Caroline Cassini was just 3 years old when she first attended the Concours d’Elegance at Pebble Beach, an annual assemblage of the world’s most beautiful motorcars. In the intervening years, her family has captured Pebble’s coveted Best of Show honors twice, and she is now a judge at the event.
For 21 of Ms. Cassini’s 34 years, Sandra Kasky Button has been the chairman of the famous show. “Sandra’s been an inspiration to me and a lot of women in the car world,” said Ms. Cassini, who works in collector automobile sales. “She made Pebble what it is today.”
What it is today is what many consider the world’s premier showcase for collector cars. Held each August on the 18th fairway of the Pebble Beach Golf Links near Carmel, Calif., the show highlights a full week of classic car events. These include auctions, vintage racing and a 70-mile tour by concours entrants through the area’s forests and along its famous coastline.
For Ms. Button, Pebble’s 75th anniversary show on Sunday represented the end of an era. She’s yielding her position to Vince W. Finaldi, a third-generation automotive restorer and collector who grew up in his family’s auto shops. She will stay on as the event’s brand ambassador and strategic adviser.
“There’s a lot of historical significance and emotion in passing the baton,” Ms. Button, 67, said in an interview before the event. “But I know it’s the right time. Vince is a car-crazy guy who’s at least 15 years younger than me — which are both good things. Transition, like tradition, is a necessary part of history.”
The concours began as a smallish adjunct to the popular and dangerous Pebble Beach Road Races, which ran through the area’s twisty, pine-tree-lined roads from 1950 to 1956. Phil Hill, who became America’s first Formula l world champion, is the only person ever to win both events. Today, a typical concours includes early “horseless carriage” and “brass era” models; “preservation” (unrestored) vehicles; and vintage and modern racing cars.
Because of the Big Sur fire, last Thursday’s Tour d’Elegance was rerouted and shortened to 25 miles around Pebble Beach and Monterey. One hundred and seventy-five entrants completed the route.
During her tenure, Ms. Button has overseen a substantial growth in the show’s field, from a few dozen automobiles to more than 200.
She recalled recently being motioned over at a car event by an older man using a walker. “I’ve got to tell you something,” she said he had told her. “When you were first appointed chairman, I said to my pals, ‘What does she, a woman, know about cars?’ You know what? You’ve done an awesome job.”
“Passion doesn’t really know a gender” is her response. “Yes, there are some headwinds to being the only woman in this kind of job,” she said, “but there are advantages, too. Maybe because of my gender I’m more in tune with the human element of the vehicles we show.”
Chris Bock, the show’s chief judge, singled out Ms. Button’s people skills. “At the same time,” he said, “she has an amazing eye for automotive design and historical detail. There are people who have cars in their DNA, and she is one of them.”
All told, each show receives about 2,000 applications. Though Ms. Button has the final say on special classes and featured marques, their choosing can be a yearslong collaborative process. “Someone on the selection committee will say, ‘I’ve got a dream to have these 12 cars together,’” she said. “Or a suggestion can come from outside our organization.”
Such was the case when a Texas collector, Jim Fasnacht, proposed a display of ultrarare Ruxton cars from the early 1930s. Fewer than three dozen were ever made.
“Jim was the horsepower behind that whole idea,” Ms. Button said, “up to and including transporting some people’s cars. He even hosted a dinner for all the Ruxton owners. He really brought the whole thing to life.”
A Seattle native, Ms. Button had her first driving experience at the wheel of her father’s 1965 Ford Mustang when she was 15. The first car she owned was a Datsun Fairlady sports car. “I’ve loved cars ever since,” she said.
To her, automotive beauty — the kind that merits display on Pebble’s lawn — goes beyond mere metrics. “I try to look at the whole car and what it says to me,” she said. “I wonder what the person was thinking who designed it. Either a car really sings to you or it doesn’t.”
A sampling of cars whose melodies croon sweetly: the Bugatti Type 59 (“it’s like a piece of jewelry, though I’m not certain I could get in it — I’m 6 feet tall”); a Mercedes-Benz 300 SL Roadster (“it will do everything for you on the road, and it also looks right from every angle”); a Ferrari 166 MM Barchetta (“a favorite Ferrari, very elegant and sexy”).
As the show’s overseer, Ms. Button often inherits the delicate task of soothing the psyches of car owners.
“When you put on the world’s greatest car show, you’re dealing with a lot of strong personalities,” said David Gooding, a member of Pebble’s selection committee and the president and co-founder of Gooding & Company auctioneers. “Sometimes egos get bruised.”
Ms. Cassini, now an executive at Broad Arrow Auctions, echoed that sentiment. “Pebble is widely regarded as the world’s most prestigious concours,” she said. “A win here adds both lasting reputation and financial value to a car.”
Patrick Ottis, a show judge, past class winner and widely known Ferrari restorer in Berkeley, Calif., offered this scene. “Say you have a class of vintage Ferrari racers,” he said. “Restored, the cars are worth many millions of dollars. Most of the owners are billionaires. And they aren’t used to losing.”
He added: “We’ve got 15 minutes to judge a car that cost, say, $10 million to buy and another $2 million to restore. We make a decision that it’s only going to get third place. You know how good Sandra is when you see her defuse situations like that.”
To that point, Ms. Button said: “I just try to let the wind whistle around me. To remember that I’m there for the cars. Because in the midst of all the emotion, what we do will become part of a vehicle’s legacy, and it will last much longer than us.”
Legacy is something Ms. Button does a lot of thinking about. Especially now. “We’ve got to get more young people in the cars,” she said. “It’s no fun if you don’t know how great the cars are. I love to see people bringing their kids along on rallies. They learn so much from the other collectors.”
There is welcome news on this front: “Some older-era classic cars are coming down in value,” said Ms. Button, whose husband, Martin, transports classic cars for collectors and dealers. “It’s a mixed blessing for owners, but it also opens a door, making them more affordable for new collectors.”
Another help: scholarships offered by famous Pebble forebears. The estates of both Phil Hill and Jules Heumann, Ms. Button’s early predecessor as co-chairman, support scholarships for students pursuing auto restoration degrees.
In addition, the show itself, buttressed by its $650 entry fee, has become a major supporter of area charities, recently donating as much as $4 million each year. “There was a time,” Ms. Button said, “when we weren’t even raising $75,000.”
One thing is certain. Wherever the road ahead takes her, Ms. Button won’t stop loving classic cars. Whether she’s behind the wheel of a hunky, hundred-year-old Bentley Speedster or slithering along in a slinky, ’60s E-Jag, she’ll just be steering down a new path.
