ANNA MARIA ISLAND – Charles “Chuck” Lester’s legacy of philanthropy and friendship is being remembered on Anna Maria Island following his passing on April 19 at the age of 92.
“I have nothing but great feelings for Chuck. I have such admiration and respect for a life well-lived,” Island businessman Ed Chiles said. “It’s a life and legacy that needs to be celebrated, not mourned.”
Lester passed away at HCA Florida Blake Hospital.
Holmes Beach resident Chuck and his wife, Joann “Joey” Lester, led philanthropic efforts, particularly for The Center of Anna Maria Island.
“He was half of the most wonderful couple in my history of being in business on Anna Maria Island,” Chiles said. “Joey was the love of his life; you never saw one without the other.”
Christopher Culhane, executive director of The Center, wrote in an email to The Sun:
“For almost 50 years, Chuck Lester touched the lives of many Anna Maria Island residents. The Center of Anna Maria Island will greatly miss Chuck Lester’s jovial and smiling face at this year’s upcoming 22nd Annual Lester Family Fun Day,” he wrote. “The Center and the Island community will be forever grateful for the lifetime support of Chuck and Joey Lester.”
Culhane wrote that the couple created an unparalleled legacy of giving both on Anna Maria Island and in Wisconsin.
“Their legacy will live on forever at The Center through the AMICC Endowment Fund, which was established through the generous support of Chuck and Joey Lester’s unrivaled philanthropy.”
Pierrette Kelly, executive director of The Center from 1989 through 2012, said Chuck started the Giving Challenge on the Island.
“He was a wise man. He said if you put a challenge out there, people will step up,” Kelly said. “They leveraged us to go outside our comfort zones to do more for the community.”
The Giving Challenge ended in November each year and the annual Lester Family Fun Day followed in December, bringing the community together to celebrate the holidays, philanthropy, kindness and generosity, Kelly said.
The free community event hosted by the Lesters at The Center included such activities as pony rides, games, food, crafts, a helicopter golf ball drop and a visit from Santa Claus.
Staff at Duffy’s Tavern in Holmes Beach took part in the Lester Family Fun Days.
“It was great to be a part of that. He gave so much back to the community and that’s what it’s all about,” Duffy’s owner Peggi Davenport said. “They were the sweetest couple. He will be greatly missed.”
Along with supporting charitable organizations he supported local businesses, Chiles said.
“He was a cheerleader for a lot of us, through good times and bad,” said Chiles, the owner of the Beach House, Mar Vista and Sandbar restaurants. “He was someone you could go to for advice.”
“They went north to their home in Wisconsin in the summers, but the Island always felt their presence,” Chiles said. “They didn’t just come here and take and drink from the bounty, they gave so much back.”
Chiles said Chuck Lester was known for his contagious laugh and easy-going manner.
“Everybody loved Chuck,” said John Horne, longtime friend of the Lesters. “He always had a smile on his face, you just wanted to be around him.”
“They touched so many lives. What a huge loss for our community,” Horne said. “My heart goes out to Joey right now.”
Horne, the owner of Anna Maria Oyster Bar, had served on the board of The Center of Anna Maria Island.
“For many years they were so instrumental in the community center,” Horne said. “They did more than just write a check, although they wrote many of those, but they put their lives behind their commitments.”
Horne said education and literacy was important to the Lesters and the couple started libraries in Wisconsin.
“He knew the ripple effect of supporting young children and literacy,” longtime friend of the Lesters, Darcie Duncan, said. “They started four libraries in Wisconsin. All of the things they did were done silently. They were passionate about what they supported.”
Duncan has known the couple for more than 40 years.
“Chuck always brought the room to life. Everyone wanted to be with Lesters,” she said.
Over the years, Lester gave Duncan advice for her real estate business.
“There are not many Chuck Lesters left,” Duncan said. “He was a gift.”
