Estimate: Unknown
RM Sotheby’s
Any narrow-body Cobra is a special and extremely valuable thing, but this particular example may well be verging on priceless. Bought new by Henry “Hank” Williams (not that Hank Williams, but he was a jazz drummer who played with B.B. King and Ray Charles), this car was a regular at many a Shelby gathering, owned for nearly six decades by a man who would become a close personal friend of Carroll Shelby. Williams drove his Cobra 140,000 miles over his lifetime, covering the last of those miles one year before his death at the ripe old age of 99. He raced it in nearly 400 races, entered it in countless shows, and was the first Black person to drive a sports car for a lap of the Indianapolis Motor Speedway in it. The car is being sold by his family trust, and few cars come with a better story.

Estimate: $4.5 million–$5 million
Gooding & Company
In the year that Porsche celebrates 50 years of its roadgoing 911 Turbo, the ultimate turbocharged racing derivative of the 911 should fetch big money. Powered by a 2.9-liter flat-six boosted to almost 600 horsepower in racing trim, the 935 was so fast in a straight line that it reeled in F1 cars of the day when tested on the same track. Further, this isn’t just any 935, but the very first one ever built, chassis 001. It’s the only ex-works 935 in private ownership (its sister car has been in the Porsche Museum for 48 years) and is incredibly special as the embodiment of Porsche’s turbocharging heritage.

Estimate: $5 million–$7 million
RM Sotheby’s
Luigi Chinetti’s North American Racing Team (NART) was arguably the most important Ferrari-backed privateer team, and its racing successes were a large part of making the prancing stallion well regarded in the U.S. market especially. This 275GTB/4 was a big part of that success, as it won its class at the grueling 1969 24 Hours of Daytona, with Ricardo Rodriguez and racing journalist Sam Posey at the wheel. One of the extremely rare alloy-bodied cars, this 275GTB/4 started out as a luxurious road car but was retrofitted for racing duties. It comes with Ferrari certification of its originality and has been faithfully returned to its winning Daytona racing specification.

Estimate: $6 million–$8 million
Gooding & Company
Ferrari’s long absence from sports-car racing was broken in the mid-1990s by the 333 SP, which was basically a Formula 1 engine wrapped in carbon-fiber endurance racer bodywork. One of nine chassis built by Dallara, this example was campaigned successfully by the Scandia and Moretti racing teams, the latter of the famous Momo steering-wheel brand. It’s a monster, with a 4.0-liter V-12 screaming toward an 11,500-rpm redline, and a racing pedigree everywhere from Pikes Peak to Sebring to Le Mans. A very successful prototype racer in its day, it’s eligible for vintage endurance racing events, including Ferrari’s own exclusive F1 Clienti program.

Estimate: $6 million–$8 million
Gooding & Company
This Ferrari battled Jaguars and Mercedes-Benzes in its day, but it also had to survive the indignity of having a Corvette engine swapped in and later being bought and painted yellow by pop artist Andy Warhol. Yet survive it did, luckily being reunited with its original 3.5-liter four-cylinder engine by David Cottingham of DK Engineering. One of the U.K.’s best Ferrari specialists, DK carefully refurbished it to original specification, and it made its debut at the Goodwood Revival in 2011. With extensive racing provenance, this four-cylinder Ferrari is just as important as its V-12 cousins. Among its wins were two podium finishes in California with none other than Carroll Shelby at the wheel.

Estimate: $8 million–$10 million
RM Sotheby’s
A modern hero among a treasure trove of classic Ferraris, this racing machine hails from F1’s era of howling V-10s and lantern-jawed German dominance. Driven to three podium victories by Michael Schumacher en route to his 2002 World Championship victory, this car completed a total of nearly 400 faithful laps in service of Scuderia Ferrari, right in the middle of one of its most successful periods. There are only a handful of Schumacher-driven F1 cars in private hands, so this is a rare chance to drive what one of the greats did during his golden era. You might want to budget for some driving lessons, though.

