Updated October 29, 2018 "Win-win" and "synergetic" are oft overused terms that rarely describe a business situation accurately. Most business circumstance boils down to a zero-sum-game, where one player's gain is another player's loss. That said, the relatively recent practice of auctioning new cars for charity appears to be a non-zero-sum-game where significant gains can be made by all concerned, and the biggest winners are those who need it most.

This article was originally catalysed in December, 2017, when McLaren sold one of its just-announced Senna road-registerable track cars for £2 million (US$2,685,460 excluding taxes) at a private auction. It has since been developed into the top 50 charity auction new car sales.

McLaren kept back one "build spot" of the hand-built, 500-units-only Senna and sprung an impromptu auction for that coveted remaining car on an unsuspecting annual gathering of the most devoted and passionate (and monied) McLaren enthusiasts.

For McLaren, the cost of the exercise is the build price of the Senna, which one assumes is considerably less than the £750,000 (US$1,004,662) which 499 customers paid for the privilege of buying a car with the name Senna on it. The much-loved Ayrton Senna is one of a handful of people with any legitimate claim on the title of the Greatest-Of-All-Time, and he's the only one in that group associated with just one marque. He might have driven the wheels off the Ralt, Toleman, Lotus and Williams cars he raced, but 35 of his 41 F1 wins and all three World Formula One Drivers Championships were achieved in a McLaren.

For that build price of say £500,000, McLaren got to donate £2 million to charity, and given a publicity machine as well-tuned as every other facet of a world's-best-practice company, it can leverage that donation into gold-plated corporate citizenship.

So McLaren wins, the Instituto Ayrton Senna gets a desperately-needed US$2,685,460 to promote its belief that "education is the key to a better world" in Brazil, and one person who really wanted a 789 hp, 1,198 kg McLaren Senna but didn't make the invitation list first time around, got their wish. Presumably, once his accountants have worked the charity angle at tax time, he'll win some more.

Scarcity driving value is the core principle of the laws of supply and demand, but on an even more granular level, cars that are limited editions, or the first or last of a species, also sell for more at auction, even five or six decades after they are new.

Hence, those same cars should be worth more when they are new, and it took the automotive community more than 100 years to recognize that fact because the first time we can find an example of VIN #001 being sold new at auction was the first Ford Shelby Cobra GT500 in January, 2006.

The announcement of the reprise of the Shelby Cobra GT500 in 2005 (that's the original and the final 2006 production model above) created such a stir in the performance car community, that Ford came up with the concept of auctioning off the first model off the line – VIN #001 – during Barrett-Jackson's televised Scottsdale 35th Anniversary auction in January, 2006, and donating the proceeds to the Carroll Shelby Children's Foundation.

It proved to be a master stroke in publicity terms, and a momentous occasion for the industry as both Edsel Ford and Carroll Shelby attended the Barrett-Jackson event and bidding went to $660,000 (including buyers fees), an unprecedented figure at the time.

From that point forward, Ford realized that selling VIN #001 cars on the auction block unlocked much latent value, that a donation of x (x = cost to manufacture the car) resulted in a contribution to charity of 5-10 times the retail value, and the goodwill, indeed the sheer GOOD generated by the event reflected well on everyone involved.

"Much like the Mustang ushered in a new era of competition between the automakers in the 1960s, Ford's use of our auction block to sell VIN 001 vehicles created a stir," says Steve Davis, president of Barrett-Jackson, reflecting on how Ford's initiative catalyzed a "corporate fight club."

"GM jumped into the fray with both feet, which compelled Chrysler to join the competition. Best of all, the cars were sold to benefit charity, so everyone truly wins."

Barrett-Jackson in particular needs to be commended for its never-ending contributions to charity. In the 47-year history of the auction company, it has now raised more than $94 million for charity and almost single-handed, it has manifested this marketplace.

At the same time that Barrett-Jackson was stirring the pot with the big three American car makers in 2006, a new charity in Florida was finding its feet.

The Naples Winter Wine Festival

There are tens of thousands of charities around the world, and they all support worthwhile causes but the Naples Winter Wine Festival truly deserves some credit for its organisational capacity, execution of the difficult with elegance and its sheer proactive nature.

