Hard-working ‘wanderer’

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Flagpole painter chose his profession at 15

By Alice Du Pont

Harold Usry doesn’t really have a place to call home. Now 56, the entire state of Florida, from Escambia County (Pensacola) to Monroe County (Key West) is where he lives.


Usry has a most unusual occupation: He paints flagpoles. That’s how he makes his living, going from town to town, just painting flagpoles. His meager belongings are never too far away from him, usually tied to his Huffy mountain bike that he lovingly refers to “the old lady.” 

“The old lady” brought him to Gadsden County on Aug. 1. While she rested, leaning against the railing on Courthouse Square, Usry, in a paint-splattered, tattered, sleeveless red T-shirt, scampered up the flagpole on the south lawn of the courthouse to assess the job at hand. He needed to know what would be needed to shine the 

rusting pole.

First, a few limbs that had grown over part of the pole since Usry last painted it sux years ago had to be trimmed away. That task done, the next step was to scrape down the pole to remove chipped paint and rust.

A second-generation flagpole painter, Usry said he learned the job as a child from a beloved uncle and launched his own career at 15 years old.

“I figure I have painted 10,000 or more flagpoles in the state of Florida. My work includes everything — the paint and the manpower. I try to get all of the poles I can while I’m in a place,” he said.

He initially made contact with Clyde Collins, facilities manager for the county, about painting the pole on the square.

“He said he came here about four or five years ago and said he had painted the flagpole. He knew Freddie (McNealy), so I put him to work,” Collins said. 

In addition to the courthouse, Usry painted county owned poles at the records center, the jail and the emergency room. McNealy said he was glad he came because the pole at the emergency room needed a new rope and Usry replaced it. 

Wayne Shepard, facilities director for the school district, said he met Usry about 15 years ago when he came through town.

“He’s a great guy. I call him a wanderer. He wandered through here years ago and I met him. He told me he painted flagpoles so he got to work. I was pleased with his work, and when he come back through he painted them for us,” Shepard said. 

Usry doesn’t get rich painting flag poles. Has standard fee of $225 includes the paint and labor. To remove a few limbs is thrown in free. He can scrape down and paint a pole in about 90 minutes. The work can be extremely hot or extremely cold but he, a free spirit, makes his own hours.

He had just painted all of the flag poles in the Central Florida town of Zephyrhills and he’ll be finished with Gadsden County in a few days.

“Me and ‘the old lady’ will gather up the paint and rope and hit the road again,” Usry said.