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O.B. Osceola Sr. retires after a lifetime building chickees

NAPLES — O.B. Osceola Sr. got his start in the chickee building business when, as an 8-year-old, he

O.B. Osceola Jr, O.B. Osceola III, James Poole, O.B. Osceola Sr. and Dwight Cypress pose under the newly completed chickee at The Cove Inn in Naples on Feb. 22. (Courtesy of Tina Osceola)

handed his father Cory Osceola palm fronds that would be used for a new chickee’s roof. He loved the work but wanted to be on the roof building it with his brothers.

Eventually, Osceola, who grew up in Ochopee and the Everglades, started a chickee building business of his own in Naples.

After rebuilding one last chickee in February, Osceola, 84, has finally retired.

“My shoulders are kind of worn out,” Osceola said. “All the young guys can build them now. I’m retiring but if the right job comes along, I’ll do it.”

The chickee bar at The Cove Inn in Naples was destroyed during Hurricane Irma when the hotel’s roof blew off and landed right on top of it. Osceola originally built the 25-by-18-foot chickee in 1969, but the hotel decided to take the opportunity to rebuild and expand it to 46-by-25 feet.

The chickee, which took about a month to complete, was built brand new from the ground up and includes new pressure treated pine poles and 7,200 cabbage palm fronds collected from private land.

“It will stay for a lifetime now, if the hotel doesn’t fall on it,” Osceola said.

On the last day of Osceola’s last chickee, he used a crew that included his son O.B. Osceola Jr. and grandson O.B. Osceola III.

“Today I recommend people get an education and learn a trade,” Osceola said. “Chickees are a traditional thing and something to fall back on, but make sure to get an education.”

His children heeded his advice and earned college degrees. His son Osceola Jr. is a business owner and daughter Tina Osceola is an associate judge on the Tribal Court.

The chickee business was good for Osceola, who never received a higher education. After riding out Hurricane Donna in a camp in Ochopee, the Osceola family moved to Naples. Once there, they built chickees for some of its founding families including the Watkins, who developed the Naples Beach Hotel and Golf Club, and the Colliers, who developed large swaths of the county named for them.

After serving in the U.S. Army in the late 1950s, Osceola came home and went to work building chickees in Southwest Florida. He built a Seminole Village on U.S. 41 for the Collier Family Company.

“We were squatters and they treated the Seminoles well for many years,” he said. “We had a good relationship.”

After building another village in East Naples, in Osceola started building chickees full time and has been doing it ever since. His business went international when he was hired by a Caribbean resort in Bonaire to build two large chickees, one for a restaurant and the other for a bar.

The project took 22,000 palm fronds to build, which Osceola shipped in a container from Port Everglades. The success of those chickees led to other jobs in the nearby islands of Aruba and Curacao. In the 1960s he also built two chickees at the Colusa Indian Community’s casino near Sacramento, California.

A family man, Osceola sells arts and crafts with his daughter Tina at events and on dividend day in Hollywood. He also collects and repairs antique sewing machines. Osceola, who never smoked or used alcohol, said his doctor recently told him he has the “insides of a 65- year-old.”

“I have no complaints,” Osceola said. “I have lived a good life and wouldn’t change anything.”

Beverly Bidney
Beverly Bidney has been a reporter and photographer for The Seminole Tribune since 2012. During her career, she has worked at various newspapers around the country including the Muskogee Phoenix in Oklahoma, Miami Herald, Associated Press, USA Today and other publications nationwide. A NAJA award winning journalist, she has covered just about everything over the years and is an advocate for a strong press. Contact her at

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