The Naples Children & Education Foundation (NCEF) was established in 2001 with the vision of making a profound and sustaining difference in the lives of children in Collier County, Florida. The founders created the Naples Winter Wine Festival (NWWF) in order to meet NCEF's mission statement.

Within a three years of beginning the NWWF, it surpassed the iconic and long-standing Napa Valley Wine Festival as the dominant fundraiser in the country and was attracting vintners, chefs and entertainment personalities from across the world. It has been regularly fighting with Napa Valley Wine Festival for top place in Wine Spectator magazine's ranking of the most successful charity wine auctions ever since, with such extraordinary professionalism in every visible aspect of its performance that it is worth studying as a benchmark for excellence. Such eminence is not usually associated with charities and fundraising.

One of the many key facets of the NWWF, is that it didn't just sell donated wine, it went after delivering experiences that couldn't be otherwise accessed, and exclusive automobiles was one of those experiences.

When Rolls-Royce, Bentley, Lamborghini, Ferrari et al have limited edition cars, the size of their dedicated audience is so great that many esteemed individuals with a track record for purchasing a particular brand's new models miss the cut.

We're not quite sure how the NWWF managed to convince these established brands to part with key models, but for the last decade, the NWWF has been consistently delivering "the first available car" of many prestige brands and many significant models, then leveraging that value very effectively.

In a mature industry such as the automotive industry, it is worth noting that the Naples Winter Festival, a charity that is just 16 years old, has sold half the cars on the list below. That is a truly extraordinary performance, because doing it sustainably involves delivering the type of widespread positive publicity that those brands expect.

Corporate Citizenship

Good corporate citizenship is increasingly becoming an important factor in the annual report and this has become evident on the auction block where the additional value of milestone automotive models is being unlocked and retained for the benefit of charity, while significantly enhancing value to the donating company via advanced Public Relations.

The most expensive new cars sold at auction

The following list contains all new cars that have sold at auction for charity for more than US$400,000. As with many of the other lists we have constructed at New Atlas – such as the most expensive cars, the most expensive motorcycles, the most expensive movie cars, the most expensive guitars, the most expensive dresses, the most valuable scientific documents, and so on – we calculate all prices in United States dollars, based on exchange rates on the day of the sale.

This list has been developed over an eight month period, but even then, it may still be incomplete. So if you know of a new car that has sold at auction to the benefit of a charity for more than US$400,000, please email us at editor@newatlas.com with the details and we'll look into adding it to the list.

51 - 2015 Chevrolet Corvette Coupe

Price fetched: $400,000

Corporate Benefactor: Chevrolet | Date: September 26, 2014

50 - 2015 Mercedes SLS AMG GT Final Edition

Price fetched: $420,000

Corporate Benefactor: Mercedes-Benz | Date: January 24, 2015

49 - 2015 Lamborghini Huracán LP 610-4

Price fetched: $450,000

Corporate Benefactor: Lamborghini | Date: January 24, 2015

48 - Bentley Brooklands coupe

Price fetched: $450,000

Corporate Benefactor: Bentley | Date: January 26, 2008

The first Bentley Brooklands destined for the US market fetched $450,000. The Bentley Brooklands was a coupe version of the Bentley Arnage produced from 2008 to 2011 in limited numbers with traditional coach-building techniques.

47 - 2012 Mercedes-Benz SLS AMG Roadster

Price fetched: $450,000

Corporate Benefactor: Mercedes-Benz | Date: January 29, 2012

46 - 2017 McLaren 570 GT

Price fetched: $480,000

Corporate Benefactor: McLaren | Date: January 28, 2017

43 - 2014 Ford Shelby GT500 Convertible

Price fetched: $500,000

Corporate Benefactor: Ford | Date: August 10, 2013

Charity: Brain Injury Association of America

43 - 2016 Chevrolet Camaro SS

Price fetched: $500,000

Corporate Benefactor: Chevrolet | Date: September 26, 2014

43 - 2016 Chevrolet Corvette Racing C7.R

Price fetched: $500,000

Corporate Benefactor: Chevrolet | Date: September 26, 2015

42 - 2019 Bentley Continental GT

Price fetched: $520,000

Corporate Benefactor: Bentley | Date: January 27, 2018

41 - 2016 Ford Focus RS

Price fetched: $550,000

Corporate Benefactor: Ford | Date: January 30, 2016

Charity: JDRF

40 - 2015 Land Rover Defender 90

Price fetched: $596,482 (GBP£400,000)

Corporate Benefactor: Land Rover | Date: December 16, 2015

Land Rover made quite an effort to celebrate the two-millionth Land Rover being manufactured in May 2015. Production of the iconic Land Rover had begun at the Solihull plant in 1948 and most landmark vehicles produced there (such as the millionth car) had been retained for the company museum.

