Four family members of Illinois Republican gubernatorial candidate Darren Bailey were killed when their helicopter crashed in southeastern Montana on Wednesday, October 22, 2025.
Bailey’s son Zachary, who was piloting the aircraft, died alongside his wife Kelsey and two of their three children—12-year-old Vada Rose and seven-year-old Samuel. The couple’s 10-year-old son, Finn, was not aboard the helicopter at the time of the crash. The family’s aircraft went down near Ekalaka, Montana, with emergency services responding to the scene at 7:22 p.m. Wednesday.
According to Capitol News Illinois, “Darren and Cindy are heartbroken by this unimaginable loss. They are finding comfort in their faith, their family, and the prayers of so many who love and care for them.”
The Bailey campaign announced the deaths early Thursday morning in a statement requesting privacy for the family during this difficult time. The campaign emphasized that Darren Bailey and his wife Cindy appreciate the outpouring of support they have received as they grieve with their remaining family members.
The National Transportation Safety Board confirmed Thursday morning that it is investigating the crash of a Robinson Helicopter R66 in the southeast part of Montana. Details about what caused the accident have not yet been released by authorities, and the circumstances surrounding the crash remain unclear.
Zachary Bailey regularly piloted helicopters for both the family’s farming operation and campaign events, according to local news reports. The Bailey family operates a fourth-generation farm in southern Illinois, where Zachary worked alongside his father and brothers Cole and Mason. The farm’s operations have been central to the family’s identity, with Zachary playing a key role in managing the agricultural business that has been passed down through generations.
Darren Bailey, 59, is currently mounting his second campaign for Illinois governor, having previously lost to Democratic incumbent JB Pritzker in the 2022 gubernatorial race. That election became one of the most expensive non-presidential races in American history, with both sides pouring tens of millions of dollars into the contest. Bailey secured the Republican nomination but lost by a wide margin in the general election. He received Donald Trump’s endorsement after appearing at a campaign rally with Trump in June 2022.
The southern Illinois politician previously served in both houses of the state legislature, representing parts of southern Illinois. His 2026 campaign is being run alongside Cook County Republican Party Chair Aaron Del Mar as his running mate. Bailey has positioned himself as a conservative candidate strongly opposed to abortion, supportive of gun rights and law enforcement, and critical of criminal justice reforms.
Bailey and his wife Cindy have four children and 13 grandchildren total, with family members featured prominently in his campaign materials. The couple’s large family has been central to Bailey’s political identity as a grain farmer and family man from rural Illinois.
Governor Pritzker expressed his condolences at a news conference in Chicago on Thursday, becoming emotional as he reflected on his own experience of losing his parents at a young age. The governor indicated he could not imagine the pain of losing a child and two grandchildren, stating that he and his wife were devastated by the news. Pritzker added that his prayers and deep condolences were with the Baileys during this time of grief, expressing hope that memories of their loved ones would be a blessing.
Other political figures across party lines also offered their sympathies. Ted Dabrowski, one of Bailey’s Republican opponents in the 2026 gubernatorial race, released a statement indicating that he and others grieve with Darren and Cindy Bailey. Dabrowski noted that the family’s deep faith and strong family ties would support them through this difficult period.
The tragedy comes at a significant moment in Illinois’ political calendar. Bailey and other candidates for office in 2026 were scheduled to begin turning in petitions to the State Board of Elections to qualify for the ballot on Monday, October 27.
The investigation by the National Transportation Safety Board is ongoing, with officials expected to release more information about the crash as their examination of the incident continues. The agency has not disclosed a timeline for when findings might be available regarding what led to the fatal accident.