Wheels of Fortune: Inside Concours d'Elegance

On the 18th fairway above the sea at Pebble Beach, the world's most prestigious car show presides. Writer Jacob Baynham goes inside the spectacle and the collectors' sport of the Concours d'Elegance.

A quarter moon still hangs above Stillwater Cove when Ron Elenbaas, an automobile collector from Key Largo, Florida, crawls out of bed and sneaks out to his car. It's not yet 4 a.m., and Elenbaas doesn't dare start it for fear of rousing his competitors. Instead he silently pushes it onto the asphalt, around a corner, and into position at the edge of the 18th fairway on California's Pebble Beach Golf Links. He's first in line, a small victory that makes him grin.

"Everything's a race," he confides. "Everything."

Even in the darkness, Elenbaas's car is distinctly beautiful. It's a rare 1910 American Underslung, smartly restored with polished brass headlamps, black stenciling over a white body, and 42-inch hickory wheels. It looks like a sports car from the stagecoach era. Elenbaas bought it 10 years ago and had it professionally refurbished. Only 300 Underslungs were built in 1910. To the best of Elenbaas's knowledge, his is one of two that remain.

Before long, a pale green 1954 Alfa Romeo Zagato coupe roars down the road and pulls in behind Elenbaas. Two Italians climb out. One of them recovered the car from a garage in Rome, where it had sat for 40 years. He got it running and sent it here by ship. Another engine breaks the stillness, and Elenbaas watches a feather-white 1958 BMW 503 cabriolet coast out of the gloaming toward the Italians. "This guy thinks he's going to be first," Elenbaas says, "and he's going to be third."

One by one, 208 cars and eight motorcycles stack up behind Elenbaas like actors assembling in the wings. Together, they comprise a 78-year cross-section of automotive glamour, from an 1892 steam-powered Philion Road Carriage to a 1970 Rolls-Royce Phantom VI built for Queen Elizabeth's tour of Australia. The owners mingle on the pavement.

When dawn finally breaks, like a sheet swept from a concept car, the drivers rumble onto the green in clouds of exhaust. The early light chromes the Pacific behind them. Elenbaas was first in line, but now the real competition begins—the 64th annual Pebble Beach Concours d'Elegance.

The Concours was born on California's Monterey Peninsula in 1950, when a group of car enthusiasts organized a European-style road race through the Del Monte forest and then displayed the cars at Pebble Beach. The idea has since grown into a week of races, auctions, and exhibits held each August, when revving engines drown out the murmur of the waves in the sleepy village of Carmel. This Concours, sometimes called the Academy Awards of automobiles, is the headline event.

At auctions before the show, rare cars fetch vast sums. This year a Ferrari 250 GTO went for a record $38 million. Only a select, opulent few have the passion and the money to afford this hobby. Ralph Lauren is a two-time Concours winner. Jay Leno, who owns more than 200 unusual cars and motorcycles, is an annual guest.

On the turf, Lisa Schigiel surveys the rows of automobiles from the front seat of her 1952 Cisitalia 202 convertible. "This show is basically an art gallery on wheels," she swoons. The exhaust has given way to cigar smoke as the owners celebrate the occasion. This year the cars are entered among 27 classes, with titles such as Postwar Touring and Prewar Preservation. Every car has a story—its "provenance," in collectors' parlance. One 1923 Rolls-Royce Silver Ghost was owned by a Prohibition-era bootlegger and still bears a bullet hole from a rum deal gone bad. Another Rolls has appeared in Downton Abbey. Nearby is a 1936 Horch 853 cabriolet that belonged to a German general during the war before an Allied officer confiscated it at gunpoint. A 1929 Model J Duesenberg was first owned by the lawyer who settled Charlie Chaplin's divorce. Down the fairway is the sleek, bubble-capsuled Jaguar XK120 in which Norman Dewis set the world speed record—172.4 miles per hour—in 1953. (Dewis, now 94, is here, too.)

Judging begins soon after the cars are parked. At 10:30 a.m., the gates will open to the public (at $300 a ticket), so the judges hurry to scrutinize the cars while there's room. Dressed in navy blazers and Panama hats, they lean in to listen to engines. They crouch on all fours to inspect the undersides. They assess each vehicle's authenticity, originality, and elegance in design. Steadily, they winnow down the entries. Only one car will drive up to the podium this afternoon to win Best in Show.

If past years are any indication, it's likely to be a car built before World War II. The war marked a sea change in car making, explains Dave Smith, a judge of the Prewar Sports Racing class. "After the war, we're already making production cars in America," he says. "In Europe, they're just trying to get something to eat."

The Concours is best known for its classic cars, built between the wars. Aside from the event's early years, which showcased new cars, a postwar car has only once won Best in Show. Smith has his eye on a beautiful 1937 Bugatti, an impressive car from the Keller Collection, and some fabulous Rolls-Royces—all prewar, of course.

"What are young people going to collect when they're our age?" Vivian LaVine wonders aloud. LaVine and her husband own a restoration company in Indiana; they're here with a client's gunmetal-gray 1933 Packard 1005 Twelve coupe. To her, the car embodies the best of American craftsmanship. "This is where this country started," she says, pointing to the intricate red-and-chrome hubcaps, made with an artist's technique called cloisonné. "We're losing the ability to do handmade things."

In an age of mass-production, it's hard to imagine which cars will be special enough for the Concours in 50 years. "When hundreds of thousands are built," she asks, "what makes them unique?" LaVine doesn't know what the future holds for America's classic cars, but she intends to be a steward of their legacy.

On cue, the crowds arrive by the thousands, as gilded as the cars themselves. They wear feathered hats, bow ties, turquoise jackets, and heels. They carry flutes of Champagne. The sun climbs in the sky, glinting off polished hood ornaments and sending people into the shade of cypress trees to picnic in Renoir fashion. Classical music plays over the loudspeakers. Jay Leno arrives and briefly absconds with a 1930 Böhmerland from the Eastern European Motorcycle section. The media chases behind.

By midafternoon, the emcee—the late actor Edward Herrmann—announces the best in each class. Twelve hours after he woke up, Ron Elenbaas can get his reward, driving his American Underslung to the podium to collect First in Class for the Antique division.

Only class winners are eligible to win Best in Show. The judges sequester themselves to deliberate. Anticipation builds.

The judges cast their ballots. A brass ensemble bugles a rousing tune as an offshore breeze tugs at the two American flags atop The Lodge at Pebble Beach. An envelope is produced. "And the winner is … " Herrmann reads, "the 1954 Ferrari 375 Mille Miglia Scaglietti coupe!"

Cannons blast confetti into the sky, and Jon Shirley, the former president of Microsoft, drives onto the stage with his Ferrari—a postwar winner, at last. It is painted gray, with a red interior and gill-like exhaust vents that give it the appearance of a shark.

Shirley is handed a Lalique crystal trophy, a ribbon, and a magnum bottle of Cristal. The crowd surges forward. He is describing how it drives ("It never lets you forget you're in a supercar"), when someone pokes his hand through the throng of admirers, celebrating this unusual postwar win.

"Congratulations, Jon," he says. "You broke the glass ceiling."

Shirley is all smiles. "About time, right?"

Jacob Baynham is a writer and adjunct journalism professor in Montana. He writes for Men's Journal, Outside, and Esquire.