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A Guide to Acquiring and Treasuring the Art of the Florida Highwaymen

This blog has been written and contributed by Dale A. Brill, Ph.D. (Group founder and administrator of the facebook group: Florida Highwaymen). It is with great appreciation to Dale Brill that we use this work as the inaugural blog in the launch of this website.
With the growth of Florida Highwaymen enthusiasts showing no signs of slowing, a guide to the landscape of the journey seems worthwhile. It is offered with the hope of generating contributions from others with different and deeper insights—even contradiction. This chapter, like the others, is a work-in-progress to be improved by the comments and adaptations driven by changes in the natural evolution of the Florida Highwaymen experience.
Consider this just one perspective among many possible takes. Word choice throughout the guide attempts to remind readers of the uniqueness of every Highwaymen painting acquisition. The use of “may,” “tend to,” and “often” signal generalizations not rules. Without exception, every interaction is different. Yours will be, too.

“MARKET VALUE AND PRICES”

Bottom line: A painting is worth what someone is willing to pay for it. That said, the value assigned to a painting is generally based on a calculus of several variables with two factors perhaps the most influential: recent sales prices and expected future demand.
Auction houses represent an easy opportunity to evaluate recent sales prices. Visit an auction house’s website and find their link to “Past Auctions.” From there you can evaluate recent “gavel prices,” which does not include the auctioneer’s premium or taxes. The premium is the auctioneer’s sales commission, ranging from 20% to 28%. Then add 7.5% taxes for state and local taxes (which vary by geography, of course).
Example: I “won” a Sam Newton painting at auction for $2,400. I ended up paying $3,096. The auctioneer’s 20% premium added $480. Taxes of 7.5% added $216.
What is the market value? Despite a gavel price (winning bid) of $2,400, the painting is “worth” (to me) $3,096.
In the example above, my experience and data analysis prior to the auction aligned with the auctioneer’s estimated or projected price which appears on the website. It seemed reasonable to expect the market value of the painting to fall between $2,000 and $4,000. That is a big range against which a painting can fall short or greatly exceed.
Calculations of “market value” can be influenced by several factors:
  1. The Artist
    1. Demand & Supply. Although there is no certainty about the number of Highwaymen paintings produced (estimates have ranged from 200,000 or more), readers exposed to the economic theory of supply and demand should recognize the impact that perceived scarcity—and other mental gymnastics—can have on prices.
      Livingston Roberts passed in 2004. Compared to the few remaining Highwaymen still painting, supply of his work is clearly limited. However, the “living or dead” criterion is but one factor. Another may be the length of time the artist painted, such as Poncho Moran who stopped painting early to follow the allure of being a professional gambler. As a result, the price of his paintings can rival Harold Newton but not from the perspective of artistry.
    2. Demonstration of talent. Not every painting reflects the artist’s best effort. The Highwaymen story is multidimensional, including the practical role of making money for the artists. The more they painted, the more they made. Paintings that are viewed as representing the artist’s full capabilities will command higher prices that may have been produced in a hurry to capture the opportunity represented by immediate demand from the tourist traffic during season.
    3. Style. Very similar to “demonstration of talent,” prices for Harold Newton’s paintings reflect, to a great degree, the degree of complexity and mastery demonstrated in his paintings. His work now typically requires investments of $10,000 or more. In contrast, Rodney Demps’ style is just now breaking the $1,000 threshold for exceptional pieces and less than $750 for direct purchases his more traditional work. Demps’ style, which might earn him the moniker “Dali of the Highwaymen,” appears at times crude in contrast to Harold Newton’s realism. Critics may conclude Demps had less talent than Harold Newton while fans may prefer to conclude that he simply saw Florida through a very different lens and it translated accordingly through his paintings.
  2. Scene. Paintings featuring poincianas might be considered the quintessential Highwaymen scene. After several hundred, you start to see the common themes featured across all 26 painters: Rio Mar, River Road, River Inlets, etc. Within a painter’s portfolio, there will be scenes that are featured more than others. For example, Al Black’s work features three birds in flight for the Trinity (although older pieces do not seem bound by this trademark element). Willie Daniels has produced many river/inlet scenes, each with skeletal dock pilings emerging from the shore. Demand for a scene that diverges from those typically associated with an artist often command higher prices. A Willie Daniels piece that features other components, such as a building or person, can be attractive to collectors looking for variation it creates.
