November 1, 2023 | Stewardship
Fr. Stephen Van Lal Than

Charles “Charlie” Winstead delivering the mail as a young man. COURTESY OF WINSTEAD FAMILY

‘Quiet, faithful’ parishioner leaves legacy that will impact local Catholics for years to come


Charlie Winstead was a quiet, unassuming man who spent thousands of Masses in the back pew of St. Stephen Cathedral. He was an usher there for 54 years. In addition to being an Air Force veteran, he was also known for his many years of delivering mail for the U.S. Postal Service. Last month, Charlie quietly passed away at the age of 87. His pastor at the cathedral, Fr. John Thomas, described Charlie as a “quiet, faithful man. He tried never to bring attention to himself.” He often volunteered in the office, and regularly visited the Carmel Home to play cards with the residents.

But Charlie wasn’t just a quiet servant while he was alive. He left a legacy of significant generosity at his passing that will continue to powerfully serve the Catholic Church for many more years to come. For years, he would take out a charitable gift annuity (CGA) each year. The gift annuity provided him with a guaranteed income each year, a generous tax deduction, and now at Charlie’s passing, the dollars will support the work of the Catholic Church in his name for many more years to come. The beneficiaries of the fund he established now goes to St. Stephen Cathedral, Gasper River Catholic Youth Camp and Retreat Center, the Ursuline Sisters of Mount Saint Joseph and the Glenmary Home Missioners.

The first gift to the CGA was in 2008, and then annually for the next eight years he purchased another one.

“It’s been nearly five years since I sat with Mr. Winstead in his living room,” said Kevin Kauffeld, who was chancellor of the Diocese of Owensboro until 2019. “He loved old-time bluegrass music, and he played it on a stereo that looked like something right out of Antiques Roadshow! Seeing his obituary brought back a lot of memories of a friendship we developed over the years. He loved his cathedral parish family.

“I can see Mr. Winstead riding his bicycle through the streets of Owensboro on his way to a hot card game at the Carmel Home,” added Kauffeld. “He loved a game called ‘Pedro.’ He was a humble man. My life was enriched by the time I spent listening to bluegrass music with him.”

And the generosity of Charles Winstead will continue to enrich the work of the Catholic Church for many years to come.

To learn more, contact Valeria Vessels at (270) 683-1545 or email her at [email protected].

Originally printed in the November 2023 issue of The Western Kentucky Catholic.

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