With Obamas on sidelines, can Preckwinkle find another Hail Mary pass?

After pulling one rabbit out of the hat — from Chance the Rapper — Toni Preckwinkle was trying desperately to secure two more endorsements that could have been game-changers: Barack and Michelle Obama.

But the former president and first lady decided to remain on the sidelines and avoid alienating a mayor whose support they need to deliver the Obama Presidential Center in Jackson Park.

Thursday’s announcement by Obama’s office is another blow to Preckwinkle, who yanked her television commercials off the air for at least part of the crucial home stretch.

It’s yet another sign that a runoff race that has been Lori Lightfoot’s to lose ever since she finished on top in the first round of balloting appears headed for a Lightfoot landslide, propelled by a rainbow coalition akin to the one that helped Harold Washington become Chicago’s first black mayor in 1983.


But as lopsided as internal polls show the race to be, Lightfoot’s pollster, Jason McGrath, is taking nothing for granted.

“There were polls out a month or six weeks before [Feb. 26] that had Lori at two or three percent. We are all, to a person, inside the Lightfoot campaign able to remember those days and realize that races change and change quickly,” McGrath told the Sun-Times this week.

“We are not taking our foot off the gas. We are running against somebody who has proven her capacity to win countywide multiple times and who has had several lives in politics. We don’t think this race is over.”

Three political strategists with ties to neither candidate agreed that, barring an “earth-shattering development,” the runoff is likely to be a Lightfoot laugher, the seeds of which were planted weeks before the first round of balloting on Feb. 26.

That’s when mayoral candidate Susana Mendoza, whom polls once showed headed for a runoff against Preckwinkle, started hemorrhaging support because of her ties to disgraced aldermen Edward Burke (14th) and Danny Solis (25th).

Brown paper covers the windows of Ald. Edward Burke’s office at Chicago City Hall, on Nov. 29. | Ashlee Rezin/Sun-Times file photo

“It all collapsed in the last two weeks. The Sun-Times endorsement had something to do with that. Lori Lightfoot getting on TV had something to do with that. The altercation [Lightfoot had] with Martwick had something to do with it,” one political strategist said, referring to state Rep. Robert Martwick, D-Chicago, a Preckwinkle ally. He showed up at a Lightfoot press conference and got into a shouting match with the candidate over a bill Martwick had introduced.

“All of these change voters, particularly on the North Side, moved en masse to Lori. … The fact that the FBI investigation framed this around corruption played into Lori’s hands. Once you got into the second round, this momentum that started before the first round never stopped. Toni was trying to stand in the way of a wave and just couldn’t do it.”

Preckwinkle limped into the runoff with a campaign in disarray, having fired her chief of staff, chief of security and campaign manager.

Her only chance was to go negative and try and define Lightfoot before Lightfoot had a chance to define herself.

But the strategy backfired. Lightfoot responded quickly to the attack. And Preckwinkle was firing blanks.

“Lori’s election night speech was positive, change-driven and inclusive. Toni’s was an angry, nasty political speech that just reinforced…that she was an old school, vindictive, nasty boss of the bosses,” one strategist said.

Toni Preckwinkle

Mayoral candidate Toni Preckwinkle speaks at her election night event at Lake Shore Cafe, 4900 S. Lake Shore Dr., Tuesday night, Feb. 26, 2019. | Ashlee Rezin/Sun-Times

“The coup de gras was this very ill-advised and transparent complimenting her [during their first debate] for being openly gay. It was a huge mistake. The momentum was moving before and everything Toni did just fed into Lori’s momentum.”

Yet another strategist took aim at a Preckwinkle commercial that sought to portray Lightfoot as a “wealthy corporate lawyer who’s defended the elites in this country” only to “recast” herself as a police reformer despite a record showing otherwise.

“It was a kitchen sink ad that was all over the place. Spread too thin. It wasn’t pointed enough in what they were trying to say. They never made the case for why Lori was not fit for the job,” the strategist said.

The Chicago Federation of Labor’s decision to remain neutral was critical. It denied Preckwinkle, whose biggest backers are the Service Employees International Union and the Chicago Teachers Union, a chance to consolidate support from the rest of organized labor.

That allowed Lightfoot to win endorsements and lucrative contributions from the trade unions that had bankrolled Mendoza’s campaign.

