the
joke went, “but he didn’t say he was a bad feudal boss.”
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