The First & Original Monthly Highwaymen Blog

The month of May was a quiet month for the Highwaymen market. There were only two relatively small auctions, and the passing of the colorful and legendary Al Black has also put a short-term damper on activity. I would also point out that the month of May is the historical start of the “low season” in the Highwaymen market, as a large number of collectors start the annual exodus from Florida for the summer.

Auctions this month included:

Vero Beach Auction May 17 43 Highwaymen paintings with target value: $97,500
Manor Auctions May 24 52 Highwaymen paintings with target value: $139,750

As a basis of comparison and indication of the slow month, these auction metrics compare with March 2025 numbers as follows:

Vero Beach Auction 48 paintings with target value of $92,200
Manor Auctions 60 paintings with target value of $ 202,600
Rennick Auctions 114 paintings with target value of $ 372,950
FL Highwaymen Auctions 41 paintings with target value of $ 111,450
Total target value of 95 Highwaymen paintings auctioned this month (May):$ 237,250
Total target value of 263 Highwaymen paintings auctioned in March 2025:$ 779,200

These data indicate that the market had approximately triple the number of paintings and value auctioned during March, as compared to this month. Clearly, this is a slow month, and sales results were reflected in this slower environment.

Note:  because of the relative strength of the market in March, as compared with this month, there were two additional auction houses (Rennick and FL Highwaymen) holding auctions in March.  Rennick will not hold their next auction until November, and FL Highwaymen Auctions will do their next auction in July, following a 4-month break.

Sales Results of the Two May Auctions:

The first auction of the month was Vero Beach Auction. Target price estimates seemed reasonable, and there were several attractive paintings being offered. Highlights of the sale included the oversized  (30 x 40) James Gibson, with very heavy palette knife work. The Gibson had the highest hammer price of the auction.

30x40 on Canvas; Target $5,000 / Hammer $8,000

Other highlights included a group of 4 paintings by Robert Butler. Apparently, all coming from the same collector, each having a beautiful, original pecky cypress frame.  High quality Butler paintings like these have become more and more rare.

22x26 on canvas; dated 1973; Target $2,500 / Hammer $3,500
24x48 on canvas; Dated 1971; Target $5,000; Hammer $5,000

Other highlights included a group of 4 paintings by Robert Butler. Apparently, all coming from the same collector, each having a beautiful, original pecky cypress frame. High quality Butler paintings like these have become more and more rare.

Overall, the Vero Beach auction had total target prices of $97,500 and a hammer price total of $99,625. I would characterize the auction as successful, with total results exceeding the estimates.

The Manor Auction was held the following weekend.  I would characterize the auction as slightly larger than Vero (although still small). The auction had many paintings with unusually low estimates, and no paintings in the auction had an estimate higher than $10,000.

The auction had total target prices of $139,750, and brought total hammer prices of $143,950.  Like Vero Beach, the auction sales results were slightly higher than the total target prices, with no paintings passing in this auction. Again, I would say this auction was a moderate success.

In a similar trend as at Vero, the Harold Newton paintings performed poorly.  Of the 6 Harold Newton paintings offered, 5 did not reach the target price.  The auction was also characterized by 15 Sam Newton paintings – an unusually large number given the auction had only 52 paintings.  The Sam Newton paintings represented 29% of the entire auction !  They were all essentially “average” paintings, with none reaching a hammer price of $5,000, and the average hammer price of the 15 paintings only being $2,900.   While not a poor performance, it certainly was not an exciting result.

Sales results at the Manor auction may have been negatively affected due to the auction being moved to 4pm, to allow people to attend the Al Black funeral which had been scheduled earlier on the same day.  The auction house had fewer live bidders than usual, but the online bidding audience seemed to be a bit larger than normal.  Nonetheless, I believe the less-than-exciting auction results were a function of the auction having essentially all average paintings.

Two very nice, and relatively well performing paintings included an early Al Black on upson (nicely muted and refined – not so typical for Al Black) , and a small but very nice Lem Newton.  The auction had 4 Al Black paintings, with 3 of them selling for more than $1,000.  An unusually strong result, which may be an indication of a coming price rise in Al Black paintings.

24x36 on Upson, Wetland Wonderland Target $1,000 / Hammer $1,500
18x12 on Masonite; Peachy Perfect Target $1,500 / Hammer $1,900

The Market:

This month, these two auctions have sent a very clear message.  Bidding levels are not where they were a few months ago.  Auction activity (both the number and quality of paintings) is not where it was a few months ago.  Of course, some may say it is just a function of the traditionally slow summer season beginning. However, I believe there is a softening of the market that goes beyond “seasonality”.   

The Highwaymen market seems to be finally catching up with the economy, and the economic pressures that many people have been facing.  Consumer prices of everything are up, leaving less money for the “painting every month” approach of many collectors.  I am not suggesting that collectors are not buying – but buying has clearly slowed down.  The collectors who used to buy paintings every month are now buying a painting every 2 or 3 months.  It’s affecting the market.

