Fast Painting,  Slow Reading

It’s an interesting challenge to do a round-up evaluation of the Highwaymen artists for the last year.  The year has been an interesting one which has not followed the simple patterns of years past.  Historically, most artists have moved in synch… when the Highwaymen market was moving up slowly, all the artists seemed to be moving up slowly, etc.  When it was moving up quickly, likewise, the artists all seemed to move in tandem.  But this year we have seen trends where some of the artists have seen their prices dropping, while others are increasing.   It is actually a sign of a maturing market, and greater maturity on the part of many of the collectors.   No matter how good Harold Newton may be, collectors have realized that his prices have gone up faster than the market in recent years, and there is still an overabundance of his paintings coming to auction every month.  Under this scenario, prices cannot keep going up faster than the general market, and as a result, there has been a clear correction in his prices.  The Highwaymen market is starting to act like any commercial market, based upon supply and demand.  When the supply keeps coming, or even increases, and demand remains relatively stable, we all know what the supply curve says will happen …. falling prices.  The Highwaymen market is not immune to basic economics, despite what I regard as self-serving preaching about continuing price increases by many of the markets major dealers and auctioneers  (The “Elders” as I like to call them !)

To start this year-end discussion, I thought it would be interesting to report on each artists highest valued painting sold this year at auction.  When looking at this, it’s a useful to remember that 2025 saw more than 1,500 paintings at auction, and these are the single top prices for each of the 26 artists.  It sets a general bar or ceiling for where the high point is, although it should be pointed out that many of these artists have had paintings sell in the private market for higher prices than these.  Of course, we don’t know what those are except those that we have sold for higher prices!  

In the case of Harold Newton, we have all heard the stories from the “Elders” of paintings selling in the private market for $100,000, but the auction market indicates that the top sale this year did not reach a hammer price of $50,000, and in fact, there has never been a Harold Newton painting at auction that has reached a hammer price of $50,000.

Likewise, for some of the lower priced artists, it is interesting to see how HIGH their pricing can actually reach.  Rodney Demps is usually thought of as an artist with pricing at or  below $1,000, and up to perhaps $2,500 in an unusual case.  But the top hammer price for a Demps this year was $6,800.  It makes you realize that there are paintings out there that fill a quality range that is higher than what we typically think.

An Al Black hammered at $2,600, in an auction with a 24% buyers fee, resulting in a price paid of $3,225 …..  I’m sure this was higher than most people believed that an Al Black could sell for.

Note:   These are the high points for each artist in 2025.  In several cases, the high point for these artists was higher in 2024, or even earlier.  Prices in general, have not moved consistently with each artist, and in fact, as we will see further down, most artists saw their average prices decline in 2025.

Top 2025 Auction Painting For Each of the 26 Highwaymen Artists

In advance of looking at the individual artists, I thought it was interesting to also quickly evaluate which auction houses were producing the top prices.  They are as follows:

The surprise in looking at this is the good news that no auction house monopolizes the top paintings !!   The results are wide spread.  The number of top paintings were primarily sold at 3 auction houses, as indicated above. Manor wins the league table with 9 top paintings, but Manor should also be assessed on the basis of number of auctions and number of paintings sold, which are both far more than any other auction house.  Rennick was close behind with 7 top paintings, generated from less than half the number of paintings sold by Manor.   And the surprise is Florida Highwaymen, with 5 top paintings sold in only their first full year of business.

The top painting prices for each artist in 2025 are as follows:

Notes and Disclaimer:  … This was not as easy a list to put together as it may seem.  It is entirely possible that the list contains an error, or there is a higher priced, publicly sold painting that I missed.  If anyone does see an error in this chart, or blog in general, please get in touch with me so that I can fix it !

As mentioned, the list of highest prices per artist does not mean that there weren’t paintings sold at higher prices privately.  There are several artists for whom we have sold paintings for higher prices than those on the list here … most notably, Ellis Buckner, where I have sold 3 paintings in the last year that were each more than double the value of the Ellis Buckner top auction price.  Ellis Buckner did not have a single top quality painting come to auction in 2025.  His top quality paintings are rare, and rarely surface. I am sure there are also several other artists where private sales prices exceed this chart.  

