The Original Highwayman's Self-Portrait
Discovered and Sold!

by: Bob Leblanc

As seen in Antiques & Art Around Florida, Summer/Fall 2008

On a bright and beautiful Sunday morning, a few days into Chanukah and a few weeks before Christmas, a deal was struck in the parking lot of a prison in West Palm Beach. Somehow the dreary backdrop of chain link fences and barbed wire seemed appropriate, as the handshakes and solemn looks went around and the product changed hands after the final negotiation.

The sometimes romantic history of Florida’s African American highwaymen and their art is woven with darker tales of prisons and misfortune, segregation and intolerance, salesmen and con-men, suppression and hard times, drugs, excessive drinking and attempts to avoid the authorities.

The parking lot transaction involved perhaps the most important highwayman painting to surface into the art market since the story of these artists and their paintings began to be reported in various publications a dozen years ago.

This particular painting, by the artist generally acknowledged as the most accomplished in the group of twenty-six immortalized in the Florida Artists Hall of Fame in Tallahassee, is not only the highlight of one of the most important collections of highwaymen art, but also, quite possibly, the crown jewel of the entire genre.

Executed on a vintage canvas board dating back to the fifties or sixties, in a perfect viewing size, and in its original hand-made crown molding frame, is a self-portrait of Harold Newton. “The original highwayman” is seen sitting on the steps of his porch, head thrown back, bottle to his lips, quenching his unending thirst, while enduring the nagging he had to listen to due to his fondness for drink.

A completely understandable fondness, but not everyone understands. Certainly not “Mama”, hands on her hips, big old booty behind her, looking her intimidating best as she stands, solid and imposing, behind him, glaring daggers into his back as he takes his swig.

Harold Newton was a man of immense talent and immense appetites. Both are displayed for all future generations to see.

 This painting may be Harold’s ultimate statement as to whom exactly he was in his life without a paintbrush or palette knife in his hand. His legacy of being his own man and doing whatever he pleased, despite the consequences, was recorded that day decades ago, by his knife and oils. The dark and ominous clouds in the background of the painting metaphorically represent more than the incoming stormy Florida weather. Looks like an incoming stormy “Mama”, too. Might be time to go back on the road and live in his trailer for a while. Papa was a rolling stone, after all. Wherever he laid his hat was his home.

An important part of southern cultural history portrayed in artistic form, it is thought provoking as well as visually balanced and pleasing to the eye.

This work is more than just a masterpiece of Florida’s regional highwaymen art, it transcends that genre. It is true American folk art, outsider art, that which is defined as having been painted by a self taught artist.

Harold was indeed self taught. Influenced by A. E. Backus, the successful and prolific studio artist, Harold was not given formal instruction, but most likely friendly suggestion. He took no lessons but certainly learned from his observations of Backus’ execution on canvas. He must have been encouraged by the camaraderie afforded him by “the dean of Florida land-scape artists”. Backus’ many gifts to the art world included introducing young Mr. Newton to a more universally desirable and marketable product than his most recent portraits of Jesus on black velvet. Harold was a man who was not only gifted with artistic talent, but was fortunate enough to discover that combined with an aggressive, yet politically careful sales approach to the public, he could make a successful living by utilizing this gift to paint the Florida landscape. He likely didn’t care that he was also recording Florida history, just enjoying his work and trying to make a few dimes.

This special painting first surfaced into the newly born highwaymen art market, in West Palm Beach at the Piccadilly antique show sometime in 1995 or 1996, displayed prominently as the only painting in a non-art dealer’s booth along with her glass and china in the old “building one” of the Florida State Fairgrounds. Ironically, this building is only a stone’s throw from the aforementioned prison parking lot.

Looking back, this was a time of discovery, when a cork board with a few yellowed clippings from local newspapers such as the St. Petersburg Times, and Jim Fitch’s full color images in Antiques & Art Around Florida was the only real proof a dealer could show to educate the public that such a market as “highwaymen art” was recognized in the collecting community.

Fitch’s article in the 1995 Winter/Spring issue of Antiques & Art Around Florida loosely defined the market as works by a group of African American artists from the Fort Pierce area who employed a door to door sales approach while traveling the state, their paintings, still wet, stacked in the trunks of their cars or in the beds of their pick-up trucks. It would be about five years before Gary Monroe would begin his research, ironically again, with interviews of highwaymen art dealers in this very same “building one”.

At that time, the mid-nineties, very few fellow Florida regional dealers, especially art dealers, would pay attention to these often shabby looking, sometimes amateurishly executed paintings of Florida’s lush landscape. “Too garish”, they would opine. Or, “Too dark”. Or, “Look at those awful frames”. Or, “You get that out of a dumpster?” The few active highwaymen dealers and collectors in those days could be counted on one hand. We were usually able to buy a couple of full size attractive paintings by most of these artists for $40.00 or less, and have a third one thrown in for free. The market value prices in the mid-nineties was still about the same as the artists had charged for their pieces originally in the 50’s and 60’s. They were affordable and easy to find. In fact, there were so many of these paintings around that finding and purchasing them was never a problem. The supply was evident, but the demand was just barely beginning. Most of them were very difficult to sell for $35.00 or more. Occasionally a potential customer would come along, find one appealing and could be talked into the investment. Actual knowledge as to what was good and what wasn’t within the genre was only beginning to accumulate. Powerful seascapes by Alfred Hair, gorgeous sunsets by Roy McLendon or Livingston Roberts went begging at $50.00 to $75.00.

