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Does Lori Lightfoot have a path to victory in crowded race for mayor?

Lori Lightfoot, President of the Chicago Police Board

Lori Lightfoot, President of the Chicago Police Board and chair of the Chicago Police Accountability Task Force, is shown in January 2017 discussing the findings of the Department of Justice investigation into the Chicago Police Department. | Sun-Times file photo

There’s no way Lori Lightfoot would have removed herself from the Police Board deciding the fate of Chicago Police Officer Robert Rialmo if she wasn’t running for mayor.

Why else would she have hired a fundraiser, a pollster, a campaign consultant and a firm to handle her direct mail?

If she takes the plunge, Lightfoot will become the eighth candidate to challenge Mayor Rahm Emanuel. Lightfoot, 55, would be one of six black candidates and the second woman. She is the only candidate who is openly gay.

Democratic strategists with no horses in the 2019 race say Lightfoot has the potential to emerge as Emanuel’s strongest challenger — and force the mayor into a runoff — provided she can raise enough money to communicate a story of political independence that remains unknown to many Chicagoans.


“She’s got a long track record on police reform. She’s not viewed as being part of the establishment. She has positioned herself to be a change-agent,” said Victor Reyes, the former Daley political operative who ran the now-defunct Hispanic Democratic Organization at the center of the city hiring scandal.

Victor Reyes (pictured in 2003), said, “Of all the candidates I’ve seen, she probably has the best potential to get Latino votes. | Sun-Times file photo

“Out of all of the candidates I’ve seen, she probably has the best potential to get Latino votes. She is progressive. The Latino vote has become way more progressive since Chuy [Garcia] ran for mayor,” Reyes said.

Lightfoot could probably make it into a runoff in a fractured field with just 30 to 35 percent of the black vote, 25 to 30 percent of the white vote and 35 to 40 percent among Hispanics.

Those numbers are achievable, even if all six black candidates remain in the race, Reyes said.

“It would definitely help to [narrow the field], but having them take votes helps her, too. As long as they’re subtracting from Rahm, they’re helping her,” Reyes said.

Greg Goldner, who managed Emanuel’s 2002 congressional campaign, advised Lightfoot to follow the playbook that carried County Board President Toni Preckwinkle to a landslide victory during a 2010 campaign master-minded by Ken Snyder, who just happens to be Lightfoot’s political consultant.

“She unified the African-American community to a large extent, and she was able to get white progressives,” Goldner said of Preckwinkle.

Former Ald. Dick Simpson (44th) says Lightfoot “could assemble a progressive coalition similar to Harold Washington’s.”

Former Ald. Dick Simpson (44th) is a professor of political science at the University of Illinois at Chicago who backed Garcia over Emanuel in 2015.

Simpson believes Lightfoot has the potential to “assemble a progressive coalition similar to Harold Washington’s.”

“The police issue is the hottest and most important issue of all. … She has a very strong record on the police issue. That will have a lot of appeal in the African-American community,” Simpson said.

Simpson noted that most of the African-American aldermen are “pretty tied” to Emanuel, and “It’s gonna take a lot to break them lose.”

But he advised Lightfoot to turn up the heat and make it uncomfortable for aldermen to stick with Emanuel, no matter how much money he offers to drop into their campaign coffers.

“She needs them to choose sides and she needs to get somebody to choose her …Some group needs to mobilize behind her and really push her candidacy. The ideal would be to get a number of the minor candidates to drop out and endorse her,” Simpson said.

“It all comes down to petition signatures and money raised,” he said. “If she can show the other candidates they have no chance, and that if they rally behind her, the African-American community could gain much more police power and much more results in terms of police reform, that would do it.”

Jacky Grimshaw, who served as a top aide to former Mayor Harold Washington, has her doubts about Lightfoot’s ability to pull it off.

“Dorothy Brown has the church ladies. I don’t know what constituency Lori has,” Grimshaw said. “If police and police misbehavior is your issue, then you pay attention to it. If it’s not, what else have you done? How’s that gonna help me get a job? How’s that gonna help me keep my health care?”

Grimshaw also touched on a sensitive subject: Lightfoot is openly gay.