In calculating the prices, with buyers fee’s, I used the posted buyers fee for each auction.  We all know that this may not be the final exact price because some auction houses give small discounts when not using a credit card to pay, etc. or they sometimes have special deals with buyers.  It’s impossible to determine these tiny variations.  T keep things consistent, I simply use the posted buyers fee.  What the chart does represent in general is a good snapshot of where the public auction market is, as these are the top 26 paintings from the more than 1,500 Highwaymen paintings sold at auction.  

A more detailed listing, including photos, dates, and sizes of each of the top paintings, may be found in the appendix at the end of this blog.

In Alphabetical Order,  By Artist:

Individual Artist 2025 Performance :

As discussed earlier, price trends for each of the 26 Highwaymen artists differed quite a bit. 

It is important to point out that average prices of paintings sold have a good amount of variability baked in – although artists who have large numbers of paintings sold are much less susceptible to this variability.  For example, it would seem that everyone knows that the prices for Sam Newton paintings have come down this year.  There were a large number of Sam Newton paintings sold, and the monthly statistics show the clear decline for the artist.  

At the same time, the average price for Alfonso Moran paintings have come down the most – almost 50%.  But everyone knows that there are very few sales of Moran paintings. Further, in 2024 the Moran paintings were all large, while in 2025 the paintings were generally much smaller.  With a very small pool of paintings being sold, the price decline does not reflect a true intrinsic decline, but rather, just a shift from large to small paintings from one year to the next.  This produced an exaggerated result due to the small number of data points.

The HiCo Index:

I have also analyzed what I refer to as our Highwaymen Collector (“HiCo”) index, which can be found in greater detail on our website:  www.TheHighwaymenCollector.com

The HiCo index is similar to something like the Dow Jones Average.  It looks at growth over an extended period of time.  In the case of the Highwaymen artists, our database starts with 2018.  Each Highwaymen artist starts with an index of 100 in 2018.  The website tracks the HiCo index for every artist on this basis.   If the HiCo index moves from 100 to 200, it means that the prices of paintings for that artist have doubled.  This report looks at the growth of the HiCo index from 2018 through the end of 2025.

First, a look at a simple alphabetical list for the 26 Highwaymen artists in the chart below.  .

An alphabetical chart does not say that much, other than the fact that there are clearly more artists with price declines (marked in red) for 2025, than price increases.  Anyone who has followed the market closely would not be surprised by this.  I have been writing in blogs since April that prices have been falling.  This has largely been a function of too many paintings coming into the market, during an economic cycle where consumers are heavily concerned with cost of living increases.

Looking at the price growth (or decline) for each artist, ranked from artists with the largest growth, to the lowest, the chart presents the following picture:

The top 5 artists defined by price increases in 2025, should come as no surprise. Everyone knows that demand for top-ranked Robert Butler (the artist with the largest value growth in 2025) paintings has been strong at every auction – even the weak auctions.  

I have been writing for 6 months that Rodney Demps (ranked #2) is having his moment, and is finally being sought after by more and more collectors.  The high quality Demps paintings have surged in value, while the more modest, common Demps paintings have exhibited less growth – but are also growing in value.

Average prices for 3rd ranked Al Black paintings have risen 25%, likely due to his passing this past spring.  Black was known for producing a large quantity of paintings, sold at low prices due to the high volume.  But that regular supply suddenly has dropped to zero, and it has pushed up his prices.  I would also note that prices for Black’s early upson paintings, as well as his paintings that were painted in prison, have increased sharply.

