The Man Who Could End Pritzker’s White House Dream

From farm fields to the Statehouse, Darren Bailey may be preparing the fight of his life — one that could shake American politics far beyond Illinois.

By Mike Monseur
September 9, 2025

The morning sun breaks over the flat expanse of southern Illinois, painting the fields in gold. Darren Bailey, tall and broad-shouldered, walks slowly between rows of soybeans still slick with dew. His boots carry the dirt of four generations. His grandfather walked these same rows. So did his father. Now Bailey and his wife, Cindy, along with their sons — Zach, Cole, and Mason — carry on the work.

To the Baileys, farming is not just planting and harvesting. It is stewardship. It is faith. It is family. And it is heritage. They rotate crops, conserve the soil, and embrace new technology not to grow rich, but to stay rooted.

“With faith, service, work ethic, and integrity, we may find real prosperity,” Bailey says.

That mix of faith and grit first propelled him into politics. It carried him from the farm to Springfield — and now, according to sources close to him, it may push him once more into the governor’s race. A contest that could pit a farmer against one of America’s wealthiest governors and, in the process, derail J.B. Pritzker’s rumored presidential ambitions.

From Fields to Springfield

Bailey entered the Illinois House in 2018 as a political outsider. He wasn’t polished. He wasn’t cautious. He spoke the way he did on the farm: plain, direct, and sometimes blunt enough to make his colleagues wince.

But voters recognized him. When Governor Pritzker issued sweeping pandemic orders, Bailey was the one who sued him in court. When Democrats celebrated the SAFE-T Act, Bailey warned it would endanger neighborhoods by eliminating cash bail. He fought for lower taxes, smaller budgets, and school funding fairness for rural Illinois.

In 2020, he moved to the State Senate, where he continued to stand as a rural voice in a chamber dominated by Chicago Democrats. His critics called him inflexible. His supporters called him principled. Either way, he became impossible to ignore.

The First Showdown

By 2022, Bailey had become the face of downstate conservatism. He rode grassroots energy — and an endorsement from Donald Trump — to the Republican nomination for governor.

The general election, however, was brutal. Pritzker’s billions and Chicago’s Democratic machine crushed Bailey’s campaign, handing the governor a 13-point victory. Bailey was outspent, outmuscled, and written off by many in his own party.

But unlike most losing candidates, he didn’t fade away. He sharpened his message, warning that crime was rising, taxes were suffocating, and families were leaving Illinois in droves. And as Pritzker’s name began surfacing in conversations about the White House, Bailey’s voice grew sharper still.

“JB has been a disaster for Illinois. Families are struggling, businesses are leaving, and crime is rising, yet he’s chasing his dream of the White House,” Bailey declared in a recent post.

The Second Chance

Now, according to insiders, Bailey is preparing to try again. If he does, Illinois could see a rematch — the farmer vs. the billionaire — but this time with higher stakes.

Whispers suggest Bailey is considering a bold choice for running mate: Aaron Del Mar, the new chairman of the Cook County Republican Party. Del Mar, a businessman and organizer, has been tasked with the impossible job of rebuilding Republican credibility in Chicago. Pairing Del Mar’s suburban and urban network with Bailey’s downstate base would signal something Illinois Republicans have long avoided — a plan to compete everywhere, not just in the heartland.

A Party Problem

But Bailey knows the hardest fight may not be against Pritzker at all. It may be against his own party.

In 2022, Illinois Republicans gave Bailey the nomination but little else. Many insiders whispered he was too conservative, too rural, too unelectable. Meanwhile, Democrats poured more than $100 million into voter turnout operations. The result was inevitable.

Thomas DeVore, a conservative attorney who has long criticized Republican leadership, says Bailey was never the problem.

“It was not because Bailey was the wrong candidate. It was because Illinois Republicans lack the leadership, resources, and strategy to win statewide.”

Unless the GOP builds infrastructure — money, organization, boots on the ground — Bailey may again be left to fight with passion alone against a machine built on money and manpower.

