James Caldwell was born on a small tobacco farm in Enfield, Connecticut. He paid his way through Georgetown University by tutoring. After serving in the U.S. Navy during World War I, he resumed his studies at Trinity College.
At age 27, with a background in rubber chemistry, Caldwell became a vice president of Seamless Rubber Company. His knowledge of rubber's ability to wear well, hold color, and be molded led him to the idea for a line of molded rubber products for use in the kitchen. Although the Great Depression had hit, Caldwell resigned his vice presidency and moved his family to Norton, Massachusetts, where he contracted to have the first of his rubber products molded.
Caldwell sold his items door to door and then moved to Akron, Ohio, the center of the U.S. rubber industry. He took over a plant that was making balloons and began mass-producing his products. After becoming president of the Wooster Rubber Company in 1934, he saw the company evolve into Rubbermaid, Inc. in 1957.