Finally, James Gibson and Ellis Buckner (ranked #4 and #5) round out the top 5 artists with the best price increases.  We have seen increased demand for later Gibson paintings, typically on canvas, while at the same time, early monochrome paintings are seeing a flat to declining market.  But the demand for quality later paintings by Gibson has pushed up the overall average.  Ellis Buckner has often been considered a lesser artist to his brother George, but the reality is that his paintings are just as good !  The market is catching up with this fact, and his prices are rising accordingly.

At the other end of the statistics, there are 11 artists whose average prices have declined by more than 10% in 2025.  A comment on each of these artists:

Mary Ann Carroll saw an 11% decline.  Her prices have been surging in recent years, and I regard this simply as a correction, as her prices have moved up too quickly.  As seen in the next chart, she has the 4th highest HICO score, meaning that since 2018, her prices were among the fastest growing consistently over the 7-year period.  This year was the year the market has corrected her rapid paced previous growth.

George Buckner declined by 12%.  When looking at the report on the website, it is clear that the decline in values came from upson paintings, while canvas paintings increased.  However, the overall decline of upson values exceeded that of the work on canvas.  Additionally, when many collectors now say they would like to purchase a Buckner, they are often indifferent between the two artists.  Ellis has been coming off a lower base of prices, so more interest was directed to his paintings, taking away some of the traditional preference and interest in George.

Sam Newton declined by 13%.  I was surprised that the decline was not larger, but we have seen in the last 2 months of the year some very strong and high prices for exceptional paintings by Sam Newton.  Fundamentally, the problem for the Sam Newton market is the flood of lower quality and average paintings being auctioned.  A single Elder dealer has been feeding Manor Auctions with an excessive number of these paintings, and after 10 consecutive months of the flood, the results are obvious.  Prices are falling fast due to over supply.  There is a limit to how many Sam Newtons can be bought by collectors every month. Eventually, the prices will move back up after the flood stops.

Willie Daniels has dropped by 15%.  This is the exact same explanation as above with Sam Newton.

Roy McLendon values declined 19%.  There is large quantity of paintings being offered, so the decline is real.  There are too many paintings coming into the market – and in particular,  too many late paintings of lower quality on canvas.

John Maynor declined by 20%.  In my view, simply a lack of interest.  The paintings coming to market were mostly generally dark, and not collector friendly.

The Hezekiah Baker decline (23%) comes as a surprise.  His paintings are generally always very good.  He is an early and core member of the Highwaymen, and most collectors I know are very positive about his work.  Looking at his pricing history over the last 7 years, there seems to be a distinct cyclicality to his prices.  They have strong growth for 2 years, and then fall back.  Then follow the same pattern again.  Baker’s prices grew strongly in both 2023 and 2024.  2025 was the correction year.

Sylvestor Wells, Carnell Smith, and Robert Lewis all saw overall declines in prices in excess of 25%.  There are no obvious reasons other than both Wells and Lewis saw a meaningful uptick of sales of small paintings (5×7, 8×10, etc) that clearly are selling at much lower prices than the 24×36 sized paintings.  This would pull their overall price average down, and is the reason the Highwaymen Collector website database divides paintings and average prices into size categories.

Finally, the largest drop of the year was Alfonso Moran with a price decline of 48%.  Given the small number of paintings sold from year to year (usually only 2 or 3), any change in the characteristic of the paintings being sold will have an outsized impact on an average price.  This year, the paintings sold were generally smaller, and of much lower quality, compared to the paintings sold last year.  Demand for Moran remains high – the only explanation for the lower prices are the small sizes of the most recent 2 paintings sold at Manor Auctions this year.  Both were small, and below average quality, while still bringing prices a touch above $10,000.   This compares with paintings by Moran in 2024 which all sold between $30-40,000.

Conclusion:  Year to Year Growth Statistics

Year to year comparisons certainly provide an indication of which artists have prices moving up, or not.  But as discussed, there are many variables that cloud the picture.

What is most interesting is to look at the growth results in 2025, simultaneous with looking at the growth results during the last 7 years.  The following chart is ranked in order of the 7-year growth HICO index.