Newton’s work, however, was usually recognized by anyone with an appreciation for art as being more valuable than most work by the rest of this group. Harold’s paintings were simply better than the rest.

Harold Newton’s art always commanded a premium over the other artists’ work, even back then.

Such was the case in “building one” a decade ago. When a gorgeous landscape by Harold could bring as much as $200.00 or even $300.00, (but surely no more than that), this non-art dealer had such an affinity for this particular work that she insisted on pricing it at the audacious level of $800.00.

Knowing the intricacies of the Harold Newton market as well as I thought I did, and having had the experience of having seen maybe a few dozen of his paintings at the time, maybe had bought and sold a couple, I was much too savvy to buy it. Why over-pay ? Good Lord, I could buy larger, much more bright and beautiful Harold Newton paintings for much, much less. And they were available. This small painting had a dreary feel to it, dark sky, stick people spoiling the picture for heaven’s sake, and the poinciana tree wasn’t even in bloom. I mean, it had a value, sure, but $800.00? It was just too different from what I had become used to seeing  by these artists, and way too expensive, even for a Newton.

 “The dealer must be out of her mind”, I thought. She wants a record price.

 I knew no one would buy it, and no one did.

But the non-art dealer had the proper instinct. She, and only she, was smart enough to fully appreciate the importance of this work from its proper perspective at that point in time. She kept it, hung it at home where she could enjoy it, and decided to just wait and see what would happen with this fledgling highwaymen art market over the course of the next ten years. She took it off the market, no longer available for sale.

As we all gradually became educated in the next five years, we also were exposed to more and more Newton paintings, both to study and to keep track of. The demand for Harold’s work was consistently increasing as the art buying public became more knowledgeable due to articles in more and more Florida periodicals. The rarity and importance of vintage  highwaymen paintings with people featured in them, particularly by Harold, became evident. Jim Fitch wrote an article in Antiques and Art Around Florida in the 2000 Summer/Fall issue featuring the representation of people in Newton’s work. Desirability of these pieces sky-rocketed as did their values. As each newly found discovery changed hands, new price records were set. An extremely specialized supply and demand market, within a broader market of vintage highwaymen art, was in full swing. Harold’s people pictures were leading the way.

Then, about five years later, around 2004, armed with up to date knowledge of the value and liquidity of Newton’s people pictures, I somehow remembered this unusual painting of a man sitting on his front steps, drinking from a bottle. I began to call the now retired non-art dealer to inquire as to its availability.

I’d get an answering machine, leave a message, then I’d let six months go by and try again. I was persistent, possibly a pest, for several years, albeit a pest only for a minute or two. Finally I got through, a live person answered the phone. It was she, the now retired non-art dealer herself. I could hardly believe it. Yes, the painting was still in her possession, but not yet for sale. Apparently my persistence made its mark as she then promised to allow me to handle the liquidation of the painting when she decided the time was right.

The time became right that sunny December 2007 morning.  She had done her research and was comfortable naming her asking price.

That prison parking lot adjacent to the South Florida Fairgrounds, just off Southern Boulevard where the West Palm Beach Antiques and Collectibles show is held, was where the buyer, the seller and the broker met. It was a secure location, affording privacy in a public location. After a careful inspection by all involved parties, and some perfunctory discussion, the painting found its way to an extremely appreciative new owner, Fort Lauderdale attorney, Scott Schlesinger.

Schlesinger, a patron of the arts and owner of a very impressive Florida art collection, has been at the forefront of the highwaymen collector market since becoming a deep pocket player at highly visible public auctions. It was not uncommon for him to establish new price records for extraordinary highwaymen “people” paintings as far back as seven or eight years ago. He has consistently been aggressive in his quest for the rarest works by Harold Newton and Alfred Hair. Fair, yet realistic as well, he understands that the best of the best always commands a premium.

More recently, he was the driving force behind the magnificent exhibit of art at the Museum of Art / Fort Lauderdale, and the wonderful catalog of rarities that it generated, “Highwaymen Newton & Hair, The American Dream in the Sunshine State”.

The buyer, Schlesinger, maintains the website,

The seller is respectfully granted her request for anonymity.

About the author:
BOB LEBLANC —The broker and author of this story maintains the website, and the new inter-active website,

Bob LeBlanc has been a full time dealer in collectibles for nearly four decades. His work was first published nationally in “The Coin Dealer Newsletter”, or “The Greysheet”, in September 1979 when his area of expertise was the rare coin market.

 His focus shifted to highwaymen art upon the publication of Jim Fitch’s first AARF article in 1995. He began to buy and sell highwaymen art at that time. Since then he has been educating the public and promoting this market by exhibiting at antique shows around Florida.

 In 2001, he established his website and soon recognized a need and initiated his certification service for authentication, attribution and appraisals of highwaymen art as these paintings have become more valuable and subject to dishonest representation. He is endorsed by The Safety Harbor Museum of Regional History, among others, for his knowledge, experience and integrity.

 Bob’s philosophy is to deal primarily, although not exclusively, in eye appealing vintage pieces by the most accomplished artists in the group. His belief in investing in quality over quantity has never wavered.


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