At the same time, many collectors are now undertaking a serious review of their collections to determine if there are paintings they should sell to slim down what has become a “bloated” collection.  These collectors are not selling for economic reasons – they simply, and typically, don’t even have room to hang all their paintings.  They acquired too many paintings in the last 3-5 years, and now they are selling some.  

There are also many “owners” of Highwaymen paintings (not collectors) who have decided to sell their paintings because they simply need the cash.  These painting owners are often people who have had 1 or 2 paintings for many years – often acquiring them from parents or relatives who have passed on.  They have held on to the paintings often for sentimental reasons, but now they are selling.  I can say that as a dealer, the number of calls from these “owners” have increased dramatically in the last 6-8 months.  I’m sure the auction houses are also receiving these calls.

Finally, the tried and true fundamental economic theory holds steady.  When supply goes up, prices go down.  There is no doubt that the supply of paintings in the market has increased quite significantly in the last year.

Harold Newton has always been considered a barometer of the market.  When the market has gone through periods of strong growth, Harold Newton’s prices were always leading the way.  But now we are seeing Harold Newton hammer prices performing poorly relative to estimates and target prices.  This month, 2 of the 3 Harolds passed at Vero.  At Manor, 5 of the 6 Harolds did not reach the low estimate.  These are not random results.  The market is being impacted by all the factors I have discussed above.

This does not mean that all Highwaymen art and artists are affected the same way.  The fact is there are some Highwaymen artists whose prices are softening (a trend that actually started last Fall), while there are others who are strengthening.

Clearly, Harold Newton has seen a major softening.  That is not to say that a top 5% Harold will not sell for a significant price.  But the average paintings are suffering.  A year ago, you could not find a full size Harold for less than $5,000.   This month, 2 Harolds at Vero Beach (each full size at 24×32) did not receive an opening bid of $4,000.

Sam Newton has also been affected by the same factors, but unique to Sam. The market has been flooded with his paintings to an extent that it is creating downward pricing pressure.  (It’s that pesky old supply and demand theory that can’t be ignored).  Having 15 Sam Newton paintings in an auction with only 52 paintings (essentially 30% of the auction), does not help the market, and does not help the prices for Sam Newton paintings.

Other artists that have been exhibiting weaknesses include Willie Daniels and James Gibson (also too many paintings coming to market).

At the other end of the spectrum, artists with continued strength and demand include Robert Butler, George and Ellis Buckner, and to many collectors’ surprise, Rodney Demps.  Of course, several artists also retain strong pricing due to rarity, including Alfonso Moran, Charles Walker, and Willie Reagan.  These three artists are rarely seen in the auctions, and are not generally available through dealers.  Thus, their rarity continues to drive strong prices. (Once again… supply/demand).

Where Is The Market Heading?

I believe we will continue to see a soft market through the summer and early Fall.  Hopefully, we will not see auctions with 15 Sam Newton paintings, or more auctions filled with only average quality work.  It seems to me that as recently as 12-18 months ago, most auctions had some very exciting paintings being offered.  Just a few top quality paintings is enough to get collectors excited about the market and a particular auction.  But when collectors only see paintings that they feel they have seen many times, the interest level wanes.

The November sales always seem to get everyone excited. Snowbirds are back, and the Rennick Auction has had 8 months to put together a high quality selection of paintings which always delivers.  Until then, this is still a good time for collectors and dealers to be looking for selected bargains in the market!

Coming up in July there will be another auction by Vero Beach Auction, as well as Manor Auctions.  Additionally, we will have an interesting auction July 4 weekend (on Saturday July 5, 12 noon) by Florida Highwaymen Auctions, to be held at the Ft. Pierce Yacht Club.  This is the same company that held the major auction this past New Years weekend at Magnolia Manor in Vero Beach. They are continuing their tradition of a free steak and lobster lunch!  And, I know they are working hard to bring a large selection of high quality paintings.

And – don’t forget the summer parties and Highwaymen sales at This Is It Café & Gallery !! 

Our next event at the Café & Gallery will be June 7, 4-8pm.

BIG NEWS !! …..  For all those who could not make it to Orlando for the Mary Ann Carroll Retrospective Exhibition – On June 28, 4-8pm – we will open a 2-week MAC exhibition at the Café, which will include 25 of the 40 paintings currently on exhibition in the Orlando exhibit.  There will also be a selection of Mary Ann Carroll paintings for sale, which were in the Orlando exhibition. 

The café is located at 444 24th Street, West Palm Beach.

Until then ….  Happy Hunting !

Mark Lerner
786-599-5816
MJL@TheHighwaymenCollector.com
www.TheHighwaymenCollector.com