As he basked in the revelry of his reelection victory Tuesday night, Mayor Daniel Biss reminisced when asked to think back 21 years to his formative political days.
He posited that the young man who pounded on doors for John Kerry in 2004 would be ecstatic at his future win.
“That 27-year-old guy would be surprised and excited,” the mayor told The Daily. “But I also think he would be proud to see his future self running a campaign on his values, leaned in on tough issues because they were important for key priorities like sustainability, affordability — rather than playing it safe.”
Throughout his reelection campaign, Biss emphasized that risk-taking sensibility. And as Biss’ time in office grows, his risk-taking ethos has increasingly served as a recipe for political longevity.
Biss’ blockbuster victory came despite the efforts of challenger Jeff Boarini, who campaigned vigorously against Biss and his sweeping plans to overhaul city policy.
One such plan — Envision Evanston 2045 — drew an organized opposition from residents who scorned its brisk pace and argued its proposals to rewrite the city’s zoning code seemed half-baked and even nefarious.
In his victory speech delivered to cheering supporters Tuesday evening, the mayor highlighted that dispute as a chief challenge he grappled with during his campaign. And before he name-dropped Envision Evanston, he hinted at the fractious nature of those debates that raged while he campaigned.
“It was a little cynical,” Biss said. “It was a little grumpy. It was a little suspicious. And maybe even a little change-averse.”
The mayor’s itch for change dates back even earlier than his political genesis as a young campaigner.
Biss grew up in Bloomington, Indiana, a college town not unlike Evanston where he learned to juggle several things at once. Literally so: He learned the art, joined a circus and even now still occasionally juggles flaming torches.
“I still bet that I’m the only person on here who ever had a paid job on a circus,” Biss told the City Council dais in April 2024. “Not a metaphorical circus.”
The onetime circus artist turned his attention to the nebulous world of mathematics, which he taught at the University of Chicago from 2002 to 2008.
By then, the former mathematician had already pivoted to honing his political calculus, one derived from his stumping for Democratic presidential hopeful Kerry in 2004. Biss moved to Evanston in the following years and developed a reputation as a grassroots left-wing organizer.
Though he lost his bid for a state House of Representatives seat in 2008, he kept knocking on doors. Biss won the seat in the next cycle. And two years after that, he won a state Senate seat anchored in Evanston.
Soon he set his sights on something larger.
In 2017, Biss announced his campaign for governor. Apparent flaws in his mathematical work came to light during the race, when the Chicago Sun-Times jokingly questioned his “math prowess” as “pi in the sky.”
The reform-minded Biss ultimately lost the Democratic primary to now-Gov. JB Pritzker, taking second place.
Biss then turned his focus back to Evanston — successfully — by launching a campaign for the mayoralty. He won a landslide victory in 2021.
During the ensuing four years, the mayor has spearheaded initiatives intended as social reforms and remedies for issues like cost of living. He’s touted implementing ideas like a community responder initiative and a small guaranteed income program. And at his keystone stump speech in January, he vowed further “bold experimentation” in his next term.
That experimentation had already ruffled feathers.
In 2023, as Northwestern’s bid to rebuild and commercialize its football stadium lurched toward City Council, many Ryan Field neighbors organized in staunch opposition to NU’s plans to use it as a public concert venue.
When the zoning change necessary for those plans came down to an initial vote, the council settled on a tie. Biss had to break it. He did so in NU’s favor.
A furor erupted over his decision, leading to the creation of the “Better than Biss” opposition campaign by Parielle Davis, who has declared victory in the 7th Ward City Council race. And some in that north Evanston ward would always scorn the mayor for his decision, even though he often touts the resulting benefits pact with the University as historic.
Just as the dust settled on that dispute — and the dust rose on NU’s stadium rebuild — another Biss tiff loomed.
In February 2024, the mayor helped inaugurate the public process for Envision Evanston. The combined new comprehensive plan and rezoning pledged to set the Evanston agenda for the next two decades, proposing, for example, to eliminate single-family zoning.
Biss served as a prominent surrogate for the city’s push, even once calling it “immoral” for Evanston not to move quickly to adopt it. He had originally pushed for the city to finalize and adopt its plans by April 1 — Evanston election day.
Amid the uproar, City Council decided to slow the process down in January. Boarini, Biss’ challenger, lauded the decision and seized the opportunity to tell Biss “that honestly listening to constituents is better than lecturing them on morality.”
Yet Biss, too, lauded the council’s decision as wise. Ever a political tactician, Biss likely “calculated” that it would have to take longer, former mayor Steve Hagerty told The Daily at the time.
That sort of political calculation — and the occasional triangulation — has indeed proved critical in making Biss’ risk-taking brand feasible. In other respects, however, Biss has shrouded his political rise in an eclectic mystique.
Aside from occasionally bringing out the flaming torches, Biss has frequently remained mum about his ambitions. Before he announced in August 2024 that he would run for reelection, he often insisted he had yet to even decide on running for another term.
He delivered that insistence with the knowing wink of a circus showman. As he delivered his State of the City address in May 2024, he joked that a city initiative to fund campaigns would attract challengers.
“This was like an anti-incumbent mayor initiative, basically,” he told the largely supportive crowd. “So get your petitions ready.”
Boarini, who emerged as his only challenger, had pledged to herald a new era of accountability in Evanston. But come election day, voters largely looked past his message and instead bought into Biss’ performance.
On Tuesday evening, Boarini looked out at his supporters assembled in his Davis Street office to pick up the pieces.
“The mayor spoke many fine words, of course, as he often does,” Boarini said. “And I think we should all work very hard to hold him to every single one of them in the future.”
Now, Biss will have four more years to execute the action he so often speaks of. And Biss’ victory also keeps open possibilities for him to keep advancing up the political ladder in Cook County and beyond.
But he’s often sidestepped the question, so the mystique could grow.
Audrey Pachuta contributed reporting.
Email: shungraves2027@u.northwestern.edu
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