Summarizing again… Every artist starts with a HICO number of 100 in 2018.  If their HICO score doubles to 200, that means their average price sold at auction has doubled.  Likewise, a HICO score of 300 means their average price has tripled, etc.

The chart above sorted by the HICO Index also has in its immediate left column the 2024/2025 growth percentage. Looking at the numbers together, we can easily see that the winning artist in terms of both the long term and current market growth, is Robert Butler.  Since 2018, Robert Butler’s prices have increased a total of almost 600 percent, and had growth in 2025 alone of 53%.    Only Willie Reagan and Charles Walker exceeded Butler’s 7-year growth numbers, but both of them had relatively stagnant growth during the last year.

Only 6 of the Highwaymen saw growth during the last 7 years of more than 300%, and even so, there were still quite dramatic differences.  They are:

Note that for these 6 artists, the compounded 7-year annual growth rate ranges from 31% down to 19%.  These are quite impressive numbers when compared to any investment alternative.  A 31%, or even 19% annual return over a period of 7 years, is not something that you will find anywhere else !

At the other end of the HiCo growth list, there are 8 artists, whose prices since 2018, have not reached the first key milestone of doubling in value.

It may come as no surprise that artists at the bottom of the growth list include Chico Wheeler and Robert Lewis, but most people would not have expected to see Alfred Hair and Ellis Buckner in this section of the list.

These numbers at the bottom of the list may not seem that impressive given the top performing artists, but the rates of return are indeed still very positive as indicated in the selected artists above.    The best  of this bottom group (Carnel Smith) still produced an annual compounded return of 9.85% – a number not easily achieved in most other investment categories.

The top performing artists like Charles Walker and Robert Butler produced compounded annual returns  of 31% and 29% respectively.

Disclaimer: All collectors know that the value of Highwaymen paintings has surged during the last 7 years.   However, the purpose of this report is NOT to provide investment advice !  Further, as security brokers always say… “past performance may not be consistent with future performance”.   And further still, collecting Highwaymen Art should not be put in the same category of investment decisions, like stocks and bonds.  We all like different artists for different reasons, and purchase decisions should be based primarily on perceived quality of the painting and your personal attraction to it – paintings should not be purchased on the basis of a financial investment analysis.

Looking to 2026.  Where would I focus ?

The Highwaymen market has evolved rapidly in the last few years.  It has also become flooded with what I call “commodity” paintings… average paintings that may be good quality, but do not stand out in any way.  Where would I look in 2026 ?  Certainly not “commodity paintings”.  I would focus on the artists who are the least common in the market, because their scarcity will always make them desirable. Focus on those artists whose prices are rising the fastest.   These paintings are not as easy to find, but the long term holding value has the best prospects . 