The auction car was given a bespoke design by Land Rover's Special Vehicle Operations team, and an all-star cast of 33 notables and brand ambassadors built the vehicle, including Bear Grylls, Virginia McKenna OBE and Stephen and Nick Wilks, sons of the founders of Land Rover. All proceeds went to IFRC, which will use the donation to help communities in South-East Nepal to improve how they tackle natural disasters, and the Born Free Foundation which plans to use the funds to support the "Project Lion Rover" wildlife conservation initiative in Meru National Park, Kenya.

37 - 2014 Chevrolet Camaro Z/28 2-Door

Price fetched: $650,000

Corporate Benefactor: Chevrolet | Date: January 18, 2014

37 - 2016 Ferrari F88 Spyder

Price fetched: $650,000

Corporate Benefactor: Ferrari | Date: January 30, 2016

37 - 2018 McLaren 720S by McLaren Special Operations

Price fetched: $650,000

Corporate Benefactor: McLaren | Date: January 27, 2018

36 - 2007 Ford Shelby GT500 Fastback

Price fetched: $660,000

Corporate Benefactor: Ford | Date: January 22, 2006

One of the primary catalysts that kicked off this goodwill marketplace, the auction of the first Ford Shelby GT500 Fastback convinced Ford of the viability of leveraging its VIN #001 cars on Barrett-Jackson's televised auctions for the benefit of all, and Ford's initiative saw the other members of the big three follow suit.

33 - 2014 Chevrolet Camaro COPO

Price fetched: $700,000

Corporate Benefactor: Chevrolet | Date: January 17, 2014

33 - 2016 Ford Shelby GT350

Price fetched: $700,000

Corporate Benefactor: Ford / George W Bush | Date: August 16, 2015

33 - 2015 BMW M5

Price fetched: $700,000

Corporate Benefactor: BMW | Date: January 15, 2015

32 - 2007 Ferrari FF

Price fetched: $710,000 (approximate)

Corporate Benefactor: Ferrari | Date: July 3, 2011

Venue: Italian Embassy, Tokyo

Charity: For the benefit of victims of the 2011 Japanese earthquake

31 - 2014 Rolls-Royce Wraith

Price fetched: $750,000

Corporate Benefactor: Rolls-Royce | Date: January 25, 2014

30 - 2013 Ferrari F12 Berlinetta

Price fetched: $750,000

Corporate Benefactor: Ferrari | Date: Jan 26, 2013

29 - Rolls-Royce Dawn

Price fetched: $750,000

Corporate Benefactor: Rolls-Royce | Date: January 30, 2016

28 - Rolls-Royce Phantom VIII

Price fetched: $780,000

Corporate Benefactor: Rolls-Royce, Robb Report, Alpha Omega Winery

Date: January 27, 2018

0 - 2007 Maserati Quattroporte

Price fetched: $790,000 – achieved with a $5,000-a-ticket, 200 ticket raffle so it doesn't qualify as an auction, but we've included it in the list without an official number as an inspiration for the various ways a charity can extract value from a high priced automotive donation.

Corporate Benefactor: Maserati | Date: January 27, 2007

The Maserati Quattroporte was custom-made for the Naples Winter Wine Festival and was finished in "Deep Bordeaux" with twenty-inch ball-polished wheels, carpets and stitching in Bordeaux and customized door moldings, which read "Naples Winter Wine Festival 1 of 1."