What Illinoisans Say

On a farm outside Effingham, a man leaned against his pickup, sun hat shading his face, and spoke with quiet conviction. “He’s one of us,” he said of Bailey. “He fought for us in Springfield when nobody else would. He knows what it’s like to pay property taxes so high you can’t breathe.”

Up in DuPage County, a mother balancing grocery bags in a strip mall parking lot sighed. “I like Bailey,” she admitted, “but unless Republicans figure out Cook County, I don’t see how he wins. Chicago decides everything.”

And on Chicago’s South Side, a weary father sat on his porch steps after work. “The Democrats show up for our votes, then vanish,” he said. “Bailey doesn’t pretend the crime isn’t real. At least he’s talking about it.”

Three voices, three corners of Illinois — loyalty, skepticism, frustration. Together, they capture the paradox of Bailey’s candidacy.

A State at a Crossroads

The backdrop for Bailey’s possible campaign is stark. Property taxes remain among the highest in the nation. Illinois has lost more than 100,000 residents in the past decade. Chicago’s homicide rate still ranks among America’s worst. Businesses continue to flee to Indiana, Texas, and Florida.

For Bailey, these are not statistics. They are stories. Neighbors forced to sell farms that had been in their families for generations. Small businesses shuttered after decades of work. Children leaving Illinois because they no longer see a future here.

“Chicago should be a beacon of hope and prosperity,” Bailey insists. “Instead, under JB Pritzker, Mayor Johnson, and the Democrats, the city has become a haven of crime and chaos.”

Billionaire vs. Farmer

If Bailey announces, Illinois will once again see a contest of opposites. Pritzker is a billionaire heir, a Democratic megadonor, a man of skyscrapers and national ambition. Bailey is a fourth-generation farmer, a husband, father, and legislator, shaped by faith and rooted in soil.

It is more than an election. It is privilege against persistence. Machine against grassroots. Skyscraper against farmhouse.

The Stakes Beyond Illinois

What happens in Illinois will not stay there. If Pritzker is serious about a 2028 presidential bid, a loss to Bailey would cripple his ambitions before they begin. For conservatives, Bailey represents not only Illinois’ best hope for change, but also the chance to stop Pritzker from carrying his brand of politics onto the national stage.

The Test of Belief

Bailey has not yet declared. Del Mar has not yet been confirmed. The Illinois GOP remains fractured. But the signs are unmistakable: sharper critiques, whispered alliances, and the restless determination of a man who has never stopped fighting.

If he runs, it will be Bailey against more than Pritzker. It will be Bailey against the machine. Bailey against his own party’s inertia. Bailey against voters taught to believe that nothing can change.

And perhaps that is why this race matters more than most. Because Darren Bailey’s story — the farmer who became a legislator, now preparing to challenge a billionaire — asks a larger question: can ordinary people still reclaim their democracy from the grip of money and entrenched power?

One day soon, Bailey may walk out of his fields at dawn, the soil clinging to his boots, and lift his eyes north toward the shimmering skyline of Chicago. In that moment, the contest will no longer be about a governor’s office. It will be about whether a farmer, armed with faith and grit, can stare down the machine — and whether Illinois still belongs to the people who work its land, or to the billionaires who rule its towers.

Sources

Illinois General Assembly – official member profiles and legislative record.
Illinois State Board of Elections – certified 2022 election results.
U.S. Census Bureau – Illinois population and outmigration data.
Illinois Department of Revenue – property tax statistics and reports.
Illinois State Police and Chicago Police Department – annual crime reports.
Governor J.B. Pritzker’s official office – COVID-19 executive orders, SAFE-T Act signing.
Darren Bailey biography: Ballotpedia, Bailey for Illinois.
Aaron Del Mar background: Cook County GOP.
Commentary from Thomas DeVore: public statements and social media posts.
Bailey’s recent public statements: official Facebook campaign posts.
FactsFirstUS.com Investigative Unit: reporting and analysis on Illinois GOP infrastructure and election challenges.