Darren Bailey: Illinois Politician Faces Unimaginable Family Tragedy
In a heartbreaking turn of events that has shocked Illinois and the nation, Republican gubernatorial candidate Darren Bailey and his wife Cindy are mourning the devastating loss of four family members following a helicopter crash in Montana. Their son Zachary, daughter-in-law Kelsey, and two grandchildren—12-year-old Vada Rose and 7-year-old Samuel—tragically lost their lives in the accident that occurred on Wednesday evening, October 23, 2025.
A Family's Darkest Hour
The Bailey family received the devastating news that no parent should ever have to hear. According to a statement released by the Darren Bailey-Aaron Del Mar campaign, the helicopter crash claimed the lives of four beloved family members in Carter County, Montana, located in the southeastern corner of the state near the borders of South Dakota and Wyoming.
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Amid this tragedy, there is one small measure of relief: the family's 10-year-old grandson, Finn, was not aboard the helicopter and remains safe. The campaign's statement emphasized that "Darren and Cindy are heartbroken by this unimaginable loss" and are "finding comfort in their faith, their family, and the prayers of so many who love and care for them."
Federal investigators from the National Transportation Safety Board (NTSB) and the Federal Aviation Administration (FAA) have opened a formal investigation to determine the cause of the accident. As authorities work to piece together what happened, the Bailey family has requested privacy during this extraordinarily difficult time.
Who Is Darren Bailey?
Darren Bailey, born March 17, 1966, in Louisville, Illinois, is a third-generation farmer and conservative politician who has become one of the most recognizable figures in Illinois Republican politics. A lifelong resident of rural Southern Illinois, Bailey embodies the values of small-town America—hard work, traditional faith, and agricultural heritage.
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Bailey graduated from North Clay High School and earned an Associate of Science degree in agricultural production from Lake Land College. He and his sons operate Bailey Family Farm in Xenia, Illinois, where he learned the principles that would later shape his political philosophy. He has been married to his wife Cindy Stortzum for 39 years, and together they've built a life centered on their motto: faith, family, and farming.
Before entering state politics, Bailey served on the North Clay Board of Education, gaining experience in local governance and community service. This grassroots involvement laid the foundation for his eventual leap into state-level politics.
Political Career: From State House to Statewide Campaigns
Early Legislative Career
Bailey's political journey began in earnest in 2018 when he defeated incumbent David Reis in the Republican primary for Illinois House of Representatives District 109. His victory was notable as it was backed by Dan Proft's Liberty Principles PAC, signaling his alignment with conservative activism. He went on to win the general election with an overwhelming 76.14% of the vote against Democratic candidate Cynthia Given.
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Representing the 109th District in Illinois' Wabash Valley region, Bailey quickly established himself as a vocal conservative voice. The district encompassed all of Edwards, Jasper, Richland, Wabash, Wayne, and White counties, along with portions of Effingham and Lawrence counties—predominantly rural areas that aligned with his agricultural background and conservative values.
In 2020, Bailey successfully ran for the Illinois Senate seat being vacated by Dale Righter, winning both the March primary and the general election. He served in the Illinois State Senate representing the 55th District from 2021 to 2023, where he became known for his outspoken positions on various hot-button issues.
The COVID-19 Controversy That Launched National Attention
Bailey rose to statewide prominence in 2020 through his opposition to Governor J.B. Pritzker's COVID-19 emergency measures. In April 2020, he filed a lawsuit against Pritzker, challenging the governor's stay-at-home order extension as unfairly affecting residents of Clay County. A judge granted Bailey a temporary restraining order, though it applied only to him personally—a decision that drew both criticism and support.
Pritzker characterized Bailey's lawsuit as a "cheap political stunt," and tension between the two politicians would only intensify in the years to come. The controversy reached its peak on May 20, 2020, when the Illinois House voted 81-27 to remove Bailey from its session for refusing to wear a mask, highlighting the deep political divisions over pandemic response measures.
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This willingness to challenge authority and stand up for what he viewed as government overreach resonated with conservative voters frustrated by pandemic restrictions, transforming Bailey from a relatively unknown state legislator into a recognizable political figure.
The 2022 Gubernatorial Campaign
On February 22, 2021, Bailey announced his candidacy for governor of Illinois, positioning himself as a conservative alternative to the billionaire Democrat incumbent, J.B. Pritzker. He selected Stephanie Trussell, a former conservative talk radio host from WLS-AM 890, as his running mate for lieutenant governor.
The Republican primary was competitive, with well-funded candidates like Aurora Mayor Richard Irvin receiving substantial backing. However, Bailey's campaign received an unexpected boost from an unlikely source: Governor Pritzker himself. Pritzker and the Democratic Governors Association ran television advertisements during the Republican primary attacking Bailey as "too conservative" for Illinois—a strategy designed to elevate the candidate they viewed as the weakest general election opponent.
