Troy Gentry Earned His First Tour Jacket — and Then, He Gave It Away

On Wednesday night (Feb. 5), Tracy Lawrence, Justin Moore, Terri Clark and more country stars gathered at the Grand Ole Opry House in Nashville to remember their friend and fellow artist Troy Gentry, who died in a helicopter crash in September of 2017. Both onstage during the second annual C'Ya on the Flipside benefit concert and backstage before the show, Gentry's kind heart, loving personality and hit-filled country music career were honored through stories and songs, all in the name of a good cause.

Perhaps the evening's most touching story, however, came from Gentry's widow Angie, who shared a tale from early on in her husband's career. "He was a really good guy with a really big heart," Angie told The Boot of her husband. "He had a lot of friends. He didn't know a stranger, and he was willing to stick his neck out for others. He'd give you the shirt off his back" -- in at least one case, literally.

Years ago, Angie recalls, Gentry and his Montgomery Gentry partner Eddie Montgomery earned their first tour jackets -- "a big, leather tour jacket from [Montgomery Gentry's record label], Sony," she shares, commemorating one of their first headlining treks. Gentry was wearing the jacket, which he "had just gotten," according to Angie, in downtown Nashville, when he walked past a homeless man without a coat.

"It was cold, and [Troy] walked by and he couldn't stand it, so he turns around and takes his first tour jacket that he ever got in Nashville and gives it to a homeless guy," Angie recounts. She wasn't with him at the time, but when Gentry explained where the jacket had gone later, he was focused on the homeless man's need for a coat rather than the jacket's sentimental value.

"He's like, 'The guy's cold and I have a coat, and I can get another coat and that guy didn't have a coat,'" Angie explains simply. In fact, Gentry was often giving to those less fortunate.

"Anything he could do to help somebody he was more than willing," Angie reflects. "You know the guys who sit at the end of the interstate and wash the windows and beg for spare change? Any time he was in the car, whatever he had on him, he rolled the window down and he'd hand it to them. He was like, 'I'm not sure what they're doing with it, but they need it more than I do.'"

In the wake of her husband's death, Angie -- who chose to donate Gentry's bones, tissue and corneas when he died -- founded the Troy Gentry Foundation in his memory, making that giving spirit part of Gentry's legacy. The organization offers financial support to cancer research organizations, groups that assist military families and organizations that focus on music education; Wednesday night's concert benefited the TJ Martell Foundation, Make-a-Wish, the Journey Home Project, Vanderbilt Ingram Cancer Center, St. Jude Children’s Research Hospital and music education initiatives in Gentry's home state of Kentucky.

Backstage at the Opry House, a little more than two years after Gentry died, Angie admitted that she was dealing with "a barrage of feelings" seeing all of the people who showed up to support the Troy Gentry Foundation and honor her husband. "It is overwhelming, it's very humbling, and it also warms your heart to know that the person you loved has affected that many people," she says.

"I think about him and what he would think if he were here," Angie shares, "and I think he would just be flabbergasted at all the friends and people that have come to show up and support the organization with his name on it.

"He was just -- he was a good guy," she adds. "I'm a little prejudiced, but he was a really good guy."

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