It also freed the Chicago Firefighters Union Local 2 to endorse Lightfoot, along with two Northwest Side aldermen — Nick Sposato (38th) and Anthony Napolitano (41st) — who are former firefighters. That was a signal to white ethnic voters on the Northwest Side to support Lightfoot.

Lightfoot’s bid to expand her political base beyond the North Side and north lakefront was also helped immeasurably by endorsements from millionaire businessman Willie Wilson and 19th Ward Democratic Committeeman Matt O’Shea.

On Feb. 26, the 19th Ward led the city with a 55.8 percent turnout that was 20 percentage points higher than the city at large. Mayoral candidate Jerry Joyce came roaring out of that ward — where he lives — with 9,098 votes.

O’Shea’s endorsement and the signal it sent to police officers and firefighters in that vote-rich ward set the stage for Joyce to do the same.

At the South Side Irish Parade on St. Patrick’s Day, Lightfoot also picked up the endorsement of U.S. Rep. Jesus “Chuy” Garcia, who forced Emanuel into Chicago’s first-ever mayoral runoff in 2015. Hispanic voters could take their cue from Garcia.

Willie Wilson endorses mayoral candidate Lori Lightfoot during a press conference at Chicago Baptist Institute International, Friday afternoon, March 8, 2019.

Willie Wilson endorses mayoral candidate Lori Lightfoot during a news conference at Chicago Baptist Institute International on March 8. | Ashlee Rezin/Sun-Times

Wilson’s endorsement was pivotal and not only because he won 13 majority black wards on the South and West Sides.

It sent a signal to his older, church-based constituency that “contracts and jobs and schools” were more important than their concerns about the fact that Lightfoot is a lesbian vying to become Chicago’s first openly-gay mayor. Never mind the ugly fliers found on car windshields outside black churches last Sunday.

“On the South Side, Toni never really grew beyond her base. … She lost to Willie everywhere else because of the soda tax. Now that Willie’s out of the race, that whole anti-Toni black vote is moving en masse to Lightfoot,” one of the strategists said.

“Then you look at the Latino vote, which is hard to poll. But, it feels like they’re going for change, too. They were heavily for Mendoza. … Now, they’re for Lightfoot. So for different reasons, you have the three major voting blocs and geographic areas all moving to Lightfoot, giving Toni no ability to grow.”

An argument can be made that Lightfoot got lucky when the feds raided Burke’s office on Nov. 29.

You can say she benefited even more on Jan. 3, when Burke was charged with attempted extortion for shaking down a Burger King franchise owner for legal business and for a $10,000 contribution to Preckwinkle’s re-election campaign as county board president.

But luck only goes so far. Lightfoot positioned herself to take advantage of her good fortune.

“She showed a lot of moxie when the campaign was basically all her,” one of the strategists said.

Toni Preckwinkle marches in a 4th of July Parade in her Statue of Liberty costume with then state Sen. Barack Obama, left, and state Rep. Barbara Flynn Currie and Ald. Leslie Hairston. Photo provided by campaign.

Toni Preckwinkle marches in a 4th of July Parade in her Statue of Liberty costume with then-state Sen. Barack Obama (left) and state Rep. Barbara Flynn Currie and Ald. Leslie Hairston. Photo provided by campaign.

Obama’s decision to remain neutral is not surprising. His relationship with Preckwinkle has been a somewhat rocky one.

She takes credit for being the one who challenged incumbent state Sen. Alice Palmer’s petitions, clearing the way for Obama to win the Illinois Senate seat that launched his political career.

But Preckwinkle has also been quoted as saying critical things about Obama in later years, basically suggesting that he was a one-way street who used people like her to get ahead.

More recently, she has criticized the Obamas for refusing to sign a community benefits agreement tied to the Obama Presidential Center and said there’s nothing stopping the city from cutting a deal with surrounding residents without the Obamas.

On Thursday, before the Obamas declared their intention to stay out of it, a Preckwinkle strategist was asked whether he considered the Chance the Rapper endorsement to be a game-changer.

“No. But the next two will be.” Asked if he was referring to the Obamas, the strategist said: “I hope so.”

Now, there will be no Hail Mary, courtesy of the Obamas.  Preckwinkle can only hope she can find another rabbit to pull out of the hat.

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