It's an easy choice
Chicago politics has always rewarded the candidate who understands how to turn an improbable campaign into a referendum on the status quo. Few episodes illustrate this better than the rise of Jane Byrne.
When Byrne announced her candidacy for mayor of Chicago in August 1977, she was widely dismissed as a political curiosity. She had been fired months earlier by Mayor Michael Bilandic, the successor to Richard J. Daley’s formidable political machine. Byrne had little institutional support and almost no financial backing. The conventional wisdom in Chicago politics was that incumbents backed by the Democratic organization did not lose.
Then Byrne did something that every insurgent candidate must eventually do. She created a narrative that captured voters’ frustrations. During the campaign she attacked the city’s patronage system and famously staged a confrontation at Rosie’s, a restaurant on 26th and Wallace, involving an alleged “ghost payroller” on the city payroll. The imagery of machine politics became vivid and understandable to voters. It was a time when everyone tuned into the local news on a nightly basis. A young man from the neighborhood asked her why she was wasting her time since she had no chance of beating Bilandic. She looked him straight in the eye and said that she would beat him. She even prompted him to join her campaign. That incident put her on the map.
Byrne’s biggest break came in January 1979 when Chicago was paralyzed by a massive blizzard. The Bilandic administration appeared overwhelmed by the city’s inability to clear the streets and restore transportation.
The lesson from that race remains relevant today. In a state dominated by one party and one powerful incumbent, an opposition candidate must be able to turn the campaign into a referendum on governance itself.
Dabrowski’s campaign is built around that reality. A longtime policy analyst and fiscal reform advocate, he argues that Republicans must rebuild credibility with suburban voters and urban independents who have drifted away from the party over the past couple of decades. His message focuses on the structural problems that have plagued Illinois for years: pension debt, slow economic growth, population decline, and high taxes. Specifically with the tax burden being above average nationwide, the credit rating among the lowest and pension liabilities are among the highest or the highest in the nation. In addition, the Safe-T Act, which had some good aspects like body cams and police accountability really went off the rails with no cash bail and overly lenient pre-trial releases.
This difference in emphasis matters. Pritzker is a well-heeled political veteran who would prefer to run against a candidate whose appeal is limited to the Republican base. A campaign centered on fiscal competence, economic opportunity and personal safety forces the governor to defend Illinois’ record compared with other states.
Another complication for Bailey is the unusual history of his last campaign. During the 2022 Republican primary, political organizations aligned with Pritzker spent millions of dollars on advertising that effectively boosted Bailey’s standing with Republican voters. The ads attacked Bailey’s rivals from the right. The tactic was widely interpreted as an attempt by Democrats to influence the GOP primary to face a weaker opponent in the general election.
Whether Bailey welcomed that assistance or not, the political damage is real. It is difficult to run as the outsider reform candidate when your last nomination campaign was aided by spending from the opposing party’s governor.
Dabrowski enters the race without that baggage.
Policy substance provides another contrast. Both candidates express support for school choice, an issue that has gained momentum nationally as several states have adopted universal school choice, mostly based on education savings accounts. The two campaigns approach the issue very differently.
Bailey’s position is generally supportive but vague. He has endorsed expanding school choice and reviving scholarship programs like Illinois’ former Invest in Kids initiative, which was scuttled by Pritzker. Yet his campaign has offered relatively few details about how such a system would work statewide.
Dabrowski has taken a more explicit position. He supports a universal school choice system that would allow education funding to follow students to private schools, charter schools, or other educational options. His argument is rooted in data. The Chicago Public Schools (CPS) spend close to $25,000 per pupil annually while producing academic outcomes that show high graduation rates but far below scores on math, reading and college readiness. Meanwhile many private and religious schools operate at about one-third the cost overwhelmingly achieving better results, especially among students from poor families.
This contrast allows Dabrowski to frame education reform not merely as a cultural issue but as a fiscal and performance issue. That framing has greater potential appeal among suburban and independent urban voters who may not identify with partisan ideological battles but are deeply concerned about school quality and property taxes.
The fiscal debate offers an even larger opportunity.
Illinois’ financial position remains one of the weakest in the nation. The state carries roughly $140 billion in unfunded pension liabilities and has long ranked near the bottom of national fiscal health studies. Recent budgets have improved due to Covid related bailouts and credit ratings have stabilized, the underlying structural problems remain unresolved.
Dabrowski has spent years studying those issues as a policy researcher. His campaign emphasizes the long-term consequences of Illinois’ pension obligations, which crowd out spending on education, infrastructure, and public safety while contributing to some of the highest property taxes in the country.
That focus presents a direct challenge to Pritzker. The governor has improved the state’s short-term finances, due entirely to the Covid era but has largely avoided major structural reforms to the pension system. A candidate fluent in the details of Illinois’ fiscal architecture (Dabrowski) could turn the campaign into a referendum on whether incremental improvements are sufficient to address decades of accumulated debt.
Bailey’s campaign has criticized Pritzker’s policies but has rarely engaged at that level of policy detail. In a race against a well-funded incumbent, general criticism is unlikely to be enough to capture wavering voters.
Political campaigns often hinge on narrative. Byrne succeeded in 1979 because she convinced voters the city needed a different kind of leadership at a moment of visible failure. For Illinois Republicans in 2026, the challenge is similar. They must persuade voters that the state’s long-term trajectory of slow growth, population loss, and mounting pension obligations requires a major change in direction.
That argument will not be won through ideological slogans alone. It requires a candidate who can speak fluently to both suburban voters and urban yuppies, explain complex fiscal problems in plain language, and present a credible reform agenda.
Ted Dabrowski is far better positioned to so. He spent years at the Illinois Policy Institute doing it.
If Republicans hope to make the 2026 gubernatorial election competitive, they would be wise to remember the lesson of Jane Byrne’s campaign nearly half a century ago that insurgent candidates win not by shouting the loudest, but by redefining the debate.
Illinois’ problems are structural and long-term with a heavy dose of corruption. The Republican nominee should be someone prepared to challenge those issues with equal seriousness. Ted Dabrowski is far superior to Darren Stevens. Pardon the Freudian slip. I meant to say Darren Bailey. If Ted can win the primary, with a pinch of luck he might even win the general election. I wouldn’t count on a blizzard in early November but something else that is unexpected might pop up.