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The tactic worked in Pritzker's favor during the primary. Three days before the primary election, Bailey appeared at a rally with former President Donald Trump and received his coveted endorsement. Bailey went on to win the Republican primary by a commanding margin, securing 57.7% of the vote and winning 100 of Illinois' 102 counties—a stunning display of rural support.
However, the general election proved far more challenging. Bailey's tough-on-crime message and conservative positions failed to gain significant traction in the heavily populated Chicago metropolitan area, which dominates Illinois politics. Pritzker cruised to a decisive 13-point victory, with the race being called within minutes of polls closing. Bailey secured only 42% of the vote statewide and a mere 24% in Cook County, home to Chicago.
Despite outspending Bailey's campaign significantly—Pritzker poured $152 million into his re-election bid—the results highlighted the fundamental challenge facing Illinois Republicans: the state's urban-rural divide makes it exceptionally difficult for downstate conservatives to win statewide office.
The 2024 Congressional Bid
Undeterred by his gubernatorial loss, Bailey returned to the political arena in 2024, this time setting his sights on Congress. He announced a primary challenge to five-term Republican incumbent Mike Bost in Illinois' 12th Congressional District, a solidly conservative district in southern Illinois that Donald Trump won with 56% of the vote in 2020.
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Bailey positioned himself as a more conservative and combative alternative to Bost, whom he suggested was insufficiently aggressive in fighting for conservative values. "I've been out there working and fighting against the adversity and the failures of career politicians, and I'm tired of it," Bailey declared upon announcing his candidacy.
The race put Bailey in an awkward position regarding Trump's endorsement. While Trump had endorsed Bailey in the 2022 gubernatorial race, the former president supported Bost in the congressional primary, calling him a "proud ally" and "terrific representative." Bailey worked to secure Trump's endorsement, noting in one interview that he had told Trump: "He was a congressman the entire time that you were president. And the fact that you don't know if he's the good guy or not, that should say a lot."
The March 19, 2024, primary was closer than many expected, but Bailey ultimately fell short, losing to Bost by approximately 2,700 votes. The narrow margin demonstrated Bailey's continued appeal among grassroots conservatives but also revealed the challenges of defeating well-established incumbents, even within one's own party.
The 2026 Gubernatorial Campaign: A Second Chance
In September 2025, Bailey launched his second campaign for governor, announcing that Cook County Republican Party Chair Aaron Del Mar would serve as his running mate for lieutenant governor. The pairing was strategic, bringing together Bailey's downstate rural base with Del Mar's connections in the Chicago suburbs—an area where Bailey had performed poorly in 2022.
Bailey acknowledged that his 2026 campaign would take a different approach than his previous gubernatorial bid. "This journey is going to look different than it did four years ago," he told supporters at a campaign rally in Bloomington. "We're out to win. We're on a mission."
The campaign kicked off with three stops in one day—Carterville, Bloomington, and Oak Brook—with Bailey traveling between locations via helicopter piloted by his son Zachary, demonstrating the family's involvement in both Bailey's business and political endeavors. The emphasis on connecting with suburban voters represented a clear acknowledgment that winning statewide office in Illinois requires more than just overwhelming rural support.
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Bailey explained his renewed optimism about his chances: "The climate here in Illinois is a lot more obvious and conducive than it was three and four years ago. People have woke up and they've realized that, 'wow, why did we just go through these last three years?' And that they're tired of it."
Despite the painful history between Bailey and Del Mar—they had previously disagreed on political matters—the two decided to put their differences aside. "We put it aside; we let the bygones be bygones," Del Mar explained. "And we came out and we said we're going to run together as a team."
Democrats, meanwhile, showed little concern about facing Bailey again. Illinois Democratic County Chairs' Association President Mark Guethle stated that Bailey's decision to run again is "fine by us!"—a clear indication that they view him as a beatable opponent.
Bailey joins a Republican primary field that includes DuPage County Sheriff James Mendrick, conservative researcher Ted Dabrowski, and Lake Forest businessman Joe Severino. The primary is scheduled for March 17, 2026.
Political Positions and Ideology
Darren Bailey is widely characterized by news outlets and political observers as occupying the far-right of the Republican Party spectrum. His positions reflect deeply conservative views on social issues, government power, and individual liberty.
Abortion and Social Issues
Bailey holds staunchly pro-life views and has consistently opposed abortion rights throughout his political career. He praised the Supreme Court's 2022 decision in Dobbs v. Jackson Women's Health Organization, which overturned Roe v. Wade and returned abortion regulation to individual states. Bailey supports a statewide ban on abortion in Illinois, with an exception only when the mother's life is in danger—opposing exceptions for cases of rape or incest.
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In a 2017 Facebook video that later drew criticism, Bailey controversially stated: "the attempted extermination of the Jews of World War II doesn't even compare on a shadow of the life that has been lost with abortion since its legalization." The comment sparked significant backlash and highlighted the intensity of his views on the issue.
