Herbert 'Herb' G. Chambers is an American businessman, the self-made billionaire Owner and President of The Herb Chambers Companies, a massive group of 60 car dealerships in the greater Boston area. Born in Dorchester, Massachusetts, in 1941, his childhood was marked by a strong work ethic: at age 13, his mother started charging him $15 per week rent, forcing him to work at a Stop & Shop supermarket.

Chambers dropped out of high school in his senior year. In 1959, he joined the United States Navy as an aviation electrician, serving four years. His post-military career began as a copy machine repairman, where he quickly recognized a structural market shift. In 1970, he founded his own copier distribution company, A-Copy America, which he sold in 1983 for a reported $80 million.

Herb Chambers started his automotive business in 1985 after purchasing an Oldsmobile-Cadillac dealership in New London, Connecticut—a decision based on his own poor buying experience at the dealership. His strategic genius was applying the aggressive sales and service model he mastered in the copier business to the high-end auto retail sector.

Under his leadership, The Herb Chambers Companies grew to 60 dealerships, representing luxury brands like Mercedes-Benz, BMW, and Porsche. He is a licensed pilot who famously commutes to his Somerville headquarters by private helicopter each Monday morning, often stopping at dealerships for meetings. His wealth is tied to the massive, long-term profitability of the high-end automotive retail and real estate sector. In December 2024, he donated $100 million to Massachusetts General Hospital for naming rights to its new oncology tower.

Herb Chambers's social impact is structural, stemming from The Herb Chambers Companies' role as a massive employer (thousands of jobs) and a dominant force in New England's auto retail market. His $100 million donation to Massachusetts General Hospital is a massive structural contribution to oncology research and patient care in the region.

His personal philanthropy supports various civic and community causes, including helping to lead the effort to bring back the Boston Police Department's mounted police unit in 2016. His career provides an inspirational narrative of a high school dropout who mastered two different industries through sheer entrepreneurial drive.

Herb Chambers maintains the professional, high-energy style of an auto retail executive. His attire is consistently formal and high-quality, favoring tailored suits. His aesthetic reflects his stability and commanding authority, often associated with his high-end exotic car collection and private helicopter commute.

Residing in Old Lyme, Connecticut, his luxury is the immense security and financial reward derived from his multi-billion dollar fortune. His life is dedicated to retail excellence, luxury brand sales, and his profound commitment to philanthropy.