26 - 2015 Chevrolet Corvette Z06 Convertible

Price fetched: $800,000

Corporate Benefactor: Chevrolet | Date: January 16, 2015

Charity: United Way

26 - 2005 Rolls-Royce Phantom

Price fetched: $800,000

Corporate Benefactor: Rolls-Royce | Date: February 5, 2005

23 - 2004 Ford Shelby Cobra Concept Car

Price fetched: $825,000

Corporate Benefactor: Ford | Date: November 5, 2017

Venue: GAA Classic Cars Auction, Greensboro, North Carolina

Charity: the restoration of Fair Lane, the 1915 estate of Henry and Clara Ford in Dearborn, Michigan

23 - BMW i8 Concours d'Elegance Edition

Price fetched: $825,000

Corporate Benefactor: BMW | Date: August 16, 2014

23 - 2015 Dodge Challenger SRT HEMI Hellcat

Price fetched: $825,000

Corporate Benefactor: Dodge | Date: September 27, 2014

Las Vegas icons Wayne Newton and Penn Jillette (of Penn & Teller) were on the Barrett-Jackson auction block to encourage bidding for this 2015 Dodge Challenger SRT Hellcat VIN 001.

22 - 2017 Mercedes-AMG GT3 'Laureus'

Price fetched: $885,000

Corporate Benefactor: XXXX | Date: XXXX , 201X

Venue: RM-Sotheby's | Monterey, 2018

Charity: Laureus

21 - 50th Anniversary Limited Edition Lamborghini Aventador

Price fetched: $900,000

Corporate Benefactor: Lamborghini | Date: January 25, 2014

Number #45 of 100 made, this 50th Anniversary Limited Edition Lamborghini Aventador, sold for $900,000 along with access to the inaugural US event for the Lamborghini Experienza program. Only 20 of these rare cars were available in the United States.

20 - Ferrari 458 Speciale Aperta

Price fetched: $900,000

Corporate Benefactor: Ferrari | Date: October 12, 2014

Venue: Ferrari 60th anniversary in the United States Celebrations

Charity: Daybreak

Auctioneer Charlie Ross brought the guests at Beverly Hills City Hall to their feet as he auctioned the first of 499 examples of the Ferrari 458 Speciale A. The car wore VIN #001.

19 - 2019 Chevrolet Corvette ZR1

Price fetched: $925,000

Corporate Benefactor: Chevrolet | Date: January 21, 2018

Venue: Barrett-Jackson | Scottsdale, Arizona

18 - 2011 Ferrari 458 Italia

Price fetched: $950,000

Corporate Benefactor: Ferrari | Date: January 29, 2011

17 - 2018 Lamborghini Huracán RWD Coupé

Price fetched: $966,775 (€809,375)

Corporate Benefactor: Lamborghini | Date: May 12, 2018

Venue: RM-Sotheby's | Monaco

Charity: Vatican Charity Fund

13 - GT350R Ford Shelby

Price fetched: $1,000,000

Corporate Benefactor: Ford | Date: January 17, 2015

Charity: JDRF

VIN 001 of the new GT350R Ford Shelby with flat-plane crankshaft, the most powerful naturally aspirated engine Ford had produced to that time.

13 - 2014 Corvette Stingray Convertible

Price fetched: $1,000,000

Corporate Benefactor: Chevrolet | Date: April 5, 2013

The first of the all-new 2014 Corvette Stingray convertibles and another approximate 10-1 ratio from the retail to auction price.

13 - 2015 Chevrolet Corvette Z06 Coupe

Price fetched: $1,000,000

Corporate Benefactor: Chevrolet | Date: April 12, 2014

This 2015 Corvette Z06 was the first retail production vehicle available of the all-new, next generation Corvette Z06. As many road testers are quick to tell you, you'll need to head towards a million bucks to get equivalent performance to the $100,000 Corvette ... well someone believed them. That someone was Rick Hendrick, NASCAR team owner and Hall of Fame member. Hendrick has purchased three of the cars on this list.

13 - 2009 Chevrolet Corvette ZR-1 Coupe

Price fetched: $1,000,000

Corporate Benefactor: Chevrolet | Date: January 19, 2008

The "First Retailable Unit Built" Corvette ZR1 went to auction at Barrett-Jackson Scottsdale on Saturday, January 19, 2008, fetching $1 million. Given that a hamburger-with-the-lot ZR1 cost $105,000 when they went on sale, that's another remarkable price multiple approaching x10.

