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Alderman Brendan Reilly weighs a challenge to Boss Toni
First came Ellen Burke, a no-nonsense former prosecutor who bucked the machine, defeated Toni Preckwinkle’s handpicked candidate for Cook County State’s Attorney, and then stormed to victory in the general election. Burke's win was not just a local upset — it was a seismic tremor through the iron-fisted rule of Preckwinkle’s county Democratic apparatus.
Now comes Brendan Reilly, an Irishman in the same reformist mold, who appears ready to challenge Preckwinkle herself. And not for a side office or down-ballot seat. No, Reilly is eyeing the throne: Cook County Board President.
This would be the most serious challenge Preckwinkle has faced in years. It may be the only serious threat she’s ever faced politically.
“There’s a mood for change,” said Reilly in a recent interview with NBC Chicago. And he’s right. You can feel it. The Preckwinkle machine — once efficient, feared, and firmly entrenched — now feels stale, sluggish, and out of sync with the public. After nearly 15 years as Board President, Toni Preckwinkle wants a fifth term. Brendan Reilly is thinking: Enough is enough.
A real race for a real office
Preckwinkle has become something like Cook County’s monarch, presiding over an empire that controls the courts, the jails, the State’s Attorney, and the judiciary’s vast administrative infrastructure. This isn’t a ceremonial post — it’s power with a capital “P.” And that’s exactly why Reilly’s challenge matters.
“This is an office that hasn’t had a real contest in several terms,” Reilly said, noting that voters deserve more than a rubber stamp or a coronation. “It’s not something that should just be inherited.”
Reilly is no political dilettante. He represents Chicago’s 42nd Ward — Downtown, River North, Streeterville, the Loop — an area that includes the city’s financial core and most of its high-rise tax base. Reilly has served as alderman since 2007 when he ousted 36-year incumbent Burton Natarus, a man deeply embedded in the old-school Chicago ward boss tradition. Reilly won that race with organization, discipline, and a reputation for being the rarest of creatures in city politics: Rational.
In other words, this isn’t his first insurgency.
Common sense versus the machine
If Burke represented a revolt from the prosecutorial class against Preckwinkle’s “decarceration at all costs” ideology, Reilly represented a middle-class, business-friendly revolt from the heart of the city. The people who keep Chicago running — those who work in high rises, pay the taxes, and fund the infrastructure — are increasingly fed up with the ideological overreach of the Preckwinkle era.
It’s not just about policy. It’s about priorities.
Preckwinkle spent years backing Kim Foxx, the now-departed State’s Attorney whose policies left thousands of victims without justice. She supported judicial candidates who took a dim view of law enforcement and a shockingly sympathetic view of repeat offenders. Under her watch, the jail population plummeted — but not because crime disappeared. Crime exploded. The accountability system collapsed.
Now Boss Toni wants to stay the course.
Reilly’s camp is betting that voters — especially Democrats — want a correction. Not a Republican shift, but a pragmatic one.
And in Cook County, that starts at the top.
The county’s outsized role in public safety
Why does this matter so much to Chicagoans? Because Cook County doesn’t just run the suburban forest preserves. It controls the justice system — the State’s Attorney, the court system, the judges, the pretrial release policies, the public defender’s office, and, crucially, the jail itself.
In fact, if you had to rank law enforcement power in Chicago, you might put the Cook County State’s Attorney and Chief Judge right up there with the Superintendent of Police.
And who sets the budget for all of it? Who determines the administrative appointments? Who decides how those departments are staffed and funded? The County Board. More specifically, it’s the President.
If you want a functioning justice system in Chicago, it’s not enough to fix the police department. You have to fix the county.
That’s why Reilly’s candidacy could matter more than any mayoral race in the next five years.
Reilly’s appeal isn’t limited to the Loop. He has long enjoyed support from neighborhood groups in Streeterville and Gold Coast who are frustrated by crime creeping into their once-safe streets. But his interest in running was sparked in part by outreach from a broader coalition — business leaders, suburban mayors, and even some fellow elected officials — who see Preckwinkle’s long tenure as a liability heading into 2026.
They’re not wrong.
Preckwinkle’s time as head of the Cook County Democratic Party has been marked by a number of high-profile embarrassments:
- The collapse of the Foxx-backed prosecution system
- Her failed bid for mayor in 2019
- The bizarre endorsement of a Socialist candidate for City Council who openly supports police abolition
- And most recently, her near-total political isolation after the Burke victory
For years, Preckwinkle has ruled by default. That may finally be ending.
Reilly offers voters something rare in Chicago politics: A leader who isn’t insane. Reilly is not a radical leftist, nor is he a phony moderate. He doesn’t speak in academic jargon. He listens to constituents, respects business, and wants functioning institutions.
Imagine that.
A natural fit for the job
If Reilly runs, he’ll do so as a Democrat. And he’ll need to win the Democratic primary to have a real shot. That’s no easy task: Preckwinkle controls the party apparatus, many of the ward organizations, and still wields considerable influence over campaign cash.
But there are cracks.
Preckwinkle's grip on the party has slipped in recent cycles, especially after her failed mayoral bid and Foxx’s exit. She’s seen as out of touch by younger progressives and too radical by traditional liberals. In other words, she may be stranded between factions, without the coalition she once commanded.
Reilly, by contrast, has kept his independence. He votes his ward. He talks like a grown-up. He still gets invited to fundraisers in the Gold Coast and the 19th Ward alike.
That makes him dangerous.
Preckwinkle of course has the same advantages as “Mayor” Brandon Johnson: The Chicago Teachers Union political cadre and the slander machine that will try to paint lifelong Democrat Reilly as a MAGA Republican. Reilly’s brain trust needs to study Paul Vallas’ mayoral campaign for lessons learned on how to successfully challenge this canard.
If there’s one office where competence matters more than ideology, it’s County Board President. Because when jails overflow, cases pile up, and courts grind to a halt, it doesn’t matter how progressive your press releases are. People want order.
Preckwinkle had her moment. It lasted 15 years. But the voters — especially the exhausted, overtaxed, crime-weary voters of Chicago — may finally be ready to try something new.
Or maybe, just maybe, something old.
Like an Irishman with a spine.
