A Man for All Seasons

In Dawson Springs, Kentucky, Jeff Winfrey met his crucible twice over when back-to-back tornadoes demolished his town.

First came the tornado of December 2021, that ripped through the town like a ravenous beast. Then, as if the universe hadn't had its fill, another tornado barreled in on a late May evening earlier this year, turning what was left into kindling debris and dust.

Jeff wasn't the guy from central casting chosen to be a community leader. Retired dentist and pastor of a small Primitive Baptist Church, he was content. "I'm a nobody from nowhere," he’ll tell you, shrugging off any notion of grandeur. But disaster drafts its own infantry, and Jeff got called up.

"The recovery is still ongoing," he told me in the small, neatly appointed office of his church. A church whose picture became the poster child for the horrendous tornado damage done, owing to the amount of destruction that had laid waste to its structure. A picture of the destroyed church played out on front pages of newspapers and in broadcasts across the nation. "It's still ongoing from the first one. We've still got a lot of people needing help that way." 

"I'm a nobody from nowhere," he’ll tell
you, shrugging off any notion of grandeur.

The first tornado had obliterated rental properties, displacing the town's most vulnerable—the elderly on fixed incomes, folks on disability scraping by on rice and beans, families who couldn't afford a mortgage even if you gift-wrapped a house for them. "People lost everything they had," Jeff said. "That group right there has been difficult to help."

And for the first time in anyone’s memory, Dawson Springs has a homeless population that lives in corners and the shadows that only a small town can manufacture.

Jeff saw the widening cracks in the system, the people slipping through like smoke into the gray. He became a reluctant linchpin in the town's rebuilding efforts, stepping up as the pastor of a modest church that suddenly found itself a magnet for out-of-state donations. "Money started pouring into this church," he said. "People were calling, and they wanted to help our town or help our church. They didn't want to give to big-name groups” because they were concerned the money would be siphoned off to pay organizational administrative costs, Jeff said. “I want my money to go help somebody,” was a refrain he heard time and time again.

With a mix of humility and a no-nonsense sense
of duty, Jeff took on the role of steward.

With a mix of humility and a no-nonsense sense of duty, Jeff took on the role of steward for these unexpected funds. "When I spend this money, I would think that you'd be happy if you were standing right beside me," he promised the donors. "And I know the Lord's standing beside me.” 

It was a learning process tempered by adversity. “I've blown it,” he says. “I've messed up sometimes. I've been conned."

But setbacks didn't slow him down. Jeff successfully navigated a sea of committees, board meetings, and strategy sessions. Habitat for Humanity, Catholic Charities, he teamed up any outfit willing to roll up their sleeves. "We worked together well," he said of such alliances. "And that was a good experience. Has been, still."

The weight on his shoulders was palpable. "You do carry a lot of weight sometimes it feels like," he said. "The load gets sort of heavy when you hear a lot of problems." He remembers standing in the wreckage, fearing the worst for friends and neighbors. "I just stood there and wept," he said. "Those kinds of memories just... I'll never lose that,” he said, his voice tailing off into a whisper.

Public opinion is fickle, and often caught the brunt of it. "People are people," he said. "You've got some that's got their hand out that don't need it, and you've got others that need more than what we've got." He faced his share of armchair critics and social media snipers. "I've had my name plastered on Facebook because I'm on these committees," he said. "You can do nothing, and nobody will ever say anything bad about you. You can try to do something and take the risk... then somebody else is mad at you 'cause you didn't build them [a house]."

"If we're going to err, let's err on the side of love."

Still, his guiding principle remains unshaken. "If we're going to err, let's err on the side of love," he says. Can’t please everyone, he knows that, it was never the mission anyway. The mission was to keep moving, even when the road was littered with potholes and second-guessers.

One Christmas morning, pockets stuffed with rolled-up hundred-dollar bills in $500 bundles from the donated cash, Jeff walked the ravaged streets. He approached a lifelong acquaintance who was sifting through the debris that used to be his home. "This isn't going to get back what you lost, but Merry Christmas," Jeff told him, handing over the money. "I had guys twice my size pick me up off the ground and tears just flowing off their face," he said. In that moment, a slim stack of bills became more than just money; it was raw hope. 

Jeff doesn't see himself as a hero—far from it. "I've been told, ‘you're not the pastor of this church; you're Dawson Springs' pastor,’" he said, almost sheepishly. "I'm saying that, and I feel real small by saying that because I'm not supposed to be bragging." He's acutely aware of his own imperfections and the limitations that come with being human. "You can't change them," he said about the naysayers and opportunists. 

He didn't ask to be the face of Dawson Springs, but when
the role landed on his doorstep, he also didn't flinch.

But he keeps at it. He shows up to every meeting, signs up for every committee that needs a hand, and visits every home where a comforting word might make a difference. He's stared down the barrel of fury and witnessed the darker angels of human nature, yet he refuses to back down.

And so it goes. Amid the tapestry of small-town America, Jeff’s example stands as testament to resilience. He didn't ask to be the face of Dawson Springs. When the role landed on his doorstep, he didn't flinch. By stepping up, he offers a blueprint of what can happen when a community chooses unity over division, action over apathy.

At the end of our time together, I slipped another $1,000 stack from my pocket and pushed it his way. His eyes grew wide. Speechless. “No strings attached,” I said, launching into my usual patter about giving back to those who seek nothing in return for all they do. He began to openly weep.

“This just keeps happening,” he said, wiping his eyes. “Are you an angel?” he said, straight up, no smile or joking implied. At first I thought of saying, “Well, I couldn’t tell you, even if I was,” but opted for the obvious truth. “No, no,” I said with a chuckle. “I’m far from it.” I asked what he thought he might do with the money.” 

At first he said he’d just give it back to me, a donation to help me keep going. I politely refused the gesture. “Well, there’s any number of folks who could use this,” he said. “I promise you this, I’ll multiply this money.” 

He folded the bundle into calloused palms—careful, almost fearful of bruising something tender and alive. Lips moving without sound, a silent prayer rolling beneath his breath. Then he lifted his gaze toward the shattered horizon—the same one that had twice tried to flatten his town—and I watched resolve rise behind his tear-rimmed eyes like dawn behind broken rafters. He shook his head, a slow, reverent motion, as though the possibilities were too wide to name. “Whatever it becomes,” he said finally, voice steadying, “it’ll be seed in good soil.”

We stepped outside. The late-afternoon light poured across the scarred streets. Somewhere a hammer struck, sharp and rhythmic as a choir of cicadas tuned up for evening. He tucked the money inside his worn leather Bible, pressed it shut, and laid a broad hand over the cover—part oath, part blessing.

“Stay the night,” he said. “I have a parking spot in front of my shed with your name on it.” A safe harbor. He also promised a shore power electrical connection I could plug into the side of Josie so I could use the 110v outlets I’d installed in her living space. I gratefully accepted.

In the morning he invited me in. His wife offered to cook up a good ol’ country breakfast; I opted for a bowl of cereal instead. 

“Thank you for believing in us,” he said.

I told him belief was easy. All a man had to do was stand on this cracked pavement and listen. The hard part, I said, was to drive away and leave that music behind. 

He laughed then, soft and grateful, and we clasped hands in the dust that had drifted in from Main Street—two travelers headed in different directions, carrying the same small flame. I climbed into Josie and eased her onto the road, the town receding in the mirror. Behind me, the pastor turned toward the rubble and the rising walls, pockets heavy with promise—and richer than ever for it.