1. When looking at scarcity, beyond the obvious choices like Moran and Walker, I would also look at artists such as Willie Reagan and Curtis Arnett (each with fewer than 10 paintings offered at auction in 2025).  Additionally,  I would seek out the Buckners.   George and Ellis each had only 10-15 paintings offered in 2025, but they were largely poor to average quality.  These artists are always in high demand and low supply, making them highly attractive to add to your collection.
2. Of course if you are one of the few people in Florida who does not yet have a Sam Newton painting, by all means, buy one !  If you do have a painting, and are considering more, the area to concentrate with Sam Newton would be quality early upson pieces.  In addition, large paintings, ,,, 24×36 or larger.  The constant flood of Sam Newton paintings is primarily concentrated in small to medium sized paintings. The smaller selection of quality upson pieces, and large scale work, have both held up very well.
3. Robert Butler.  You can’t go wrong acquiring any painting, but paintings with animal life (deer, turkeys, cows, etc.) are always preferred.  Look for interesting frames, such as pecky cypress, to enhance value.
4. Charles Walker.  Later, detailed work on canvas are preferred. Walker paintings are almost as rare as Moran, but at a much lower price point.
5. Mary Ann Carroll.  Look for unusual scenes, or quality poincianas.  Everyone feels they must own a Mary Ann Carroll (as the only woman in the group), but an abundance of average quality paintings has recently softened prices for average paintings.  These may be a buying opportunity as Mary Ann Carroll has a unique, built-in demand that will always keep her prices strong.
6. Livingston Roberts and Roy McLendon.  At this time, look for early work on upson, and also larger scale paintings.  The high quantity of paintings coming to market recently has hurt prices of their average paintings.
7. Rodney Demps and Chico Wheeler are both regarded as non-mainstream Highwaymen artists. Their work has been overlooked for many years, and as a result, both were near the bottom of the value range for Highwaymen art.  That is changing fast – with both of them in the list of only 8 artists who had positive growth in prices during 2025.  Demps was ranked number 2 with 46% growth, while Chico squeaked in with just under 3% growth.  This is a dramatic statement for these 2 artists – compared to the 22 artists whose prices on average decreased in 2025.
8. Al Black will always be considered a core member of the Highwaymen, despite the fact that much of his body of work is not high quality.  His personality is legendary, and there are endless videos of him circulating everywhere on the web – keeping his interest level high.  His work done since approximately the year 2000, is in great abundance, and not the best.  It is often the entry point for a collector’s first painting because the work is inexpensive, and looks bold on the wall.  However, the paintings to focus on are his early paintings on upson board, and his prison paintings – painted in prison during his approximate 10 years of incarceration.  As the saying goes, in prison you have all the time in the world, and Al Black painted those paintings slowly and carefully.  These are his best paintings, and will be in the highest demand going forward.
9. James Gibson’s later paintings on canvas are growing rapidly in value.  On the other hand, the early monochromes have hit a plateau, only because there are endless examples in the market.  The monochromes are often quite attractive, but have limited potential for value growth due to the enormous quantity.   Focus on paintings with rich and detailed color. 
10. I could not discuss individual artists without mentioning Harold Newton and Alfred Hair.   The Harold Newton market has generally appeared to have peaked, or declined, unless the painting is a top 5-10% work in terms of quality.  The highest priced painting of the year was in fact a Harold Newton at over $50,000 with the buyer’s fee.  However, average quality paintings in the $5-8,000 range have suffered badly, often not even finding buyers and passing at auction.  While I have not done the statistics, my sense is that Harold Newton has had more paintings pass at auction than perhaps any other artist.  The market is being flooded with average paintings by the same “Elders” who are flooding the market with Sam Newtons.

     At the same time, the market for Alfred Hair paintings (again – top 5-10% work in terms of quality), is strong, but generally top out in the $10-12,000 range.  This is nowhere near the value of Harold Newton’s top work. The top Hair paintings are always unusual in their subject matter or scene represented.  Alfred Hair poinciana’s remain the most desirable subject due to their rarity.  The more common scenes have remained relatively flat in value in the $4-7,000 range. 

A final note about trends in the market … SMALL FORMAT.   It doesn’t matter who the artist is, demand for small format paintings is surging.  I define small format at 5×7, 8×10, 11×14, and other there-about sized paintings.  I exclude from this “Small” category 12×24 and 16×20, which are larger, effectively midsize,  and far more widely available.

As collecting of Highwaymen paintings has grown dramatically during the last 5 years, many collectors are finding that they have run out of room to hang more paintings !  The solution … small format paintings that can fill corners and be hung in places where a full sized painting cannot be considered.  The small size also makes for a very visual and  appealing mix with the larger paintings. People often describe them as jewels on the wall.  Prices have increased accordingly with 8×10 Mary Ann Carroll paintings routinely selling for $2,500-3,000, while the large 24×36 Mary Ann paintings are selling for $6-7,000.  Clearly, there is a very significant price premium being paid for the “jewels” of the Highwaymen world.  

Also fueling this trend is the fact that many collectors have embarked on a second collecting mission, … to find a small format painting by each of the Highwaymen artists.  I have never seen a Moran of this size, but I can only imagine that if one becomes available at auction, the price will explode beyond what seems reasonable.

