It was a Friday afternoon in September. Most country music fans were gearing up for the weekend, maybe looking forward to seeing Montgomery Gentry play at the Flying W Airport and Resort in Medford, New Jersey. Then the news broke. It didn't seem real. Troy Gentry, the guy with the wide grin and the signature black cowboy hat, was gone. The death of Troy Gentry on September 8, 2017, wasn't just another tragic celebrity headline; it was a freak accident that ripped the heart out of the country music community and left his duo partner, Eddie Montgomery, to carry on a legacy that was always meant for two.
People still talk about it. They wonder if it could have been avoided. When you look at the NTSB reports and the witness accounts, it’s a heavy story about a split-second decision and a mechanical failure that turned a "pleasure flight" into a nightmare.
The Moments Leading Up to the Crash
Troy loved to fly. He wasn't a pilot himself, but he enjoyed being up there. Before the show that night, he decided to take a quick spin in a Schweizer 269C1 helicopter. It was supposed to be a fun way to see the area before taking the stage. He hopped into the cockpit with James Evan Robinson, a commercial pilot. They took off, and for a few minutes, everything was fine.
But things went south fast.
About 75 feet in the air, the pilot started reporting trouble. Specifically, he couldn't control the engine rpm. This is a terrifying spot for any pilot to be in. If you're too low, you don't have time to react. If you're too high, you have a long way to fall. They were in that "dead man's curve" altitude where options are slim.
What the NTSB Investigation Actually Found
There's been a lot of rumors over the years. Some folks thought it was pilot error, others blamed the weather. The National Transportation Safety Board (NTSB) spent a long time digging through the wreckage. They eventually released a report that's pretty chilling to read if you've ever spent time around aircraft.
Basically, the mechanical failure started with the engine throttle cable.
The pilot tried to perform an autorotation. For those who aren't aviation geeks, that’s basically trying to land a helicopter without engine power by using the air moving up through the rotors to keep them spinning. It's a standard emergency procedure. But here’s the kicker: the NTSB found that the pilot chose to shut down the engine and enter the autorotation too early.
The report mentioned that the pilot's "failure to maintain rotor rpm" was a huge factor. Because the rotors slowed down too much, the helicopter didn't have the lift it needed to settle softly. It just dropped. It fell into a wooded area near the end of the runway.
A Scene Nobody Wanted to Witness
Eddie Montgomery was at the airport. He was waiting for his partner. He actually saw the whole thing happen, or at least the immediate aftermath. Can you imagine that? You've spent decades traveling the world, sharing buses, stages, and whiskey with your best friend, and then you watch his life end in a clump of trees just yards away from the stage you're supposed to play on together.
Emergency crews rushed to the scene. It took them nearly an hour to get Troy out of the wreckage. He was still alive when they pulled him out, which is almost harder to hear. He was transported to Virtua Marlton Hospital, but he was pronounced dead shortly after arrival. He was only 50 years old.
The Legacy of Montgomery Gentry
You can't talk about the death of Troy Gentry without talking about what the duo meant to country music. They weren't the "polished" Nashville types. They were the "My Town" guys. They represented the blue-collar, rowdy, southern rock side of the genre.
- They had five Number 1 hits.
- They won the CMA Vocal Duo of the Year in 2000, breaking a long winning streak by Brooks & Dunn.
- They were inducted into the Grand Ole Opry in 2009.
When Troy died, he left behind his wife, Angie, and two daughters, Taylor and Kaylee. The loss was massive. The funeral was held at the Grand Ole Opry House—a fitting place for a man who considered that stage his home.
Why This Tragedy Still Resonates
Honestly, it’s because it felt so random. This wasn't a long illness or a lifestyle-related tragedy. It was a guy having fun on a Friday afternoon. It reminds everyone that life is fragile. In the years following, Eddie Montgomery eventually went back on the road. He released a solo album. He keeps the Montgomery Gentry name alive, but he always leaves a spotlight empty for Troy.
There's a lot of nuance in how the industry handled it too. You saw a massive outpouring of support from guys like Blake Shelton, Kenny Chesney, and Brad Paisley. It showed that despite the "tough guy" image Montgomery Gentry projected, they were deeply loved within the Nashville circle.
Misconceptions About the Accident
One thing people get wrong is thinking the helicopter just "exploded." It didn't. It was a controlled descent that went wrong because of a lack of rotor speed. Another misconception is that Troy was piloting. He wasn't. He was a passenger. He trusted the professional in the seat next to him, and unfortunately, a series of mechanical issues and high-pressure decisions led to a fatal outcome.
The pilot, James Evan Robinson, also passed away in the crash. It was a double tragedy that left two families devastated.
Actionable Insights for Fans and Historians
If you’re looking to honor Troy's memory or understand the impact of his career, there are a few things you can do beyond just reading the headlines.
1. Listen to the "Here's To You" Album
This was the album the duo had just finished before Troy died. It was released posthumously in 2018. Hearing Troy’s voice on tracks like "Better Me" is incredibly poignant. It sounds like a man who was finding peace with himself before he passed.
2. Support the Troy Gentry Foundation
After his death, his wife Angie launched the Troy Gentry Foundation. It focuses on cancer research (Angie is a breast cancer survivor), helping military families, and providing music education. It’s a way to turn a senseless tragedy into something that actually helps people.
3. Watch the Grand Ole Opry Induction
If you want to see Troy at his peak, go back and watch the footage of their Opry induction. The joy on his face is infectious. It’s a reminder that he lived a life full of achievement, even if it was cut short.
4. Understand Aviation Safety
For those who fly private or do "experience" flights, the NTSB report on this crash is a sobering reminder to check maintenance logs and understand the risks of low-altitude maneuvers. Safety is never a guarantee, even in clear weather.
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The death of Troy Gentry changed the landscape of 2000s country music forever. We lost a voice that balanced out the grit of Eddie Montgomery with a smooth, melodic tone that made their harmonies iconic. It’s been years now, but the music hasn't faded. You still hear "Something to Be Proud Of" blasting out of truck windows every summer. That’s the real way to remember him—not by the wreckage in Medford, but by the songs that made a whole generation of country fans feel like someone finally understood their lives.