Chester Rogers – A Fort Myers Beach Icon


(By Kim Ryan) Fort Myers Beach is filled with interesting characters and Chester Rogers certainly fits into that category. You can’t miss Chester while traveling along Estero Boulevard. The local and beloved artist, with all of his drawings, paintings and supplies, has a prime location, right under a shade throwing Black Olive tree in front of The Surf Club. On July 5th, Chester celebrated his 10th anniversary in that very spot. In all, he’s been drawing and painting for residents and tourists for about 20 years.

Chester Rogers was born in 1951 at Lee Memorial Hospital here in Lee County. He started painting on the beach back in the 1980’s. Then, he went off and did the family thing before returning to the beach in 2007 once his three kids were out of school.

During the day, every day, Chester sits under “his” tree and he paints and draws. He really enjoys painting for the kids. He loves to put a smile on their faces. He works for tips and he refuses to take any money for anything he does for kids.

Chester Rogers

At night Chester goes home and he paints. He works in all the mediums; oil, watercolor, pastels, acrylics. Gougan is Chester’s favorite artist. His most popular pieces are of the view coming over the sky bridge, Times Square and Shrimp Boats. He also has cards and envelopes. And he told me it’s all started selling lately. “I have people walk by telling me I’m getting better with age.” Chester is 69.

When I spoke to Chester in July, cars were rolling by beeping their horns at him yelling hello. He jokingly commented, “They all know me.” Actually, it isn’t a joke. It’s true. Everyone does know Chester.

Believe it or not, Chester has never taken an art class in his life. “I was getting ready to start Edison Park elementary when I was 5 years old. My brother and I were using our new school supplies drawing on the wall in our house. My mom was the kind of person who would spank you in a heartbeat, so when she left the room my brothers were hollering to get a towel quick to clean it up. She came back with a frame for my picture. I have been drawing ever since.”

Today, Chester lives on the beach and collects $750 a month in disability. He says other than that, the beach people take care of him. And, he says he has a really nice studio under that Black Olive tree.

Earlier this year, Chester was suddenly out of supplies when someone stole all of his stuff and threw it all into the canal. Just like that he was out of business. But not for long. Want to know just how much islanders love Chester? The people of Fort Myers Beach came to his rescue. “The island people helped me with so much new stuff, I had to put a note on Facebook twice that they had done enough. They care for me.” He was back drawing and painting 24 hours later.

And Chester pays it right back. “I  do events for kids with Autism or Down’s Syndrome, church events. I’m ready with my supplies and I can maintain safety (with masks, sanitizer and 6 ft distance). Its all free for them. Please, it makes my day.”

Chster paints for the people.

Chester is one of the most cheerful people you’ll ever meet. Friends come by the chat with him and exchange old stories. One of the stories Chester shared with me had to do with a challenging time in his life that he had to overcome. “I had a tough 7 months during my life when one of my kids had to have his rib cage removed. Then, my wife found a new guy, I had 6 strokes and I was no longer an overachiever. I lost my Century 21 franchise and I was hit by a car.” Chester wound up homeless for over two years. But, it didn’t break him. He says God delivers miracles because today he says he’s happier than he’s ever been in his life.

Chester doesn’t have a website to promote his art but he is a very avid Facebook user and you’ll see him post some of his work on the social media platform for all to see. He does take requests but wants everyone to know, “I don’t do politics or pornography so don’t bother me with any of that.”

It’s just a guestimate but together with Chester we calculated that he’s drawn and painted over 12,000 pieces while sitting under that Black Olive tree over the past ten years. 90% of those were given away for free.

Kim Ryan is the President of Beach Talk Radio News and can be reached by e-mail at


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