Four members of Illinois Republican gubernatorial candidate Darren Bailey’s family perished on Wednesday, October 22, 2025, when their helicopter crashed in Montana, sending shockwaves through the political community and prompting an outpouring of sympathy from both sides of the aisle.
Bailey’s son Zachary, his daughter-in-law Kelsey, and two of their three children—Vada Rose, 12, and Samuel, 7—were killed in the accident near Ekalaka, Montana, according to a campaign statement released early Thursday morning. The couple’s 10-year-old son, Finn, was not aboard the aircraft and survived.
Zachary Bailey was piloting the helicopter at the time of the crash, a role he frequently assumed for his father’s campaign events and the family’s farming operations. Carter County emergency services responded to the scene at 7:22 p.m. Wednesday evening, though specific details about the circumstances surrounding the crash remained limited as of Thursday.
The National Transportation Safety Board announced Thursday morning via social media that it was investigating the crash of a Robinson Helicopter R66 in the southeast portion of Montana. The agency has not yet released information about what caused the aircraft to go down.
In a statement posted to social media, the Bailey campaign expressed the family’s profound grief. “Darren and Cindy are heartbroken by this unimaginable loss,” the statement read. “They are finding comfort in their faith, their family, and the prayers of so many who love and care for them.”
The family requested privacy as they mourn and process the devastating loss. Bailey, 59, and his wife Cindy have four children and 13 grandchildren total. Zachary, along with his brothers Cole and Mason, operated Bailey Family Farm alongside their father, representing the fourth generation of farmers working the land in southern Illinois.
Bailey currently serves as a Republican candidate for governor in the 2026 election, his second attempt at the state’s highest office. He secured the Republican nomination in 2022 but lost to Democratic incumbent JB Pritzker in what became one of the most expensive non-presidential races in American history, attracting tens of millions of dollars in donations and spending from both campaigns.
Before his gubernatorial runs, Bailey served in both chambers of the Illinois state legislature, representing portions of southern Illinois. He also mounted an unsuccessful campaign for the U.S. House of Representatives in 2024, narrowly losing the Republican primary for Illinois’ 12th Congressional District. His current running mate for the 2026 gubernatorial race is Aaron Del Mar, who chairs the Cook County Republican Party.
Political figures across Illinois, including Bailey’s opponents, expressed condolences following news of the tragedy. Governor Pritzker, who defeated Bailey in 2022, became emotional at a Thursday news conference in Chicago while discussing the loss. He reflected on losing his own parents at a young age and indicated he could not imagine experiencing the death of a child and grandchildren.
Pritzker and his wife released a joint statement expressing devastation over the news and extending prayers and deep condolences to the Bailey family. He emphasized that the family’s memories of their loved ones should serve as a blessing during this difficult time.
Ted Dabrowski, one of Bailey’s Republican opponents in the 2026 race, also issued a statement acknowledging the family’s loss. He indicated that he and others grieve alongside the Baileys and expressed confidence that the family’s deep faith and strong familial bonds would provide support during their mourning.
Bailey’s campaign website describes him as a farmer, family man, and citizen from rural Illinois whose conservative roots run deep. The Bailey Family Farm website emphasizes the family’s dedication to stewardship of the land and notes that working together as a family has been essential to building their lasting heritage.
The tragedy occurred just days before candidates for office in 2026 were scheduled to begin submitting petitions to the State Board of Elections to qualify for the ballot on Monday, October 27. Bailey’s political platform emphasizes conservative positions, including strong opposition to abortion, robust support for gun rights and law enforcement, and criticism of criminal justice reforms.
The investigation into the helicopter crash remains ongoing, with federal authorities working to determine the cause of the accident that claimed four lives in a single devastating moment.
