Herb Chambers lives and drives cars. In Boston, where one out of every three luxury-car owners owns a Herb Chambers–sold vehicle, it’s become something of a parlor game counting Herb Chambers dealerships and the cars in his personal collection. Let’s see, there’s the Maybach dealership in nearby Somerville, the Rolls Royce and Bentley dealership in Wayland and the four Mercedes dealerships. There’s the 1995 Mercedes Gullwing that raced in Cannonball Run, the lipstick-red 10-cylinder 2006 Porsche GT, the 552-hp Bentley GT, oh and the 645-hp Mclaren F1 that made Jay Leno so jealous he had to go out and buy his own. Sometimes it seems as though it’s Herb Chambers’s world and the rest of us just ride in it. His company, the third largest dealership in the country, whose ranks are filled with loyal staffers who’ve been with him for years, even has its own ring, just like the Super Bowl: the Herb Chambers Ring, a lug-nut-sized diamond-encrusted sparkler inscribed with the letters HC, awarded to the top Herb Chambers salesperson of the year. “That’s what people want, even more than the money,” says Lawrence Skinner, GM of Chambers Cadillac.
The thing is, as much as Herb Chamber loves cars, he doesn’t much like schmoozing, drinking and hanging out with other car people, unless they work for him. Which brings us to his second most burning passion: his Gulfstream 450 and TK-passenger Bell 407 helicopter.
“In this business you need to be everywhere at once,” he says. “I have to check in at my dealerships — and we’re up to 38 at this point — and I have to regularly meet with each one my manufacturers, and we’re carrying 28 different brands now. I don’t mind doing it, but I hate the drinking and going out at night afterward. With the G4 and the Bell, I can fly from Boston to Detroit Dusseldorf for a meeting, and fly right back home, or fly around and hit 12 of my dealerships in an afternoon.”
As he speaks, he’s standing at his latest dealership, a 50,000-square-foot Lexus Xanadu in Sharon, Massachusetts. With its 50-foot windows, soaring white walls, polished granite floors, plasma-screen lounge and complete complimentary food and beverage service, it looks like nothing so much as a cross between a car dealership and first-class airport terminal. Chambers has just a few minutes to look things over and try out the coffee. The Bentley sits flexing on its haunches outside, the Bell waiting at the helipad to take him out to the G4. Before can go, though, he notices that on the counter of the barista bar someone has put out a tip jar. This is bad. In Herb Chambers World you don’t ask people to pay $100,000 for a car and then ask them for a tip.
“Excuse me for a second . . . what’s this?” he turns to the young woman behind the counter, who suddenly turns as red as Chambers’s 10-cylinder Porsche. “Get it out of here. Now, where was I?”
