For more than three decades, Roy Gentry’s spent his free time in one sports arena or another. 

In the spring, he’s on the baseball diamond.

In the fall, it’s the gridiron.

During the winter, he’s in the gym on the basketball court.

Every night after working at the Blue Grass Army Depot, he comes home, changes clothes and heads out for practice or a game. Dinner’s usually around 8:30 or so, leaving a little time for wife Alma and ESPN before bed. 

For 10 months out of the year, that’s Gentry’s life. And he absolutely loves it.

“I played Little League baseball,” he said. “Two years after Little League started in Winchester, I started playing. The old Harmon Field is where we played.”

Though he loves them all, baseball remains his favorite. 

“The weather is good,” he said. “It’s a long period before you start coaching 9-10 year olds by the time you get them the high school ball. It’s a good feeling to see them come up and grow.

“It keeps me busy. It keeps me young.”

Gentry said he was recruited to coach Little League in 1986. By that point, he’d already been coaching Civitan basketball for five years and youth football for seven. 

That doesn’t even include the softball he plays as a competitor, just for fun.

“I love sports,” he said. 

The schedule would keep anyone hopping, and likely hoping for a break. Gentry said everything stops for a couple months after baseball ends in June. That’s when he does his fishing or takes a vacation with his family or visits his grandchildren. 

During the seasons, practices are crucial, he said, and even a missed day makes a difference.

“It makes me disappointed on a day like today when it’s raining,” Gentry said Friday. “They’ll forget something.”

While the skills may fade over time, Gentry said he still runs into former players frequently.

“I have coached guys that are still in Winchester and I’ve coached their kids and their kids. I’ve coached three generations. It’s unreal how many there are.”

There have also been a lot of championships for Gentry’s teams, which he estimates at 40, 20 came with the Civitan Cowboys in football. Another dozen came in Civitan basketball where he coaches the Celtics. In Little League, his A’s picked up about eight titles, he said.

“If they’ll give me an effort, I can teach them the fundamentals of three sports,” Gentry said, “and send them up a higher level. I like to win. I think losing is a bad word. I say we can win a ball game or another team can beat us.”

Though interest in the programs has slowed through the years, Gentry says all three programs are still vital and important.

“I think it’s real good,” he said. “Is it like it was 10 or 20 years ago? No, but it’s still good. The facilities are great. The kids still participate and the parents too.

“It’s not like it was, but it’s still there and it’a big function in this town.”

As long as the programs remain, Gentry plans on coaching.

“I wouldn’t give it up for anything,” he said. “I hope I can coach a bunch more years, as long as I have my health.”