A Man for All Seasons

In Dawson Springs, Kentucky—a town that barely dots the map and where everyone knows your name—Jeff Winfrey found his crucible at the epicenter of calamity, not once but twice. First came the tornado of December 2021, a monstrous beast that ripped through half the town like an unkindness of ravens. 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 you'd peg as a community leader. A retired dentist and pastor of a small Primitive Baptist Church, he was content with the quiet rhythms of small-town life. "I'm a nobody from a nowhere place," he’ll tell you, shrugging off any notion of grandeur. But disasters have a way of drafting unlikely soldiers, and Jeff was conscripted by circumstance.

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

"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." 

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 explained. "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 plunged into the labyrinth of committees, board meetings, and strategy sessions. He teamed up with Habitat for Humanity, Catholic Charities, and any outfit willing to roll up their sleeves. "We worked together well," he said of these 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 recounted standing amid the wreckage of obliterated homes, fearing the worst for friends and neighbors. "I just stood there and wept," he said. "Those kind of memories just... I'll never lose that."

Public opinion is a fickle beast, and Jeff knew it all too well. "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. He knew he couldn't please everyone, but that was never the mission. The mission was to keep moving, to keep helping, even when the road was littered with potholes and second-guessing.

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 stack of bills became more than just money; it was a lifeline, a glimmer of hope amid the rubble.

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 nature's fury and witnessed the darker angels of human nature, yet he refuses to back down.

In the grand tapestry of small-town America, where stories like Jeff's often go untold, he stands as a testament to quiet resilience. He didn't ask to be the face of Dawson Springs, but when the role landed on his doorstep, he also 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 the day, Jeff's journey isn't about accolades or recognition. It's about doing the work that needs to be done, even when it's thankless, even when it's hard. And in that relentless commitment, he captures the essence of a town battered by storms but unbroken in spirit.