Antiques and Art Around Florida — 2010-2011 Issue
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Who Is Freddy? A Highwaymen Mystery Solved
Bob Kealing

G eoff Cook bought his first “Freddy” for all of $35.00 It was Spring of 2003 and by that time Cook was five years in to his all-consuming love of Florida Highwaymen art. While Cook was trolling for paintings at a garage sale in Stuart, the owners pointed out an unusual one on the wall.

“I had never seen a Freddy painting before but really wanted this one for the collection,” Cook recalled. “Not just because it was worth more money being a Freddy painting but it had people in it too!”

The couple was at a loss to put a value on the mystery Freddy piece.“They told me that a dealer had been out from town to price things for them,” said Cook, “But nobody knew anything about the Freddy painting.”

Cook knew just enough to know that once in a while, one of the earliest Highwaymen painters Alfred Hair signed his work as Freddy.

When the owners offered to let this one go for $35 Cook didn’t hesitate. He felt a fair amount of certainty he’d just bought an Alfred Hair painting “for peanuts.”

The countless hours Cook invested traveling and searching, this time had paid off.

Now and then, other Highwaymen painters have been known to sign their work under assumed names. Al Black sometimes put his nickname “Blood” to a painting. John Maynor has been known to scrawl the name “Lil John” on some of his work.

But to this day the Freddy mystery lingers. It’s still subject of considerable discussion and speculation.

There are dozens of Freddy paintings out there floating around. Why did Alfred Hair assume a ghost name?

Even Kelvin Hair, Alfred’s son and himself an artist isn’t sure. “Bill collectors may have been after him,” Kelvin speculated.

Another original Highwaymen painter Al Black offered another theory: “Alfred signed his paintings Freddy back in 1961 because the repoman was after his Cadillac.” But Black didn’t become part of the Highwaymen movement until 1963 or 64. His thoughts are also pure speculation.

There’s yet another urban legend that a furniture store owner by the name of “Freddy” wanted his name signed so he could claim credit for the paintings.

To get to the bottom of the mystery, we consulted Alfred Hair’s widow Doretha Hair Truesdell and her brother Carnell “Pete” Smith, a Highwaymen painter who was also a salesman of Alfred Hair’s work.

“Alfred and I painted most of the Freddy paintings together,” Truesdell said. Hair was known to mass produce his work quickly to make the most money possible. Unlike some of the other Highwaymen, this was Hair’s only means of making a living.

Because Hair was so prolific, his mentor AE “Beanie” Backus suggested he adopt a ghost name for some of them. “He said he was selling too many paintings with his name on them,” Truesdell recalled, “and was cheapening the work.”

Hair had learned how to paint from Backus, then plied the doorto- door sales technique of another legendary Highwayman artist, Harold Newton.

Hair painted fast grass and lived to turn a quick buck off his art. As collector Geoff Cook noted, “Harold took more time with his work, choosing to be more deliberate with his ability to conceive realistic, rather than fast art.”

According to Smith, Doretha would start some of the basic elements of Hair’s paintings like the sky and the foreground. “Alfred would come back and finish them up,” Smith said, “Adding details like trees, shadows, birds, and people.”

Hair signed his collaborative works with Doretha under his ghost name- Freddy. Smith added that the ‘d’s in Freddy were Hair’s tip of the hat to his wife.

Of special interest to collectors, Truesdell estimated that only 75 or fewer Freddy paintings in total were produced by the husband and wife team in 1966 and early 1967.

Now that we know the solution to the Freddy mystery, it adds yet another layer of mystique to Alfred Hair, one of the most celebrated and tragic Highwaymen of them all.

Just three years after completing his work as “Freddy,” Hair was gunned down during an altercation at a Fort Pierce bar named, “Eddie’s Place.”

His friend and fellow Highwayman Livingston Roberts stopped by Hair’s home to see if he wanted to step out for a drink and a game of pool. Hair asked Doretha would she mind if he went?

“If I had told him not to go he would still be with us,” said Truesdell in a voice still reflecting the sorrow of that day. It was 1970 and Alfred Hair had not yet turned 30.

Today the hundreds of paintings he produced under his own name, as well as his “Freddy” collaborations remain Alfred Hair’s legacy-so too is the work being produced every day by his son Kelvin Hair

Hair’s legacy and the story of the Highwaymen continue to be celebrated on a local, regional, even national level.

In 2005, The Historical Society of Central Florida published, Florida’s Highwaymen: Legendary Landscapes featur ing eight original Highwaymen and the Geoff and Patti Cook collection of their work. Author Bob Beatty tells the story of Alfred Hair, Harold Newton, Al Black and other young African - American painters trying to make their way as artists in the still-segregated south of the 1950s and 60s.

If you’d like to see one of Cook’s “Freddy” paintings and treasures by all twenty-six Highwaymen artists, you’ll get that chance beginning September 25th.

The Orlando Regional History Center’s new Highwaymen exhibit and the story of their rise from menial citrus picking jobs to celebrated artists entitled, “Against All Odds” kicks off a national tour in downtown Orlando. It’s the History Center’s third traveling exhibit of this unique Florida art tradition.

Thanks to the national exposure, and active buying and selling on eBay and other auction sites, Highwaymen secrets like “Freddy” are getting harder-and more expensive-to find.

But for avid collectors like Geoff Cook still willing to put in the miles, each early morning hunt, every garage sale scoured holds a glimmer of hope that the next Freddy treasure is out there.

An Alfred Hair by any name is still a steal at thirty five bucks.