Rev. Jesse Jackson and Chicago mayors, a tense, fraught relationship

Rev. Jesse Jackson had a complicated, fraught and sometimes contentious relationship with Chicago mayors.

For 60 years, nine mayors had no choice but to contend with him and sometimes defer to him — even though they often didn’t like it.

They couldn’t afford not to defer to him. He was a forceful presence who knew how to organize economic and political boycotts, work the media to generate headlines and exert maximum political pressure to accomplish his civil rights goals.

A native of Greenville, S.C. Jackson moved to Chicago in 1966 to enroll at the Chicago Theological Seminary and joined the Chicago Freedom Movement, the local off-shoot of the civil rights movement led by Rev. Martin Luther King Jr.

Then-Mayor Richard J. Daley was at the zenith of his power. The civil rights movement threatened the enormous power that Daley wielded as the nation’s most powerful big city mayor and chairman of the Cook County Regular Democratic Organization — long before the Shakman decree banned political hiring and firing.

“Jesse’s whole thing was he attacked power, and nobody was a bigger representative of power at that time than the mayor,” Bill Daley, former chief of staff in Barack Obama's White House, said of his father.

“He probably thought [Jackson] was a, quote, `troublemaker,’ because he was pushing all the time for change — and most people in charge of things don’t like change.”

Fortunately for the elder Daley, there were “other ways to reach into the Black community” in those days through business, religious and political leaders, many of whom were, as Bill Daley put it, “very leery of Jackson, this young guy from South Carolina coming and and pushing them around.”

But the elder Daley still had to deal with Jackson.

“Jesse would complain about this or that and my dad would try to figure out, like he did with Martin Luther King, how to compromise, make a deal and not let things get out of hand,” Bill Daley told the Sun-Times.

Jacky Grimshaw, who served as Mayor Harold Washington’s director of intergovernmental affairs, recalled the elder Daley being “mean and disrespectful” when King arrived in Chicago and declared the city “worse than the south.”

“Jesse was pushing civil rights and supporting King on the housing crusade. Richard J. wanted control. He didn’t want to give up an inch of power,” Grimshaw recalled. “His position was, `No. I’m not doing that.’ And then, after the fight died down, he would do it… He might not do what was asked. But he would do something.”

Jackson and Daley clash over the 1972 convention

The biggest confrontation between Richard J. Daley and Jackson took place in 1972.

That’s when Jackson joined forces with then-Ald. Bill Singer (43rd) to unseat the Daley Democrats at the Democratic National Convention in Miami Beach — and replace them with a diverse group of delegates aligned with George McGovern. Daley was so furious about being embarrassed on the national stage, he boycotted the Miami Beach convention.

Singer said Jackson got involved in that fight belatedly, and only after the Singer-chaired Committee on Illinois Government sent a letter to Richard J. Daley informing him of the need to overhaul the Illinois delegation.

“The DNC had told us we had to have a balanced delegation of women, Hispanics and African-Americans and I just thought, what better person to be that than Jesse and, because of his prominence, I asked him to be the co-chairman,” Singer recalled. “He was an effective spokesperson for the rules of the convention… Jesse was given a prime time spot to speak at the convention, and did very effectively.”

When the Blizzard of 1979 buried Chicago and paralyzed the CTA, Daley’s successor, Michael Bilandic, made the politically fatal decision to bypass stations in Black neighborhoods.

Jackson endorsed mayoral challenger Jane Byrne.

“Byrne carried the Black community and Jesse had a major impact,” said veteran political operative Don Rose, who ran Byrne’s campaign.

Bill Daley added, “That was the spark that elected Harold Washington. No doubt about it.”

The political alliance between Byrne and Jackson was short-lived.

Jackson’s relationship with Byrne sours

“She didn’t put him on the transition team and it was war from the very beginning,” Rose recalled. “She was afraid of him. She never engaged in open warfare and denunciations. But she was always hoping that some of her Black toadies would neutralize him, which they did not.”

Determined to stop then State’s Attorney Richard M. Daley from claiming the political throne, Byrne replaced Blacks with whites on boards overseeing the Chicago Public Schools and the Chicago Housing Authority. Jackson retaliated by organizing a boycott of Chicagofest and convinced Kool & the Gang to cancel their performance at the popular festival.

Harold Washington rode the wave of political outrage against Byrne and became Chicago’s first African-American mayor. Although Jackson’s Black empowerment crusade had planted the seeds for Washington’s election, there was a twinge of jealousy to their relationship, Rose and Grimshaw recalled.

“He realized that once Harold Washington was elected, he was no longer No. 1 in town… which is why he went to Washington soon after that," Rose said. “When people realized that politics was power and Jesse’s kind of leadership was inspiration, he put himself out of a job in a way. I’m sure he wished that he had been mayor. But on the other hand, he did work very hard for and was very important in Harold’s election.”

By the time Richard M. Daley began his record-setting 22-year reign, Jackson was already involved in the first of two presidential campaigns.

But that didn’t stop the civil rights icon from returning to his Chicago base on occasion to prod and pressure Richard M. Daley, just as he did with Daley's father.

“He would attack Rich on issues, on stuff he did, and not enough minority contractors," Bill Daley recalled. "He would march around City Hall on stuff, but Rich never took the bait. He never got hot.”

“Over the 22 years, they had an arms-length relationship and probably helped each other at times and, at other times, dumped on each other. But nothing dramatic.”

Collaboration and confrontation

Former Mayor Rahm Emanuel was a student of power who had a healthy respect for Jackson. When Emanuel closed 50 Chicago Public Schools in one fell swoop, Jackson challenged the decision both publicly and privately.

“I told him the truth. I said, `My life would be easier, Rev. Jackson, if I never did this. Those kids lives would not be.' I said parents are taking their kids out of school. They’ve decided these schools are not only shrinking in population, but failing academically. He didn’t agree with it,” Emanuel told the Sun-Times.

Jackson was also among those who led an avalanche of protests against Emanuel after the court-ordered release of the video showing Chicago police officer Jason Van Dyke shooting 17-year-old Laquan McDonald.

In the furor that followed, Emanuel openly acknowledged that there was a code of silence in the Chicago Police Department. Jackson was in the City Council chambers when Emanuel “addressed it head-on.”

“There was collaboration. There was coordination. There was conflict and there was confrontation. All of it. We had a relationship. And he wouldn’t want it any other way,” Emanuel said of his relationship with Jackson.

“There were times when he thought he could rent the mayorship. And I said no. And there were other times, like what we did [with expanded minority set-asides] on the Red Line. He was an essential partner who challenged us to do better and we did.”

During a telephone interview with NBC 5 Chicago, former Mayor Lori Lightfoot recalled being somewhat intimidated by Jackson and dragging herself to a unity breakfast with County Board President Toni Preckwinkle at Operation PUSH, after she and Preckwinkle were summoned there the morning after Lightfoot’s landslide victory.

Mayor Brandon Johnson, a former paid organizer for the Chicago Teachers Union who often talks about having been arrested while protesting Emanuel’s 50 school closings in 2013, said in a statement he was “devastated to lose my mentor and friend,” adding that he was “personally grateful for Rev. Jackson and his family embracing me and our city with his wisdom and guidance.”

Shortly after taking office, Johnson delivered a keynote address at the Rainbow PUSH annual convention and paid tribute to the civil rights icon.

“Throughout history, there have been exceptional individuals who rise above the ordinary [in] the perilous journey from freedom to equality. Rev. Jackson embodies that," Johnson said that day. "I am not here without the extraordinary individual who has forever impacted my life, and the world's life."