0 - The Stinger

Price fetched: $1,034,000

Corporate Benefactor: Window World Cares | Date: May 24, 2016

While this is more a novelty than a new car, we included it in the list without an official position because it fits the spirit of the endeavor, if not the exact definition. It's a Honda Indy car of recent origin, painted in the colors of the 1911 Marmon Wasp that won the inaugural Indianapolis 500. At last count, the car has been signed by 249 of the 273 living Indianapolis 500 Veterans.

12 - 2014 Chevrolet Corvette Stingray Coupe

Price fetched: $1,100,000

Corporate Benefactor: Chevrolet | Date: January 19, 2013

The first example of the seventh generation Corvette went to the auction block with a following of biblical proportions, driving one of the greatest new-price-to-auction-price ratios we can find. A fully optioned Stingray maxes out at $73,360, and the winning bidder for this 2014 Corvette Stingray VIN #0001 paid $1.1 million – that's a "feel good ratio" of 15-to-one.

11 - 2017 Acura NSX

Price fetched: $1,200,000

Corporate Benefactor: Acura (Honda) | Date: January 29, 2016

Honda took a long time in developing the second version of the NSX. You can read all the ins and outs in our coverage of the NSX world premiere, subsequently released details and even more details, and finally, even more details.

As a quick recap, the NSX features a 573-hp (427 kW) hybrid drive with twin-turbo 3.5-liter V6 engine, three electric motors and a nine-speed transmission. The mid-mounted V6 powers the rear wheels with help from the direct drive rear motor, and the other two electric motors power the front wheels. With this layout, the NSX is able to deliver instantaneous torque during acceleration and better control in the twists.

As part of one of the longest pre-release sagas in automotive history, the first production NSX was auctioned by Barrett-Jackson and sold for $1.2 million, approximately six times the fully optioned price of $207,500. The Acura NSX is also the first American designed and built car on this list.

10 - 2005 Ferrari Enzo

Price fetched: $1,282,987

Corporate Benefactor: Ferrari | Date: June 28, 2005

Venue: Sotheby's Ferrari Maranello Auction

Charity: Caritas

This car was the 400th and final Ferrari Enzo and was originally given to His Holiness Pope John Paul II by Ferrari. The Pope asked that it be sold and the proceeds donated to charity, which was done at Sotheby's single-marque Ferrari sale conducted at Maranello, Italy in June, 2005.

The car subsequently became part of the famed Pinnacle Collection which sold at RM-Sotheby's Monterey Sale in August 2015. A decade after it first sold for $1.28 million, the final Enzo fetched $6,050,000.

9 - 2007 Bentley Continental GTC Convertible

Price fetched: $1,300,000

Corporate Benefactor: Bentley | Date: January 27, 2007

The GTC in the Bentley Continental GTC stands for "Grand Touring Convertible" and in 2007, the Naples Wine Festival auctioned the first GTC available in America ahead of overwhelming demand and a limited build schedule for the $200,000 2+2 convertible. As usual at the Ritz Carlton Golf Resort during the Naples Winter Wine Festival, there was enough interest in being the first on the block with the latest toy to drive bidding to more than six times the normal buy price.

8 - 2018 Chevrolet Corvette Carbon 65 Edition

Price fetched: $1,400,000

Corporate Benefactor: Chevrolet | Date: January 21, 2018

Venue: Barrett-Jackson | Scottsdale, Arizona

Charity: George W. Bush Presidential Center's Military Service Initiative

7 - 2017 Mercedes-Maybach G650 Landaulet

Price fetched: $1,407,875 (€1,200,000)

Corporate Benefactor: Mercedes-Benz | Date: October 6, 2017

Venue: Bonhams Zoute Sale, Belgium

The limited-edition Maybach G650 Landaulet inspired our own Scott Collie to pen an article entitled Off-road absurdity, thy name is Maybach G650 Landaulet. The luxury mastodon is a car of preposterous specification, with a 630 hp AMG V12 biturbo engine, a curb weight of 7,300 pounds, a length of more than five meters, a height of two meters, half a meter of ground clearance, and four wheels sharing responsibility for distributing 1,000 Nm of torque.

Despite a price of €630,000, it sold out inside a week, with one held back by Mercedes-Benz, and auctioned by Bonhams during the Zoute Grand Prix in Knokke, Belgium to the benefit of the Laureus Sport for Good Foundation. More detail.

6 - 2012 Ferrari 599X