Estimate: $9 million–$11 million
RM Sotheby’s
One of what must be the most pedigreed hot rods of them all, this 625 TRC Spider was raced in-period to over 20 podium finishes. It was originally fitted with an enlarged version of the “Testa Rossa” four-cylinder engine (so named for the red crackle finish on its cylinder head). That 2.5-liter four-cylinder engine, numbers-matching of course, does come with the car, but this TRC is currently powered by a 3.0-liter Ferrari V-12. Which is as it should be. The 625 TRC was basically the four-cylinder prologue to the V-12–powered 250 Testa Rossa, so with this car you get the best of both worlds: take it to the racetrack and drive the wheels off it, or fit the original engine and display it at a concours event.

Estimate: $9 million–$11 million
Gooding & Company
Completed in September 1937 at Bugatti’s factory in Molsheim, France, this Type 57SC Atalante was originally delivered to London, even as war clouds gathered in Europe. Only 17 Atalantes were made, sister cars to the perhaps more famous 57SC Atlantic, equally capable of high performance but with a single-piece windshield and without the Rocketeer rear fin. This example was recently restored to its original London delivery specification and has been certified to have its original chassis, engine, and coachwork. It won its class at Pebble just last year, and should thus fetch top dollar as an example of prewar Bugatti excellence.

Estimate: $15 million+
RM Sotheby’s
Equipped with Ferrari’s largest engine at the time of its construction, a 5.0-liter V-12, just four examples of the 410 S were built, intended to compete in Mexico’s Carrera Panamericana. None ever did, as the race was canceled. This one made its way to California via an Italian-born racing enthusiast, where it was later driven by Carroll Shelby to victory in the Palm Springs Road Races in 1956. This car would eventually make its way to Mexico, first when its owner fled the U.S. to avoid tax issues, later passing into the hands of a Mexico City–based owner who raced it in the mid-1960s. Properly restored, it was shown at the Pebble Beach Concours in 2018 and is ready to race again in vintage events.

Estimate: $15 million–$17 million
Gooding & Company
In terms of the most valuable collector cars, a Ferrari 250 is basically the equivalent of a Leonardo da Vinci painting. It’s an obvious choice, but then the appeal is obvious, especially with the ripping exhaust note of a 3.0-liter Colombo V-12 filling your ears as warm California sunshine floods into the cabin. This example has been certified as original and numbers-matching by Ferrari’s Classiche Department and is thus about as blue chip an investment as you can get. It is so choice; if you have the means, I highly recommend picking one up.

Estimate: $16 million–$18 million
RM Sotheby’s
Second of two similar cars coming to this year’s auction, this numbers-matching short-wheelbase California Spider is actually the first of the 56 examples made, making it even more significant in terms of Ferrari history. Of particular note, it left the factory as just one of perhaps three California Spiders with a competition-spec engine. More than rolling art to be tucked away in a collection, a California Spider is a car meant to be driven. The previous owner of this one took it everywhere from Le Mans to the Nürburgring, and we hope the next owner continues the tradition of actually driving such a machine.

Estimate: $16 million–$20 million
Gooding & Company
Perhaps the next best thing to winning a trophy at the Pebble Beach Concours d’Elegance is purchasing a former winner. This Alfa Romeo 8C 2900B would be special enough by itself, as it is drop-dead gorgeous with a ferocious twin-supercharged straight-eight engine, but it also has the provenance of being awarded Best in Class at Pebble in 2000. The 2900B was basically untouchable in performance when new, with power to match those graceful looks. These cars are in huge demand yet rarely become available, as many collectors consider them the Holy Grail of Alfa Romeo road cars. This Lungo Spider is just one of five thought to survive, and it has an exciting pedigree, having spent its early years in Egypt and more recently having been recovered after a daring heist. It’s a jewel of a car with a great backstory and will doubtless be the belle of the Monterey auctions.