  3. Size. Jumbo or larger pieces (e.g., 24 x 48) command more than smaller pieces (e.g., 16 x 20) generally as the greater space tends to impact the complexity of the work and featured scenes depicted.
    One Florida Highwaymen collector has speculated value (sales price) using a standard calculation based on the surface area of the painting. Example: a 16 x 20 painting by Harold Newton would have a surface area of 320 square inches. At a calculated value per square inch of $17.00, the painting would be worth $5,440. Such an approach as this, of course, would need to reflect trends in sales over time to adjust the “value per square inch” and take into consideration the subjective factors addressed elsewhere in this guide.
  4. Medium. The quintessential media associated with Highwaymen paintings are Upson and Masonite board found on construction sites and the local lumber yard. In fact, painting on Upson is considered by expert Kathleen Piowaty Fredrick to be a criterion for inclusion as an Original Highwaymen. Those artists painting in the same style today missed the necessity of Upson and Masonite. Canvas had long been a luxury; as a result, canvas tends to signal the difference between “early” and “later” paintings by the same artist.
  5. Timing. If buying at auction, note that the prices appear to soften during June – August when the Snowbirds (Northern residents who flock to Florida for the winter) return home. The premise is that the drop in high-tier (read: money) demand softens bidding at auctions; and otherwise puts on hold the buying from local galleries or individuals. My theory suggests that supply then builds up until the late fall return of buyers and the corresponding increase in the frequency of auctions creates the perceived scarcity in March and April. Surely somebody can check me on that.
    Another timing dynamic is consistent with any the first rule of negotiation: The side that can live with the answer being “no” has the upper hand: Buyers in a hurry to secure a painting tend to negotiate less and pay more; and sellers in no hurry to part with a piece tend to be better at resisting low offers.
  6. Source. Although the tide is turning, few are the buyers willing to spend $4,000 or more without personally laying eyes on the painting. This has a general effect of chilling overall demand. Exceptions include transactions from trusted sources, such as the auction houses in Vero Beach and elsewhere in Florida, or sellers with whom a track record of quality are established or willingness to accept returns, which is a recommended criterion for purchasing a painting on eBay.
    Galleries tend to demand higher prices than private sellers or dealers with costs such as rent, staff, and utilities. It is not uncommon to see a painting purchased at auction for $2,250 offered weeks later at a gallery for $4,750. Dealers operating out of their homes, vehicles, or eBay often provide opportunity to save money, but the risk can be greater than a gallery with a brick-and-mortar presence with greater exposure to reputation damage if a customer isn’t happy. Finally, private sellers represent the best opportunity for the best pricing. It’s almost too rare to mention now but finding a Highwaymen painting at a thrift store or neighborhood garage sale is not entirely out of the question. A significant source of supply comes from family members who find themselves needing to find homes for pieces from a deceased loved one’s collection. These sellers are highly coveted by auction houses, dealers, and direct buyers alike.
  7. Motivation. Investors willingness to pay differs from collectors with even greater variation seen among enthusiasts. Investors are motivated to maximize the return on investment–buy low(er), sell high(er). Investors will be more aware of demand and trends in prices with limits tied to the likelihood of getting the targeted profit margin at resale.
    Collectors may be in the market to feed their obsession or complement their existing portfolio with work from a missing artist. A unique scene or prevalence of a coveted technique combined with enough disposable income can blow the expected price range out of the water, especially when two collectors are locked on the same piece.
    Enthusiasts tend to buy what they love with an eye on the budget. While a jumbo Harold Newton may be out of reach, a smaller piece by another artist becomes a family treasure and conversation piece for years to come.
All things evolve. Fluctuations in the economy and disruption created by technology integration, such as virtual reality and the metaverse, will surely push the artworld across new horizons. The Florida Highwaymen experience will change with it, and the landscape described in this guide will need to reflect adaptations.