In the boom years of the 1920's, Americans bought automobiles in record numbers and Charles Jennings was one of the dealers who benefited. He opened his New York Dodge dealership in 1924 and by 1927, he was selling $10 million worth of cars a year. Jennings, a Norwich, Connecticut native, graduated Phi Beta Kappa from West Point in 1902 before earning his mechanical engineering degree from Lehigh. He also was a member of Tau Beta Pi honorary engineering fraternity. "The combination of education and experience explains in a measure the forward march of his business," wrote the Journal of Commerce.
Before joining the Dodge Motor Company in Detroit in 1920 as director of sales, Jennings worked for several companies, including the Otis Elevator Company, Matheson Motor Car Company, and Alco Motors. As a hobby, he took up golf and developed into an excellent player, winning the Senior U.S. Golf Championship at Rye, New York, in 1934. In 1940, he won the Metropolitan Senior Championship at Garden City, New York, and twice he won the Winter Golf League of Advertising Interests at Palm Beach, Florida. Jennings remembered Lehigh, his second alma mater, through a bequest for scholarships.