Did Lori Lightfoot bet on Chicago teachers strike? Email lays out Scotch-and-cigars wager, but mayor and top aide deny bet.

Two days before the Chicago Teachers Union officially went on strike in 2019, one of Mayor Lori Lightfoot’s top aides sent her a note about what he called “The Bet.”

In the email, Lightfoot senior adviser and legal counsel Michael Frisch laid out a wager and its stakes.

“The Bet: 3 cigars and a bottle of scotch of the winner’s choosing. Under: Strike ends before next Weds. Over: Strike extends past Weds,” Frisch wrote in the email, which had “confirming our agreement” in the subject line.

Referencing Lightfoot’s chief of staff, Maurice Classen, who was also on the email, Frisch added, “Frisch and Maurice have the Under, MLL has the Over. Now no one can back out ...”

Neither Lightfoot nor Classen responded to the email, according to what Lightfoot’s office released. A Lightfoot spokeswoman said the mayor “does not have any recollection of the email in question” but took the CTU strike “very seriously” and “of course never participated in any bet nor would she.”

During the strike, which lasted for roughly two weeks, Frisch served as a high-ranking member of Lightfoot’s bargaining team. In response to follow up questions, including why Frisch thought there was a bet, the Lightfoot administration released a statement on his behalf apologizing.

“My email reflected a failed attempt on my part to inject some levity into a high stress, tense and serious situation,” Frisch said. “There was no actual bet--this was intended to be a joke that clearly did not land. It was in poor taste, and I apologize.”

Much of Lightfoot’s tenure has been marked by conflict with CTU, and the email is unlikely to improve the relationship.

News of the email also comes at a time when union officials complain that Lightfoot’s team at Chicago Public Schools hasn’t worked with them enough on potential coronavirus pandemic reopening plans.

Told of the email, CTU vice president Stacy Davis Gates said “this is the type of irreverence the mayor and her CPS team demonstrate all the time.”

“If this is how the mayor and her leaders behave when no one is looking it’s no wonder it is taking us so long to agree on a credible safe plan to reopen our school buildings or to make remote learning more sustainable for students, their families, and school staff,” she said.

During her run for mayor, Lightfoot campaigned on a pledge to “bring in the light” and promised to boost transparency at City Hall and reform local government. Since taking office, however, Lightfoot has faced criticism over her handling of some key open government issues and her administration sought to keep secret Frisch’s email that mentioned the bet.

Previously, the Illinois Attorney General’s office ruled the City Council violated the state’s open meetings law when it held a series of conference calls with Lightfoot during the early days of the coronavirus pandemic. Lightfoot also has repeatedly refused to release the inspector general’s report on the night former police Superintendent Eddie Johnson was found asleep in his car after drinking at a downtown bar known for heavy pours, despite calls from activists, media outlets and some aldermen to do so.

In this case, the mayor’s office redacted Frisch’s email while denying a Tribune open records request, citing exemptions to the Illinois Freedom of Information Act that protect policymaking discussions and attorney-client privilege.

But the Illinois attorney general’s office ruled late last month that the city improperly withheld the email and ordered its release.

Ben Silver, an attorney with the Citizen Advocacy Center in Elmhurst, said the city’s actions in hiding the email could create credibility issues for the administration.

“When you see a situation like this where they’re pretty clearly abusing the exemptions, essentially to cover up something that’s going to be embarrassing, it usually amplifies the problem by the time you get to the bottom of it,” Silver said. “You take an embarrassing situation and turn it into a problem of public trust.”

David Melton, a senior adviser at watchdog group Reform for Illinois where Lightfoot was previously a board member, agreed that the city misused FOIA exemptions to withhold the email.

“It sounds to me like it was a silly personal thing that they should’ve just owned up to and produced it,” Melton said.

Although Lightfoot through a spokeswoman denied betting on the strike, she has publicly acknowledged her appreciation for scotch and cigars. Most recently, Lightfoot said she would celebrate the City Council passing her budget with a scotch, a cigar and a steak.

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Lightfoot isn’t the first Chicago mayor to have a contentious relationship with CTU. The union went on strike during former Mayor Rahm Emanuel’s tenure, and he famously told CTU president Karen Lewis “f--- you” during a meeting.

But Lightfoot has had an especially contentious relationship with the union. The CTU endorsed Lightfoot’s opponent, Cook County Board President Toni Preckwinkle, in the 2019 mayoral race and spent hundreds of thousands of dollars against her.

Since Lightfoot’s win, the union has repeatedly criticized her for failing to live up to progressive campaign promises, accusing her of campaigning one way but governing another. In turn, Lightfoot has accused the union of attempting to harm her politically by propping up her critics.

CTU’s strike last year marked the longest since the 1980s, and ended bitterly when Lightfoot refused to allow teachers to make up all their strike days.

During a post-strike interview with the Tribune, Lightfoot said the union was going to walk out “no matter what,” and said she expects the CTU to “come after” her in 2023.

The back and forth over labor issues also has continued into 2020. CTU threatened to strike if Lightfoot reopened schools for in-person learning to start the new year.

This past June, Lightfoot lambasted as “clearly racist” and “deeply offensive” a tweet by the union depicting an apparent cartoon version of her tied up, wearing a police uniform and being unmasked by the characters from the “Scooby-Doo” TV show.

The tweet depicted the Black mayor bound with rope, surrounded by the white characters, who have taken a cop mask off her head to reveal that the officer is actually Lightfoot. It’s a play on the scene at the end of each episode of the Hanna-Barbera cartoon, when the team of youngsters would solve the mystery by unmasking a villain to show it was actually a person they’d met earlier in the episode.

Then, on Election Day this year, Lightfoot mixed it up with an activist outside a Far North Side polling place over Cook County Judge Michael Toomin, who was up for retention but opposed by the Cook County Democratic Party led by Preckwinkle.

In a scene captured on a video posted to Twitter by teachers union activist Mary Difino, Lightfoot approached Difino after she criticized Toomin’s candidacy for retention. Lightfoot repeatedly stepped toward Difino and said, “You’ve got your facts wrong, you’ve got your facts wrong.”

Two members of Lightfoot’s security detail then stepped between Lightfoot and the activist as the mayor pointed her finger toward Difino and added, “Your teachers union is wrong about that.”

A CTU spokeswoman later said the union doesn’t endorse judicial candidates.

gpratt@chicagotribune.com

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