66. Carmen Policy
Location: Restaurant in St. Louis
Initial cost: Unknown
Amount added: $100*
Carmen Policy is a well-known figure among both legal professionals and football enthusiasts. As an accomplished attorney and executive, he notably contributed to the success of the San Francisco 49ers in the 1980s and 1990s. He also invested in the Cleveland Browns, eventually selling his share in the early 2000s.
Despite amassing a significant wealth, Carmen Policy, hailing from Youngstown, Ohio, showcases his humility in gestures like leaving a $100 tip on a modest dinner bill at a St. Louis restaurant, demonstrating a generosity not always mirrored by his executive peers.