Winston R. Pittman, Sr. is the president and CEO of Pittman Enterprise, one of the largest African-American auto dealers in the nation. He owns seven dealerships that span four states and encompass nine brands, including Toyota, Lexus, Subaru, and Chevrolet stores in Georgia; Ford and Nissan in Ohio; Buick/GMC/Cadillac in Kentucky; and Lexus in South Carolina.

Winston was born in Grenada, Mississippi, to Mary Lee Purnell Pittman and W.C. Pittman. He studied accounting at Jackson State University before beginning his career at United Parcel Service as an unloader. Within three years, he had worked his way up to hub manager. He transitioned to the automobile industry in 1975 and advanced his way through the ranks, working as a car salesman, used car manager, new car manager, and finance and insurance manager until he was promoted to general manager in 1983.

Winston entered the Chrysler Dealer Development Program in 1986, graduating in 1987. He purchased his first store—Cardinal Dodge in Louisville, Kentucky—in 1988. Since then, he has owned Dodge, Chrysler, Jeep, Pontiac, GMC, Dollar Rent-a-Car, Mercedes, BMW, Lincoln, Mercury, Subaru, Chevrolet, Ford, Nissan, Buick, GMC, Toyota, and Lexus franchises.

A firm believer that no one achieves success on their own, Winston prioritizes giving back to the community, the automotive industry, and minority programs. He is a former president and board member of both the DaimlerChrysler Minority Dealer Association and the Toyota Lexus Minority Dealer Owners Association and has served on the National Dodge Dealer Council, the National Association of Minority Automobile Dealers, the Toyota National Dealer Council, and the Lexus National Dealer Council.

Winston has been recognized with numerous awards for his success and contribution to the automotive industry. He was named Black Enterprise’s Dealer of the Year in 2002 and was honored with the Lifetime Achievement Award from the National Association of Minority Automobile Dealers in 2006, among other accolades. He has also been profiled in several national and local publications including Ebony Magazine, Black Enterprise, Courier Journal, Forbes, Dollars and Cents, and National Dealers Publication, and has been inducted into the HistoryMakers in the BusinessMakers category, with his oral history archived in the Library of Congress.

Winston is a proud and active member of Quinn Chapel African Methodist Episcopal church in Louisville, Kentucky, serving as steward pro tem and church treasurer. He teaches the Boyz to Men class, and was recognized for his exemplary leadership and service to the church and community in 2010.

Mr. Pittman resides in Louisville, Kentucky with his wife, Alma, whom he has shared a loving marital union with since 1971. They are proud parents of three children: Winston R. Pittman Jr., Misty Withers, and Jabari D. Pittman; son-in-law, Marcus D. Withers; daughter-in-law Sarita K. Pittman; and their beautiful grandchildren, Kennedy Skye Withers and Marcus Withers II.