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Checkered Flags and Checkbooks: Classic Race Cars Are Hotter Than Ever at Monterey Car Week

red car parked on street
Classic Race Cars’ Values Explode at Car WeekBrian Henniker/Gooding & Company

Old race cars used to be treated like old racehorses: put out to pasture, or worse.

Those glue-factory days are over. Monterey Car Week features a stable of racing thoroughbreds up for auction—or nibbling on fairway lawns, like Jaguar’s sui generis 1954 D-type prototype. Cars you can (mostly) never drive on street, yet still worth six, seven, even eight figures to the right buyer.

Sal Castello will have a front-row seat to this reversal in fortune at Friday’s Gooding & Company auction. Castello remembers his late father, Joe, pulling up at their home in San Jose with a 1956 Ferrari 500 TR on the back of a Chevy flatbed. Sal was eight years old when his father, a gunsmith and machinist, bought Ferrari’s first Testa Rossa model. Castello hesitates briefly before revealing what his late father—a first-generation Italian American who didn’t like to waste money—finally paid for the Ferrari he’d been coveting: $1500.

steering wheel of a red car
1956 Ferrari 500 TRBrian Henniker/Gooding & Company

“At the time, it was just an old race car, and nobody wanted that shit,” Castello says. “It was outdated. Most of the guys who bought those cars would put a 350 Chevy in it and go have fun.”

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The swoopy Scaglietti Spider had earned class wins at the 12 Hours of Reims, the Bahamas Speed Weeks, and the Cuban Grand Prix and was driven by big names at the 24 Hours of Le Mans and other events. But in San Jose in 1968, the Ferrari was an obscurity, its Lampredi 2.0-liter four-cylinder engine unexpectedly in boxes when Joe Castello went to bring the car home.

Sal remembers his father using the Testa Rossa’s engine block as a footstool at his shop. His next Ferrari, a 275 GTS, became Joe’s daily driver. Finally, in the mid-Eighties, Castello Sr. and his mechanically gifted friends built a rotisserie and restored the red 500 TR, uncovering hidden layers of blue and white paint and other race liveries. Sal was the gopher and assistant.

car engine
1956 Ferrari 500 TRBrian Henniker/Gooding & Company

“They were renaissance guys. They drew out and thought out and built everything themselves,” Sal Castello recalls. “When it came to final assembly, I made every freaking gasket of that engine, cutting them for weeks.”

After six years of rebuilding, the Castellos showed the 500 TR at Pebble Beach in 1991 and Monterey’s Concorso Italiano. Satisfied with their DIY work, the family hasn’t shown the car in public for 30 years.

Now it’s safe to say this race car will never be overlooked again: The 500 TR, one of just 17 made in 1956, is expected to fetch $4 million to $5 million at auction.

“It’s an awesome car,” Castello says. “I love the damn thing. I hate to part with it, but it’s time.”

red car seats
1956 Ferrari 500 TRBrian Henniker/Gooding & Company

Sitting Still or Going Fast

Despite getting a brighter spotlight, race cars make up a small percentage of classic-car sales. The collector-car insurer Hagerty expects racers to make up about 0.5 percent of the roughly 12,000 cars headed to auction stages this weekend. That would be just 60 cars for a niche of bidders to tussle over.

Buyers tend to fall into two overlapping categories with different priorities: People who want to preserve a piece of history—the investment upside doesn’t hurt—and people who want to drive (or recruit hired guns) at the Rolex Reunion and other vintage events or series.

the rolex monterey motorsports reunion
Watching these classics roar around Laguna Seca at the Rolex Monterey Motorsports Reunion is a Car Week necessity.Rolex

The second group “cares more about performance specs, how competitive a car is going to be on track, and how race-ready it is,” says Brian Rabold, vice president of automotive intelligence for Hagerty.

For preservationists, experts cite key drivers of value: A specific documented race history, including who drove the car, where it raced, and how high it finished. Condition, originality, and provenance are huge.

David Brynan, senior specialist at Gooding & Company, says more and more of the rarest racers are being tucked away.

“The really historic cars aren’t being raced as much, so they’re becoming museum pieces and collector cars,” Brynan says.

white racecar in front of garage
1976 Porsche 935Mathieu Heurtault/Gooding & Company

Brynan points to a heart-skipping 1976 Porsche 935 on offer, in Martini Racing livery. It’s merely the first 935 ever built. A car that Jochen Mass, at the time, described to Road & Track as fast enough to catch and pass F1 cars on the straights. The auctioneer pegs an estimate at $4.5 million to $5.5 million.

