Report: Object detached from helicopter before crash that killed Illinois politician's son

BILLINGS, Mont. — A witness to the crash that killed Illinois politician Darren Bailey's son and family members said he saw something come off the helicopter before it wrecked, according to a federal report just released.

The Oct. 22 accident killed the pilot, Bailey's son Zachary Bailey, Zachary’s wife, Kelsey, and two of their three children.

Darren Bailey is running for Illinois governor, and has been urged to stay in the race by President Donald Trump. That race will be on the November 2026 ballot; Bailey is a Republican and the incumbent, JB Pritzker, is a Democrat.

The new report, from the National Transportation Safety Board, said a friend of Zachary Bailey’s reported the helicopter, a Robinson Helicopter Co. R66, departed at 6:18 p.m. at dusk alongside a Cessna 182, a four-seat airplane, from a ranch near Ekalaka, in rural eastern Montana.

The family was in Montana as part of the farming business Zachary helped his father run, the Associated Press said.

Instead of going directly to Ekalaka’s airport, Zachary Bailey decided to fly over the Chalk Buttes, a small mountain range, on the way to the town with a population of 400. The friend piloting the plane said the helicopter pilot flew around a set of buttes. The helicopter then flew through a gap in the rocks and made a right turn toward the plane.

Zachary Bailey trailed the plane by about a half-mile to a mile, the plane's pilot said.

According to the report, it was the last time the plane saw the helicopter. One minute later, the plane’s pilot did not see the helicopter’s flight being tracked, and was unable to establish radio contact with Zachary or his family, despite multiple attempts.

According to an unnamed witness in the preliminary report, she was inside her house when she heard the helicopter and went to a nearby window to look.

She said she saw the helicopter flying low over the buttes and believed the plane was trailing behind it — an observation that contradicts what the plane's pilot reported.  As the helicopter began to gain altitude, she said something came off of it before dropping out of sight.

The accident site showed the helicopter crashed in an open field next to the Chalk Buttes range. Debris was scattered over an area about 300 feet wide and 300 feet long. The wreckage has since been moved for further examination.

The incident is classified as a Class 3 investigation, meaning the ongoing investigation will seek to identify safety issues to reveal the cause or causes of the accident.

According to a NTSB report, the 2014-manufactured helicopter was involved in a past crash on Oct. 29, 2014 near Baton Rouge, Louisiana. The helicopter was owned by a Louisiana-based pilot training company at the time.

During that 2014 pilot-training flight, the helicopter encountered three birds at a relatively low elevation. A bird then impacted part of the helicopter's rotor disk, causing "substantial" damage to the helicopter with a dent at the leading edge of the rotor blade. The helicopter wasn't certified airworthy again until 2022, according to the Federal Aviation Administration's registry.

Robert Katz, a Texas-based commercial pilot with 44 years of experience flying planes, previously told the Billings Gazette the prior incident concerned him as it appears the helicopter sat idle for eight years between the date of the accident and its airworthiness certification

"Anything that sits idle is all the oil is going to drop to the bottom of the pan. Corrosion will develop, not only inside the cylinders, but also throughout the moving parts of the machinery," Katz told the Gazette previously.

He said all the moving parts of helicopters make them more maintenance-intensive than planes. Because of that, it can be easy for helicopter owners to neglect required maintenance, he said.

After seeing the preliminary report, Katz speculated that the wide spread of the crash site could indicate an in-flight failure.

“When you have wreckage spread out like that, it's because what's coming apart is up at altitude, and the momentum of the aircraft, plus wind is going to spread all that wreckage out over a wider area, versus an aircraft that comes down in one piece,” he said.

The NTSB report reaching a final conclusion around the circumstances and causes of the crash won't be available for more than a year. The preliminary report was released this week. 

Darren Bailey, the gubernatorial candidate, announced earlier this week on Instagram that he will stay in the race for Illinois’ governor, even after the crash involving his family. He said President Donald Trump had called him personally after the crash to tell him to “keep fighting” and to not back down in the race against Pritzker, a vocal opponent of the president. 

“After a lot of prayer and reflection, Cindy and I have decided we’re staying in this race for governor,” the Republican politician added. “Not for politics, but for every family trying to make it in a state that’s lost its way, for every parent who dreams of a better future for their children and for every Illinoisan who knows that we can do better."

It was the campaign’s first post on Instagram in roughly two weeks running up to the 2026 governor's race. Darren Baily appeared alongside his wife Cindy in their home in the three-minute video. 

“The last two weeks have been the hardest days of our lives, but your prayers, your messages and your love have carried us, and we are so grateful,” the gubernatorial candidate said.