A Tale of Two Pictures

by: Bob Leblanc

As seen in Antiques & Art Around Florida, 2012-2013

Back in Medieval times, probably 1996, not long after I had invested in about 15 highwaymen paintings that Jim Fitch had released from the Museum of Florida’s Art and Culture, good old MOFAC, I was travelling east from home to the West Palm Beach Fairgrounds show and this time I used state road 70, through Okeechobee.

Just before the downtown area, I spotted a little cracker shack on the left with a sign, "Antiques".

So, of course, I pulled into the dirt and gravel parking lot in front.

It was a small place with a sort of cubby hole entrance which led to a main room and 2 smaller ones. They were jammed with the usual flea market crap that we see all the time in places like this, dusty glass, pottery, old tools, you get the idea.

On the wall were the usual valueless (to me, at least) decorative prints and some Walmart type paintings and giclees, but not far from the entrance hung two oil paintings that I recognized as obvious highwaymen in original crown molding frames. Upon closer inspection, I saw they were both signed "C. Wheeler".

I had not seen any of Chico Wheeler’s work until that day, and in my naivete, thought they were very scarce at the time. Most of what I had previously seen and handled were Newtons, Hairs, McLendons and Al Blacks. With only a half a year’s worth of experience in studying and trading in this newly born market, I was excited to discover Wheelers in what I thought was an out-of-the-way place.

The group of twenty-six had yet to be defined by the author of the first highwaymen book, and all we dealers had to go by was Fitch’s approximation of about 20 artists.

One of these paintings was bright and pretty, as shown, one was dark and ugly.

Now, I was still learning about the highwaymen, at the time there were only a couple of articles written about them, (Fitch and Klinkenberg the authors), which I clipped and stapled to a cork board that I hauled around to shows to expose the legitimacy of this collectibles market.

I knew from 20 years experience as a rare coin trader how to go about the business of "buying" so I quietly asked the proprietor, "How much are these?"

In a situation like that, it’s counter-productive to show off one’s knowledge by saying, "Oooh, highwaymen oil paintings. I know all about these things, what are you asking for them?"

The paintings were priced at $40 or $45 each, so I negotiated and bought the pretty one for $35.00, comfortable in the idea that I had found a rarity and would do fairly well re-selling it.

I wasn’t chuckling on having scored big-time, just happy to have added a different artist to my inventory. A small one, 24x18, so plenty of room for it in my booth at the upcoming show. If I got lucky, someone would like it and maybe it would move on to a new collector’s home.

Figured I’d price it at $100.00, let someone beat me down to $75.00 and double my money. If I had thought it was a phenomenal deal, I’d have bought both of them, but I didn’t.

Little did I know that this would turn out to be one of my all-time favorite deals.

So I mixed it in with the other highwaymen paintings I displayed for sale at the show, and a favorite little customer, by the name of Sandy, fell in love with this new little Chico Wheeler. She was, at the time, on her quest for one by each of the highwaymen on whatever the current list was at that time.

She had brought with her, to the show, an extra painting that she had picked somewhere for $100.00 if I remember correctly, had re-framed, and didn’t feel it was pretty enough to keep in her collection, and besides that, she already had another one by this artist, so it was expendable in a trade.

Happened that her extra highwaymen was a Harold Newton, the seascape you see posted left.

It was on canvasboard, which was unusual from what I had seen by Harold, upson board and masonite being the norm. It was also an unusual size, 22 x 30, different again from what I had seen up to that point. I wasn’t crazy about it at first, but I was willing to make a deal for it.

I offered her the Chico in trade for $100.00 plus her painting.

She surprised me and said, "OK", and I started singing "Happy days are here again..."

No, not really, but both sides were happy. Sandy had a new piece for her collection and I had a free piece of inventory.

No one showed any interest in my newest Harold for several months, so I hung it up at home to let it age.

It aged like a fine wine.

Every day that I saw it, I liked it a little bit more. It was one of those paintings that "grows on you". Highwaymen art is like that.

After about a year or two, I brought it back onto the market and Ty Tyson fell in love with it. Ty and Jean Tyson were rocking along with their gallery in Micanopy, specializing in highwaymen, and they had become one of my most reliable customers. At least once a month I’d go visit them and we’d trade a dozen paintings back and forth, I’d buy some of theirs and they’d buy some of mine. The Florida regional economy was different before that infernal year of the hurricanes, and business was thriving at that time.

So, Ty bought it for $2000.00, which was fair at the time, and hung it on his bedroom wall for a couple of more years before he got tired of it. He called me, and I bought it back from him for the same $2000.00 that I had sold it for. It sold almost immediately to a Miami attorney for $3000.00 which was also fair at the time.

Unfortunately for him, he held it for too many years and finally sold it on eBay for, I think, $1500.00. Life can be like that. It’s the timing that can come up and bite you.

Collectibles markets, with values ruled by economic laws of supply and demand, can teach one some hard truths about market cycles as affected by the general economy. When discretionary income disappears, average people stop purchasing things they don’t really need. Wealthy people who have been interested buyers take a "sit back and wait" attitude because they believe it could get worse allowing them to put cash into the same product at even more favorable prices. Demand is down. With a fixed supply and a shrunken demand, prices must be lowered in order to initiate sales. Values suffer in comparison to past achievements.

We are all learning this lesson right now, proven beyond a shadow of a doubt by recorded prices realized at the simplest tracking point, public auction.

Highwaymen art is not a fad, it’s a sustainable viable market.

Beanie Babies were a fad. That fad burned brightly then just as quickly turned into smoke and blew away in the breeze of the next fad. As a collectible market, it came and went in a year or maybe two.

Collecting and therefore investing in art is a centuries old tradition, used to calm or excite lives by decorating living quarters. Demand for visual enhancement of the home has forever been present though out history. The public perception of the times we live in determine whether the demand is strong or weak. But demand is always there for eye appealing landscape art.

Florida’s highwaymen art is a collectible market with staying power. It is a currently small regional market, a sub-market connected to a number of larger markets, namely investment quality fine art, folk (outsider or self-taught) art, American landscape art, African American art, historical Florida art.

On the bright side of the coin, market cycles are just that, cycles, like the wheels on a bicycle. They go around and around. We expect the highwaymen market, when purses loosen up, and demand increases, to not only reach its previous peak, but to surpass it. History shows this to be expected. Around here, we believe an excellent buying opportunity exists for owning and displaying a bit of Florida’s history in high quality highwaymen art.

About the author:
For four decades, Bob LeBlanc has been a full time professional trader in collectibles. Since Jim Fitch’s original AARF article on the highwaymen in 1995, he has focused on vintage works by the more talented artists in the group. In 2000, his main web site,

www.highwaymen-buy-sell-trade.com was established, recognizing an emerging highwaymen market necessity. In 2003, he established his authentication, attribution and appraisal service. His expertise in evaluation has been used by museums, attorneys, auction houses, dealers and collectors for close to a full decade.

The author of several published articles on Harold Newton’s work, Bob also maintains several blogs and Facebook pages featuring highwaymen art, news and educational links. Since 1996, he has been a permanent dealer of highwaymen and other fine art at the West Palm Beach Antique Festival, where he offers free highwaymen art appraisals.


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