Criminal Justice Reform
Bailey is a vocal opponent of the SAFE-T Act, comprehensive criminal justice reform legislation signed into law by Governor Pritzker. Among other provisions, the law ended mandatory cash bail in Illinois—a change Bailey and many Republicans argue makes communities less safe. Opposition to the SAFE-T Act has become a central theme of Bailey's political messaging and connects to his broader law-and-order platform.
Chicago and Urban-Rural Divide
In 2019, Bailey and seven other Republican legislators sponsored a provocative resolution calling for the City of Chicago to become its own state, separate from the rest of Illinois. The resolution argued that "the majority of residents in downstate Illinois disagree with City of Chicago residents on key issues such as gun ownership, abortion, immigration, and other policy issues."
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While similar resolutions had been introduced before with no real chance of passage—and some sponsors acknowledged they didn't actually intend to follow through—the gesture underscored the deep frustration many downstate Republicans feel about Chicago's dominance of Illinois politics. When Bailey announced his gubernatorial campaign, he backtracked, calling it "an old resolution" and "a warning shot" directed at Chicago rather than a serious policy proposal.
Election Integrity
Following the 2020 presidential election, Bailey declined to acknowledge that Joe Biden fairly defeated Donald Trump. When asked about Trump's claims of voter fraud, Bailey stated he "did not know" if they were legitimate, despite these claims being thoroughly investigated and disproven. This position aligned him with a significant portion of the Republican base that continued to question the 2020 election results.
Personal Life and Values
At the heart of Darren Bailey's identity is his commitment to family, faith, and farming. These three pillars have shaped not only his personal life but also his political philosophy and public persona.
Bailey and his wife Cindy have been married for 39 years, building a partnership rooted in shared values and rural Illinois traditions. Together they raised four children and welcomed multiple grandchildren into their lives. The Bailey family operates Bailey Family Farm, where Darren and his sons work the land much as generations before them have done.
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For Bailey, farming is more than just an occupation—it's a way of life that teaches fundamental lessons about responsibility, hard work, and the relationship between effort and reward. These agricultural roots inform his skepticism of government intervention and his belief in self-reliance and community support over bureaucratic solutions.
Faith plays a central role in the Bailey family's life. They have consistently emphasized their Christian beliefs and the importance of traditional values. In the wake of the helicopter crash tragedy, their faith has become a source of comfort, with the campaign statement noting they are "finding comfort in their faith, their family, and the prayers of so many who love and care for them."
The Path Forward
As Darren Bailey and his family navigate the darkest chapter of their lives, questions naturally arise about the future of his gubernatorial campaign. Political campaigns often fade into insignificance when confronted with personal tragedy of this magnitude. The loss of a child, daughter-in-law, and two grandchildren is a wound that no political victory could ever heal.
The outpouring of support from across the political spectrum demonstrates that even in our deeply divided political era, human tragedy can unite people in compassion. Political opponents and allies alike have expressed their condolences and offered prayers for the Bailey family during this unimaginably difficult time.
Federal investigators will work to determine the cause of the helicopter crash, but no investigation or explanation can bring back the four lives lost. For now, Darren and Cindy Bailey face the painful task of grieving while surrounded by family, friends, and a community that is holding them close.
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Whether Bailey's political career continues, pauses, or ends in the wake of this tragedy remains to be seen. But what is certain is that Darren Bailey the politician has become secondary to Darren Bailey the grieving father and grandfather. The man who spent years in the spotlight debating policy positions and challenging political opponents now faces a challenge no one should have to endure—finding a way forward after losing so much.
The helicopter crash has reminded all of us that behind every political figure, there is a human being with a family they love, dreams they hold dear, and a heart that can break. As investigations continue and time passes, the Bailey family will need space, privacy, and compassion as they process their grief and determine their path forward.
Conclusion
Darren Bailey's story is one of rural American values, political conviction, and now, profound tragedy. From his roots as a third-generation farmer in Southern Illinois to his emergence as a prominent conservative voice in state politics, Bailey has represented a particular vision of Illinois—one rooted in small-town traditions, agricultural heritage, and conservative principles.
His political journey has been marked by controversy, passionate advocacy, and electoral setbacks. Yet he has consistently demonstrated resilience and determination, returning to the political arena even after defeats. His opposition to COVID-19 restrictions brought him to prominence, his 2022 gubernatorial campaign made him a household name across Illinois, and his 2026 campaign represented another attempt to translate rural conservative support into statewide victory.
Now, however, all of that is overshadowed by unimaginable loss. The helicopter crash that claimed four members of his family has reminded us that political differences, campaign strategies, and policy debates pale in comparison to the fundamental human experiences of love, family, and loss.
As Illinois and the nation watch, Darren and Cindy Bailey face the most difficult journey of their lives—one that no political experience could have prepared them for. Their faith, family, and community will be their guides as they navigate the days, weeks, and months ahead. The prayers of people across the political spectrum go with them.
For more news and updates on Illinois politics and other important topics, visit Toolz Mallu Blog for thoughtful analysis and comprehensive coverage.
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