ANNA MARIA ISLAND – The Island lost a dear friend with the recent passing of JoAnn “Joey” Lester.
On June 1, Joey passed away at the age of 97 in her hometown of Wisconsin Rapids, Wisconsin.
Joey’s husband, Chuck, passed away in 2024 at the age of 92. For several decades, the beloved couple split their time between their hometown in Wisconsin and their adopted second home on Anna Maria Island, where they owned a home in the Key Royale community in Holmes Beach.
Chuck was a banker and Joey’s family was in the paper mill business.
If you didn’t know them, but the name sounds familiar, you’ve probably attended Lester Family Fun Day at The Center of Anna Maria Island – the signature annual holiday event sponsored by the Lesters.
On June 2, Duncan Real Estate owner Darcie Duncan shared the following message on Facebook: “Heaven welcomed one of the most beautiful souls I’ve ever been blessed to know. Joey Lester, since I was a young girl, you were always my cheerleader – standing beside me through every up and down, loving me without fail.
“Because of you, I became a Packers fan, a lover of Wisconsin cheese (especially the aged cheddar) and a fixture at Badgers tailgate parties. So many of my favorite memories live on Nepco Lake, where the days felt endless and the laughter never stopped.
“The legacy you and Chuck built will resonate for generations. We are all forever grateful, and you will live in our hearts always. There’s really only one word for a life like hers: Supercalifragilisticexpialidocious.”
Sandy Pruett worked at The Center when the idea for Lester Family Fun Day first originated.
“I’ve had the great honor of knowing the Lesters since I began working at the Anna Maria Island Community Center in 1999. It was then that Chuck approached the director, Pierrette Kelly, with the idea for a holiday event centered around the theme: ‘Old-fashioned FUN at old-fashioned prices.’ That vision became Lester Family Fun Day,” Pruett said, via email.
“While Chuck and Joey underwrote the costs, I had the privilege of planning the event with him. He envisioned food, rides, prizes and Santa hearing the children’s wish lists – at one point, he even discussed bringing in an elephant! Over the last quarter of a century, this idea has grown into a beloved tradition for all ages – though we ultimately decided against the elephant. It is a joy to see adults who attended The Center as children now bringing their own families to this amazing event. They truly lit up whenever parents and children approached them to say, ‘Thank you.’ Joey and Chuck were a blessing to our community. What a gift it was to those whose path crossed theirs,” Pruett said.
“On a personal level, Mark and I became dear friends with the Lesters over the years. They were incredibly generous and thoughtful people. We had a standing ‘date’ with them on Sundays to watch their beloved Packers; or join them to toast a sunset on the Sandbar deck; or just stop by to say a quick ‘Hi,’ which lasted for hours. We will always cherish our time with them and the precious memories that are forged in our hearts forever,” Pruett said.
Jim Sykes and Gayle Lindquist collectively said, “Joey was the kindest and most generous person we’ve known. Not only were we visitors in Florida, we were lucky to stay with them in Wisconsin. We would show up and we were so welcomed. When we visited, Chuck and Joey were so fun to be around.”
THE CENTER
Chris Culhane has served as The Center’s executive director for the past seven or eight years and he’s worked at The Center for approximately 11 years. Marketing and Office Administrator Aris Thompson’s time at The Center dates back approximately 20 years.
“What an incredible legacy the Lesters both created for us here at The Center. They were always here for The Center and they created the endowment fund in the early 1990s,” Culhane said.
“The endowment is currently with the Manatee Community Foundation and we’ve built upon it over the years. We can take the interest yearly, if we choose to, or continue building the fund for the future, which is what we’ve done since I became the executive director – so this place is safe for years to come,” Culhane said.
Culhane said he met the Lesters when he took his children, who are now in college, to a Lester Family Fun Day – before his tenure at The Center began. He noted this year’s Lester Family Fun Day will mark the event’s 25th anniversary.
Thompson said, “Joey and Chuck wanted to have a fun day that anybody could come and enjoy, so they covered the costs of the food and entertainment. They wanted the kids to have fun. They were both kind, happy people and they were excited to see everybody else having fun and visiting with Santa. They just wanted to do good for the community.”
“They’d sit and watch the kids and have a Duffy’s burger and their smiles were infectious. They loved watching the kids,” Culhane said.
“Joey and Chuck made a monumental impact on The Center and the entire Island community. They were our largest benefactors and their support for The Center has helped this community grow for many years. Around five or six years ago, we dedicated one of the oak trees on The Center property in their honor. We call it ‘The Giving Tree,’” Culhane said.
“As people, they were joyous,” he added.
COMMUNITY SUPPORTERS
Former Sandbar, BeachHouse and Mar-Vista restaurant owner Ed Chiles has known the Lesters for more than 40 years.
“It was always Chuck and Joey and they were always together. They were just the nicest couple. They were the epitome of the best of people that are philanthropic and support their communities and the businesses and charities in those communities. I don’t know anybody who gave more than they did. Their support of The Center was known to everyone and they did that back in their hometown in Wisconsin too,” Chiles said.
“They also supported so many Island businesses and that support came with a relationship. When I first started out, they were always behind me – and Darcie and others will tell you the same thing. They had a ‘trap line’ that included so many of us. It was always great to see them. They were the couple you sat down with. They were always interested in what was going on. They’d impart a little of what they knew on you and you’d impart a little of what you knew on them. You were always so glad to see them and they were always so glad to see you. They were also great customers,” Chiles said.
“Joey liked her meat. Joey wasn’t a fish eater. Any time I had a new meat dish, I would show that off to Joey. They loved good wine and fine food and Wisconsin cheese. I remember one time they brought us some 50-year-aged Wisconsin cheddar. It was the best cheddar I ever had – it had crystals that almost had a little crunch,” Chiles said.
“During one of the last interactions I had with Chuck, he said he wanted to make a contribution to what we’re doing to protect our coastal waters and he wrote me a $10,000 check for the bivalve (oysters and clams) project,” Chiles said.
“Joey’s health declined a little bit during the last couple years, but what a great run they had; and you really have to celebrate a life well-lived. Every time I think of them, I will have a big smile on my face,” Chiles said.
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