On a Wednesday evening in late October 2025, the political noise in Illinois went silent. It wasn’t because of a debate or a poll. It was because of a tragedy in the Big Sky country of Montana that nobody saw coming. Darren Bailey, the former state senator and current 2026 gubernatorial candidate, lost a massive part of his world in a single instant.
The Darren Bailey helicopter crash wasn't just a news headline about a politician; it was the story of a family being torn apart.
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The details are heavy. On October 22, 2025, a Robinson R66 helicopter went down near Ekalaka, Montana. Onboard were four members of the Bailey family: Darren's son Zachary, his daughter-in-law Kelsey, and two of their children, 12-year-old Vada Rose and 7-year-old Samuel.
They didn't survive.
The news hit Illinois like a physical weight the next morning. You’ve probably seen the campaign photos of the Baileys—they lean heavily into that "faith and family" brand from their home in Xenia. But this wasn't a campaign strategy. This was a father and mother receiving a phone call that honestly changes a person's DNA.
The Timeline of the Montana Tragedy
The group was in Montana for what was described as a business trip. Zachary Bailey, who was 37 and a skilled pilot, used the family's helicopters for their massive farm operations back in Southern Illinois. He also frequently flew his father to campaign stops.
Basically, the helicopter was a tool of their trade.
Around 7:22 p.m., emergency services in Carter County responded to a crash site southwest of Ekalaka. This is remote country. We're talking about the Chalk Butte area—hilly, rugged, and not exactly the kind of place you want to have engine trouble.
By the time the sun came up on Thursday, the National Transportation Safety Board (NTSB) was already on the ground.
One detail that still haunts people is the story of Finnley. He’s the couple's 10-year-old son. He wasn't on that helicopter. Because the Robinson R66 only seats five and there were business partners and equipment involved, Finnley actually drove to the destination with a family partner. It was a literal twist of fate that spared him.
What the NTSB Investigation Reveals So Far
Whenever a high-profile crash happens, everyone wants answers immediately. But the NTSB doesn't work that way. They are slow. Methodical. Sometimes frustratingly so.
A preliminary report mentioned something significant: a witness reportedly saw a "component separate" from the helicopter before it plummeted. If you know anything about aviation, that's a terrifying phrase. It suggests a mechanical failure rather than pilot error, though nothing is official yet.
The helicopter involved was a Robinson R66. These are common turbine-powered choppers, but they have a history that investigators are likely scrubbing through right now.
Why the location mattered
Montana’s weather and terrain are famously unpredictable. While the crash happened in the early evening, investigators are looking at everything from wind shear to mechanical fatigue.
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The family's legal team, led by McNabola & Associates in Chicago, has already started their own deep dive. They aren't just looking at the pilot's logs; they’re looking at the manufacturer and maintenance records.
A Campaign Frozen in Time
For a few weeks, politics in Illinois just... stopped. Darren Bailey’s running mate, Aaron Del Mar, was incredibly blunt about it. He told reporters he "didn't care" about the campaign anymore. He just cared about his friend.
Even Governor JB Pritzker, Bailey’s fierce political rival, was visibly shaken during a press conference. He talked about his own experience losing parents young. It was one of those rare moments where the "red vs. blue" wall in Illinois actually crumbled for a second.
Then came the question: Would Bailey stay in the race?
Honestly, most people thought he was done. How do you stand on a stage and talk about tax policy after burying your son and grandkids?
But on November 10, 2025, Bailey released a video. He was standing with his wife, Cindy. He looked tired—who wouldn't be?—but he announced he was staying in the 2026 race. He said it was what Zachary would have wanted. He mentioned a phone call from Donald Trump encouraging him to "keep fighting."
Common Misconceptions About the Crash
There is always rumors. When a politician is involved, the internet gets weird.
- "It was a campaign flight." Not exactly. While Zachary did fly for the campaign, this specific trip to Montana was tied to the family's agricultural business and a convention.
- "The pilot was inexperienced." Zachary Bailey was widely known as a capable, licensed pilot who used aviation daily for the family’s fourth-generation farm.
- "Weather was the only factor." While Montana is rugged, the witness report of a "separating component" points toward a potential mechanical issue.
Moving Forward: What Happens Next?
If you’re following this story, you need to keep an eye on the NTSB’s public docket. These investigations usually take 12 to 24 months to reach a "probable cause" conclusion.
The Bailey family has been very open about their mourning process, often citing their evangelical faith as their primary support. They’ve even held "Celebration of Life" services that were packed with people from across the political spectrum.
For the rest of us, it’s a reminder of how fragile these logistics are. Aviation safety, particularly with light helicopters, remains a point of intense scrutiny in the U.S.
If you want to stay updated on the legal side or the NTSB findings, here is what to watch for:
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- The Factual Report: Usually released 6–12 months after the incident. It contains the raw data without the "cause."
- The Probable Cause Finding: This is the final word from the NTSB.
- Aviation Safety Advocacy: There is already talk in Springfield about tighter regulations for private agricultural aviation, though Bailey himself hasn't pushed for this yet.
The Darren Bailey helicopter crash will likely cast a long shadow over the 2026 election. Whether you agree with his politics or not, the tragedy of losing three generations in a single Montana field is something that resonates far beyond the ballot box.
Keep an eye on the NTSB's monthly aviation accident synopses for the next technical update on the Robinson R66's performance data from that night.
To help the surviving family members or stay informed on the investigation's progress, you can follow the official NTSB Montana aviation logs or look for updates from the Bailey family's community outreach programs in Xenia.