Where will the market trends be in 2026? …  I believe more of the same trends we have seen in 2025.  

1. The “Elders” will continue flooding the market with Sam Newton, Harold Newton, and Willie Daniels paintings – keeping average paintings by these artists depressed in value.  
2. While demand is strong, I do not see growth in demand for Highwaymen paintings.  If the demand stays the same, and the number of paintings coming into the market continues to grow, average prices for average work will continue to fall.  This is why we have seen declines in average prices for 22 of the 26 artists in 2025.
3. “Top quality” will become more scarce, and more important.  This is where we will see price increases across all 26 artists.
4. The “Disrupters” in the market will continue to push new approaches to auctions and exhibitions, which will create more interest and excitement.  The annual exhibitions by the “Elders”, that look the same year-in and year-out, at this point do not advance the public appreciation and growth of the market. 
5. We may see another new, or even two new auction firms enter the fray. The key to success in the auction business is not the “selling” – but rather, the sourcing of paintings to sell.  They will compete on the basis of deals and fees to attract paintings, which will not advance prices, but ultimately be good for collectors if the competition results in lower fees, and better paintings being attracted to auction.
6. The number of dealer “Special Sales Events” is growing dramatically. What used to be a “Special Event” once every couple of months, is becoming an event almost every weekend. This is creating a “collector fatigue” in my opinion, which is not the best for the market, and will ultimately weaken prices further for the “commodity” paintings that are primarily sold in these new events.
7. An increase in fake paintings entering the market is creating a growing cloud over sales channels such as Ebay, and other on-line sources.  This will create greater focus on the quality distribution channels such as quality dealers and quality auctions. 
8. The “Legends of the Highway” movie has finally made it to your home screen, and  is a major accomplishment for the Highwaymen community.  Congratulations to all for this success !  However, my own personal opinion is that this movie will be great for expanding Highwaymen awareness in the state of Florida, but will NOT be a factor in increasing demand for Highwaymen paintings internationally or in the broader US market.  This “global” expansion has been a false claim by the “Elders” during the last two years as part of their effort to create an impression that the Highwaymen market will explosively grow because of the movie.
9. Finally, I believe we will continue seeing more and more  of the growing trend of “recycled paintings” coming to the auction market.  I have seen examples of hammered paintings reported as “sold”, when in fact they weren’t sold (and were bought by the auction house).  I have also seen examples of paintings that were sold in one auction house during the first half of the year, only to appear at auction again during the second half of the year.  This is another sign of an over-saturated market, which is not good for the average paintings, but again, will reinforce and generate more demand for the highest quality paintings.

We all know the 3 most important and well established criteria when evaluating real estate: location, location, and location.  The Highwaymen market is moving to the same philosophy with the 3 most important criteria:  quality, quality, and quality – with a side of scarcity when looking at Moran and Walker paintings !

With Best Wishes For A Successful Collecting Year In 2026 !

Mark Lerner

The Highwaymen Collector

786-599-5816

MJL@TheHIghwaymenCollector.com

Web: Https://www.TheHighwaymenCollector.com

Facebook:   The Florida Highwaymen Collector BUY/SELL/TRADE/DISCUS

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APPENDIX
2025 Highwaymen Top Auction Prices
(Alphabetic by Artist)

Notes about the paintings in this list:

• Interesting to point out that the record for 9 of the 26 artists included Poinciana’s!
• Prices listed here are hammer prices, with the buyers fee percentage represented below the hammer price.
• Sizes listed are of the work of art only and do not include the frames.
• If there were two paintings by the artist in 2025 with the same hammer price, I used the first painting sold (the earliest) as the record painting. The second painting merely tied the record.
• These records are for paintings auctioned in 2025. As mentioned in the report,there may be examples of paintings sold privately with higher prices, and there may also be paintings auctioned in 2024 (or earlier) with higher prices. This listing represents only the auction market of 2025.
• If I have missed a “record” painting, please let me know so that I can update the report.