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Herb Chambers is President and Owner of the Herb Chambers Companies

Wheels of Fortune, Boston Magazine

Herb Chambers conquered an industry and made himself one of the biggest players in the country. Twice. Now he’s got more money than God and everything he ever wanted. So when’s he going to start enjoying it a little?

By John Wolfson
March 2011

Herb Chambers

Herb Chambers has talked his way into two separate business empires / Photographs by Chad Griffith

AT A GATHERING OF BMW DEALERS in South Carolina, Herb Chambers found himself at the same table as a competitor he’d heard was having financial troubles. Chambers has 47 car dealerships these days. Or maybe it’s 46. It’s difficult to keep track because he’s constantly adding to his automotive empire. In all things, Chambers moves quickly when he sees what he wants. He’s been known to close a deal on a new location in half an hour, and now, sitting across the table from his weakened rival, he sensed the chance to close another.

“I was thinking, I want to buy his store,” Chambers recalls. “I knew they were struggling.” So he offered the guy a ride home to Boston on his corporate jet. “I’m thinking, If I can get him on my plane, I can talk to him. Maybe by the time we land, he might do something.”

“What time is your flight?” he asked the car dealer.

“Oh, 6 o’clock tonight.”

“We have wheels up at 1:15,” Chambers replied. “Come back with me.” The man thought about Chambers’s offer for a while. “No,” he said at last. “I don’t think I better do that.”

Win or lose, Chambers has a fondness for bold action. His collection of dealerships is now the 13th largest in the country. Or it could be 12th. (“I feel like General Custer and he’s Sitting Bull,” says his friend and competitor Jim Carney, who owns the Bernardi Auto Group. “He’s got me surrounded.”)

Specific calculations of what Herb Chambers actually owns are problematic, because, when it comes to Herb Chambers, ownership is a fluid concept. Pretty much everything in his possession will eventually be sold, and anything he wants in his possession will eventually be purchased, only to be later sold…a kind of self-perpetuating cycle of buying and selling that, when you factor in his forever-extending empire of outside business interests, makes a precise accounting of his belongings at any particular moment essentially meaningless. (“I don’t know how many companies I have,” he says. “There are probably 65 or 75 different companies — I know that we do 65 or 75 tax returns.”) However you add it up, Chambers has a lot to keep track of. He sells approximately 45,000 automobiles a year — one out of every five in eastern Massachusetts — and services another 40,000. He employs 1,900 people, has $300 million or so worth of inventory sitting on his lots on any given day, and, according to this magazine, had a personal fortune in 2006 of nearly $2 billion. But that was five years ago, and with all his buying and selling since then, who really knows how much he’s worth today?

So yes, there are a lot of important details for Herb Chambers to keep straight. And the one that’s been vexing him lately has to do with the 40,000 apples he gives away every year at his service shops. As a diabetic, he prefers to promote healthful snacking, but the gesture has created an unexpected headache. “What’s driving me crazy,” he says, his voice rising, “is I like the red apples — and at the dealership, you have to polish them — but some of them are still putting out green!” What’s this? The billionaire with 46 or 47 car dealerships is upset because his people put out the wrong color apples? Yes, and so much so that he finally called together some of his top execs to get to the bottom of the situation. “I’m going over this with people in management. So I guess we’re going to go with 80 percent red and 20 percent green. I guess some people like green.”

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