“Obviously, our society is much more open and accepting. But what should be her niche constituency, some black church folks, are gonna be turned off by that,” Grimshaw said.

Ald. Howard Brookins (21st)

Ald. Howard Brookins (21st) said Lightfoot has virtually no path to victory unless she can convince other African-American candidates, some better known than she is, to drop out and unite behind her. | Sun-Times file photo

Ald. Howard Brookins (21st), former chairman of the City Council’s Black Caucus, argued that Lightfoot has virtually no path to victory unless she can convince other African-American candidates, some better known than she is, to drop out and unite behind her.

“I can’t say that she has a natural constituency. She’s gonna have to work hard for it,” Brookins said. “Paul Vallas is a known commodity in the African-American community. Dorothy Brown, [Troy] LaRaviere, Lori Lightfoot and Vallas are all playing in the same sand box.”

Brookins acknowledged that there is residual anger among black voters about Emanuel’s handling of the Laquan McDonald shooting video. But he doesn’t count the mayor out.

“He’s working hard. He’s been cutting a lot of ribbons. There’s a lot of investment in the African-American community. He’s probably somewhere around 40 percent” of the black vote, Brookins said, holding open the possibility that he might endorse the mayor after assessing the final field.

“I don’t discount the loudest voices. But there are people who still like the mayor and will be with the mayor.

WVON-AM Radio talk show host Cliff Kelley, a former alderman, couldn’t disagree more.

“It wouldn’t surprise me if Rahm didn’t make the runoff,” Kelley said.

“The most expensive piece of political mailing I’ve ever received was a four-page color thing from the White House [in 2015]. The last page said, `To assure that the Obama Museum will be in Chicago, re-elect Rahm Emanuel.’ “If Obama came out and supported him again, nobody would really give a damn. Obama does not have the juice that he had before.”

Lightfoot has a compelling personal story that could be helpful when it comes to introducing herself to voters.

She is the granddaughter of a sharecropper and the daughter of a housekeeper who grew up in Massillon, Ohio.

Before she was born, her father, a factory worker and a janitor, went deaf and spent a year in a coma.

The first black class president of her high school, Lightfoot worked seven jobs to put herself through the University of Michigan, including serving as a cook for the Wolverines’ football training table.

While attending law school at the University of Chicago, she organized campus protests against the discriminatory hiring practices of Baker McKenzie, the multinational law firm. Although Baker McKenzie was one of the university’s biggest benefactors, the protests culminated in the firm being banned from recruiting on the U. of C. campus.

After graduation, Lightfoot joined the U.S. Attorney’s office. She would ultimately become a finalist for the U.S. Attorney’s job that went to Zach Fardon.

On March 6, 2001, Assistant U.S. Attorney Lori Lightfoot talks about the case against Thomas Veysey, who was found guilty of an insurance plot and murder scam by a jury at the Dirksen Federal Building, 230 S. Dearborn. | Richard A. Chapman/Sun-Times

Under former Mayor Richard M. Daley, she served as chief administrator of the Office of Professional Standards, now known as the Civilian Office of Police Accountability.

In 2005, then-Mayor Richard M. Daley asked the team of Lightfoot and Mary Dempsey to clean up a minority contracting program disgraced by scandal.

In the course of cleaning house, Lightfoot and Dempsey made waves by taking on powerful targets. They included Tony Rezko, the now-convicted former chief fundraiser for now-convicted ex-Gov. Rod Blagojevich; Elzie Higginbottom, Daley’s chief fundraiser in the black community; construction giant F.H. Paschen, and the O’Hare outpost of O’Brien’s restaurant, an Old Town institution.

Daley didn’t want them to go that far. He simply wanted them to make the negative headlines tied to the Hired Truck and minority contracting scandals go away.

Kelley said whenever Lightfoot is on his afternoon radio show, “She gets all kinds of accolades and calls and people saying how great she is for standing up to Emanuel.”

The only problem is, “A lot of folks don’t follow this as much as they should.”

“She is not as well-known as some. She has a great chance if she puts together a good campaign team and can raise enough money to get her message out,” he said.

Reyes added, “The only question is, can she put together enough money to communicate her story? She may have a great story but without the resources, even a good story is a tree falling in the forest.”