Roger Penske, founder and chairman of Penske Corporation, built one of the most influential transportation and automotive empires in the world, spanning truck leasing, logistics, dealerships, and motorsports. A racing legend turned industrial operator, Penske scaled Penske Truck Leasing and Penske Automotive Group into global leaders through disciplined execution and operational excellence. He is also an iconic force in racing as owner of Team Penske and steward of the Indianapolis Motor Speedway and IndyCar, extending his impact from business to the very infrastructure of American motorsport. Penske’s career is defined by precision, scale, and relentless performance.

Rick Hendrick, founder and chairman of Hendrick Automotive Group, built the largest privately held automotive dealership group in the United States through scale, discipline, and an intense focus on customer experience. Starting with a single dealership in North Carolina in the 1970s, Hendrick expanded into a nationwide network selling millions of vehicles annually across major brands. He is also a dominant figure in motorsports as owner of Hendrick Motorsports, one of NASCAR’s most successful teams, with multiple championships and a roster of elite drivers. Hendrick’s influence spans both retail automotive operations and the business of American racing.

Norman Braman, founder and chairman of Braman Automotive Group, built one of the largest luxury auto dealership empires in the United States by focusing on premium brands, prime real estate, and disciplined operations. Starting in the 1970s, Braman expanded aggressively in South Florida, assembling a portfolio that includes top marques such as BMW, Mercedes-Benz, Porsche, and Rolls-Royce. Beyond automotive retail, he is a prominent civic figure and philanthropist, investing heavily in healthcare, education, and urban development in Miami. Braman’s career blends entrepreneurial scale with sustained local impact.

Omar Al Futtaim, vice chairman and CEO of the Al-Futtaim Group, oversees one of the Middle East’s largest and most diversified conglomerates, with operations spanning automotive, retail, real estate, finance, and logistics. Under his leadership, the Dubai-based family empire—known for partnerships with brands such as Toyota, Lexus, IKEA, and Marks & Spencer—has expanded across the Middle East, Asia, and Africa. Al Futtaim has guided the group’s transformation through digital modernization, large-scale real estate developments, and strategic global acquisitions, solidifying its position as a cornerstone of regional commerce and one of the UAE’s most influential private enterprises.

Herb Chambers, self-made billionaire and founder of The Herb Chambers Companies, built one of the largest and most successful auto dealership groups in the United States. Starting with a single Cadillac store in 1985, he expanded into a network of more than 30 dealerships across New England, representing top luxury and premium brands such as Mercedes-Benz, Porsche, and Rolls-Royce. Known for his relentless focus on customer service and sales innovation, Chambers turned a struggling dealership into a multibillion-dollar enterprise, cementing his reputation as one of America’s top automotive entrepreneurs.