Despite his largesse, Gaines had a penny-pinching side. He would frequently stop meetings to find out who had called a particular long-distance phone number. Longtime Mad editor Nick Meglin called Gaines a "living contradiction" in 2011, saying, "He was singularly the cheapest man in the world, and the most generous." Meglin described his experience of asking Gaines for a raise of $3 a week; after rejecting the request, the publisher then treated Meglin to an expensive dinner at one of New York's best restaurants. Recalled Meglin: "The check came, and I said, 'That's the whole raise!' "And Bill said, 'I like good conversation and good food. I don't enjoy giving raises.'"