To win historic runoff, Lightfoot, Preckwinkle must overcome new obstacles

With a five-week sprint to the finish line, Lori Lightfoot and Toni Preckwinkle have very different paths to victory in one of the most historic and unpredictable mayoral elections in Chicago history.

For Lightfoot, the formula is simple: raise money and do it quickly to define yourself to an expanded electorate before your opponent can define you.

Reassure a nervous business community that backed Bill Daley that you have the gravitas to actually run the city, so they’ll open their wallets. Expand your base beyond the North Side and lakefront wards by hammering away at taxes and corruption.

For Preckwinkle, the task is a bit more complicated: Drive up Lightfoot’s negatives. Consolidate a divided labor community. Shape up a campaign apparatus that shot itself in the foot. And “quit hiding” from the news media to remind voters of the authenticity they once found appealing.

“She has to change her approach to this election. She’s got to talk to the media. She’s got to get out and talk to people. She’s got to talk in her ads. People need to see her and hear from her and re-connect with the Toni that they remembered before she became the Toni that she is now,” said one strategist with no ties to any mayoral campaign.

“They ran this sort of frontrunner campaign, this inevitable-that-she’s-gonna-be-mayor campaign and it didn’t work. By the time they were ready to switch strategy, it was too late. She’s got to get back to being her and remind voters why she’s been called a reformer for all these years. It starts with being genuine.”

Most unaffiliated political strategists say the race appears to be Lightfoot’s to lose.

That’s because she has successfully portrayed herself as the change agent in a change election dominated by one of the biggest City Hall corruption scandals this city has ever seen, with longtime Ald. Ed Burke facing charges of attempted extortion.

But Lightfoot’s image could change in a heartbeat — as quickly as Preckwinkle airs her first campaign commercial.

“Preckwinkle comes with very high negatives. To change that, she has to drive up Lori’s negatives. … You get on the air first while Lori doesn’t have any money and you attack her. This is gonna be a race where she has to savage Lori to win,” said a political strategist for one of the dozen other mayoral candidates.

The strategist noted that Preckwinkle out-raised Lightfoot by a 3-to-1 margin and enters Round 2 with $3.9 million compared to Lightfoot’s $730,940.

“Lori’s biggest problem is, she didn’t raise any money. She flew under the radar. Nobody attacked her. And that’s not gonna be the case this time. Lori has got to be able to raise the money to defend herself because Toni and SEIU are gonna come after her with every dollar and every punch they can land,” the strategist said.

On election night, Preckwinkle telegraphed her intention to go negative. She talked about Lightfoot’s dearth of executive experience and the “multiple appointments” Lightfoot accepted under two mayors, Richard M. Daley and Rahm Emanuel, while Preckwinkle had “fought the powers … trying to hold this city back for decades.”

That’s nothing compared to the line of attack Preckwinkle has planned against Lightfoot, according to senior campaign adviser John Hennelly.

“She has conned progressives … [into believing] she’s a progressive. She is not. She’s a corporate attorney who defends Wall Street banks. She was appointed by Rahm and Daley numerous times and defended corrupt and violent police officers. She’s not a progressive.”

Of the two candidates in this race, “the only candidate with a record of bringing change is Toni. … Lori has not brought any change to Chicago. It’s a complete fraud. We feel confident that, once the true story about Lori gets told, progressives will come home for Toni. They remember her record as a progressive.”

Lightfoot co-chaired the Mayor’s Task Force on Police Accountability; that group’s scathing indictment of the Chicago Police Department laid the groundwork for the U.S. Justice Department to do the same after the police shooting of Laquan McDonald.

On Wednesday, Lightfoot told the Chicago Sun-Times she is “very proud of what we were able to accomplish” while leading the Office of Professional Standards under Daley, now known as the Civilian Office of Police Accountability.

“It was a difficult circumstance, particularly being embedded within the Chicago Police Department. But I know we made significant progress on a number of fronts — not the least of which was holding officers accountable when they lied, either by omission or commission,” Lightfoot said.

Lightfoot also made no apologies for the top jobs she held under Daley and Emanuel — at OPS, the Office of Emergency Management and Communications, the Police Board and the Department of Procurement Services after the minority contracting scandal.

“If she wants to attack me for being a public servant and stepping up, particularly at times of need in the city, I’m happy to have that conversation,” Lightfoot said.

Lightfoot branded as “patently ridiculous” Preckwinkle’s claim that she lacks executive experience.

“I have significant executive experience that’s relevant in running city departments which, frankly, she doesn’t have,” Lightfoot said.

In a race with a 33.5 percent turnout, nearly a record low, Lightfoot finished first with 17.4 percent. Preckwinkle got just over 16 percent.

Between them, Lightfoot and Preckwinkle got about 176,000 votes. But in Round Two, multiple strategists predict a 50 percent turnout; with 1.58 million registered voters, that means the winner will need almost 400,000 votes to win.

That means both candidates must dramatically expand their narrow bases by courting votes that went to Bill Daley, Jeremiah Joyce, Susana Mendoza and Willie Wilson.

Preckwinkle carried only six of the city’s 50 wards, three of them along the south lakefront, which she represented in the City Council for 20 years.

She needs to consolidate a divided labor movement, persuade South and West Side voters who backed Wilson to get over their anger about the now-repealed sweetened beverage tax and aggressively court Hispanics who went for Mendoza and Gery Chico.

“Willie Wilson did pretty well. That hurt Toni tremendously. … This will be more of a challenge for Lori. Toni has longer-established relationships. This is where her institutional support with establishment aldermen and with unions, particularly public employee unions, is especially helpful,” another strategist said.

The Chicago Federation of Labor, which has an ownership stake in the Chicago Sun-Times, took a pass on the mayor’s race in Round One, unable to garner the required two-thirds vote for any of the 14 candidates. The CFL meets again Monday, and Preckwinkle has “a shot” at convincing the organization to get off the fence and stand with her, CFL President Bob Reiter said.

But don’t count on it, he added.

“We may take a position. We may not. I have no idea how this thing is gonna shake out. This wasn’t the runoff people expected,” Reiter said, apparently referring to Daley’s third-place finish.

“These people have more of a relationship with Preckwinkle. She’s more of a known quantity. She’s been an alderman. She’s been county board president. Folks have negotiated collective bargaining agreements with her. She’s worked on public policy and development with the county. There’s more of a record for Toni to speak from. But I don’t know that anyone particularly has a dislike for Lori Lightfoot either. I don’t know that there’s a visceral, `We need to be against Lori,’ [which] would be one of the motivating factors to pick a side.”

Lightfoot carried 11 wards, including the reform-minded north lakefront.

Her best opportunity to expand her base is with the “two most tax-sensitive chunks of the vote: African Americans and non-college-educated whites,” another strategist said.

“You go on the offensive and say we’re paying a corruption tax when we allow this corrupt property tax system that can be gamed by big business and the wealthy. That’s Toni’s career. Joe Berrios and … more and more service taxes,” the strategist said.

“If [Lightfoot] leans into taxes and corruption and makes those the pillars of a ‘change’ argument, she can win. But, if she can’t get on the air until the last two weeks like she did in the first round, Toni’s got a chance to bury her and sneak by her. This is Lori’s race to lose. But her Achilles heel is, she’s not a very good fundraiser. … She’s got to make this appeal to the business community that she can run the city.”