“I doubt that car will be raced competitively,” Brynan says of the Porsche. “The historical significance and special nature of the car takes it to a different category of collectible.... Here’s a factory team car that won Watkins Glen and helped Porsche win the Group 5 championship. Now it’s been restored, with Martini livery, and is basically perfect. It’s a car that checks all the boxes.”

white racecar detail
1976 Porsche 935Mathieu Heurtault/Gooding & Company

Yet vintage racing is going gangbusters, and new series and racing opportunities are stirring a changing of the guard. At the high end, newer sports prototypes and GT cars are red-hot. They come across as faster, more advanced, and, importantly, safer than dicier postwar models that boomers long favored. Examples include a spectacular 1995 Ferrari 333 SP Evoluzione that may fetch $6 million to $8 million at Gooding. Together with Dallara, Ferrari built 40 models for privateers in its return to sports racing after a long hiatus. This particular cream puff was fast enough to score sixth overall at the 1997 24 Hours of Le Mans. Over at Hagerty’s Broad Arrow sale, a 1997 Porsche GT1 Rennversion that won an IMSA championship may draw bids of $8.5 million to $10.5 million. Just your typical track-day cars, right? That Porsche estimate is more than double what Gooding expects for its 1934 Duesenberg Model J disappearing-top convertible, among the all-time prewar classics.

“When those cars were five or six years old, there wasn’t much you could do with them,” Brynan says of these Nineties IMSA competitors. “Now there’s lots of active racing and events for those cars that drives interest and values.”

Brynan cites another sweet spot in the market for dual-purpose classics that were street-legal racers but relatively uncomplicated to operate: anything from old Alfa Romeos and Porsche Spyders to the Ferrari 250 GTO.

The trick, however, is to find original cars “that survived without too much drama during years of being obsolete and not collectible,” Brynan says.

Generally, the older the car, the more it morphed and modified into different forms. Sports racers of the Fifties often lived a second life as weekend cars, many with replacement American V-8s under the hood. Like washed-up movie stars, some now-fabled race cars fell to unseemly depths.

black car parked on racetrack
1959 Masterati Tipo 61 BirdcageGooding & Company

Weekend sales include a 1959 Maserati Tipo 61 Birdcage that was raced through 1963. By 1965, its owner was ready to take $2300 for a car Gooding now expects will hammer for $5 million to $6 million. A Porsche 550 Spyder on auction was running Le Mans and the Nürburgring in 1957. Three years later, it was languishing on a used-car lot in Culver City. Its buyer yanked out its original four-cam Carrera engine and replaced it with a 1500 Super pushrod motor.

The next owner drove it as a weekend car for 22 years. A Porsche specialist finally restored the car in the Eighties and won in its first-ever outing at the Monterey Historic Automobile Races. At Porsche’s 50th-anniversary celebration at Pebble, the Spyder won its historic race group and took the Road & Track Trophy at the Concours d’Elegance to boot.

“Cars from that period tend to have more complicated lives,” Brynan says, with some understatement.

Now the silvery Spyder has gone from a used-car lot to an estimated $3.5 million to $4.2 million sale, enough to make James Dean roll over in his Little Bastard’s grave. (What, too soon?)

The 1965 Ford GT40 Mark I already seemed obsolete and unloved in its own time, as improved Mark II models swept Le Mans in a Ford v. Ferrari ’66. And that seminal GT40 was doornail dead after the big-block Mark IV torched Le Mans with Dan Gurney and A.J. Foyt in ’67. But John Wyer revived the original in Lightweight guise, with fabled Gulf livery and aluminum cylinder heads squeezing 440 hp from a modest 302-cid V-8—and squeezed a final pair of Le Mans wins in ’68 and ’69.

Mecum is dangling one of 10 GT40 Lightweights at auction. It weighs in at about 2000 pounds—perhaps less than the weight of cash it will take to buy it.

white racecar on track
1969 Ford GT40 LightweightMecum Auctions

On Sunday, Jaguar will plop its D-type onto the 17th fairway during the Concours d’Elegance. It’s the prototype of the Malcolm Sayer racer that went straight to Le Mans upon completion, breezed to 170 mph during testing, and broke the lap record by five seconds. It promptly won Le Mans. Did I mention the Jaguar is not for sale? But this being Pebble Beach, you’re welcome to stroll up and make an offer.

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