Herb Chambers

Herb Chambers made his fortune as a major New England auto retailer, with 60 dealerships at the company's peak. He sold all but one of his stores to Asbury Automotive in July 2025.

Chambers grew up in Boston's working-class Dorchester neighborhood, where he got his first job as a cart collector at the local supermarket.

He dropped out of high school during his senior year and joined the U.S. Navy.

After returning, he borrowed $500 from his mother to start his first company, a copy distributor, which he sold for $80 million in 1983.

Chambers then stumbled into the car sales business, purchasing a Cadillac dealership that had given him poor service.