This painting by Frank Sinatra is up for auction by Leslie Hindman Auctioneers. It was found in a Venice thrift store.

Former city employee Don Caillouette wasn’t looking for treasure 20 years ago when he entered a second-hand store while shopping in downtown Venice.

What caught his eye was a beat up old picture frame. In the frame was a Thanksgiving harvest theme oil painting. In the bottom corner it was signed “F. Sinatra 1955.”

The “F” probably stood for Francis or Florence, thought Caillouette. Surely not Frank Sinatra. But maybe …. For the price of $8.56 he took a chance and took his newest “old” possession home from The Green Butterfly on W. Miami Avenue.

He even kept the receipt, proving how he came into possession of the painting. The date of purchase: Dec. 4, 1999.

Caillouette knew Sinatra was an avid abstract painter.

“I was already 50 percent convinced it was by Frank Sinatra,” he said.

He began doing research on the painting’s signatures — one on the front and one on the back. He found a half dozen paintings in books with Sinatra’s name painted in white over gray, causing a shade affect. It’s the same on the harvest painting.

On the back was another story. Unlike the front “signature” in oil paint, the back one was signed using pencil in cursive, with the bottom of the “S” in Sinatra drawn out.

Sinatra used that style up until the late ’50s, when he changed how he wrote the “S,” Caillouette said. Caillouette learned this after he sought out a handwriting expert.

Al Wittnebert, out of Orlando, had co-written a small booklet on Sinatra’s signatures. In 2004, for $200, Caillouette hired Wittnebert to check out his painting. The expert concluded the Sinatra signature was genuine, and produced an affidavit which Caillouette would later use to help prove authenticity of the painting.

He finally had the proof he needed. It was, indeed, treasure. A rare Sinatra painting. The kind Sinatra used to give away to friends and acquaintances.

He took the painting to Thomas Cole on Hudson Street in Sarasota to remove some spotty mold and restore the artwork. And he scrapped the cheap frame that was falling apart and had it framed professionally at a local art store, complete with clear window panes on the back to view the unique signature and other writing on the back.

It hung in Caillouette’s house for awhile. Eventually he came across a painter’s box and stored the artwork for the next 15 years.

Every once in a while, as the Internet grew more substantial, Caillouette would research Sinatra’s art works and even photos of his home, searching for a photo or reference to the harvest painting.

“I never came across it,” he said.

Now semi-retired, Caillouette decided with a booming economy it was time to see what the artwork could fetch on the auction market.

He researched auctioneers and settled on Leslie Hindman Auctioneers in Chicago, which conservatively estimated the painting’s value between $5,000 and $7,000. Caillouette hopes the early Sinatra work, with its detail and its timing, will earn far more. The auction is next week.

“It’s a piece of history. It reflects what was going on back in the mid ’50s with Sinatra,” he said. “One of the most important features of the painting is the date, 1955. He was at his peak. Like his songs, the painting represents a time of richness and prosperity.”

It was painted shortly after Sinatra won the Academy Award for Best Supporting Actor for the movie “From Here To Eternity.”

The 16 inch by 20 inch oil canvas painting is of a shadow box filled with fall harvest items.

“At first glance, the box resembles a horn of plenty filled with several hanging ears of corn, wheat stalks, an apple, ripe concord grapes, tree branches with flowers, a pheasant feather and a gourd,” Caillouette said.

But it’s much more, he said.

“Some of the items cast shadows that create other elements within the painting. One of those is a shaded area resembling the facial silhouette of Sinatra,” Caillouette said. “It’s him. That’s what he looks like.”

Leslie Hindman Auctioneers in Chicago will hold a Post War and Contemporary Art Auction on Thursday, Dec. 13. The auction will include the sale of Caillouette’s Sinatra oil painting. The painting is lot 32 and it is listed as “Untitled (Still Life).” Exhibition of the painting at the auction house begins today (Sat., Dec. 8). Or, visit


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