Scrooge McDuck, born out of the genius of Carl Barks in 1947, is, together with Bruce Wayne, the most famous comic book billionaire. He originally appeared as a miser anti-hero, pretty much in the same vein as his namesake, and was conceived by Barks as an antagonist for Donald Duck. Later in time, however, Scrooge McDuck, though never abandoning the original traits of wealth, frugality, thrift, and a tendency to seek even more money through treasure hunting, became a positive figure: an adventure-capitalist, who made his money by effort and overcoming difficulties of all kind. This transformation is best epitomized in the comic book series The Life and Times of Scrooge McDuck, written and illustrated by Don Rosa, and, perhaps even more so, in the TV cartoon series Duck Tales. My chapter seeks to examine different phases in the development of the character of Scrooge McDuck across the decades from the late 1940s to the early 1990s. More specifically, a selection of Barks’s and Rosa’s stories may uncover different visions of the businessman: from a cartoonish critique of the capitalist, that is, the owner of capital who pursues wealth qua wealth, to a more balanced portrait of the businessman consistent with the traditional American myth of the frontier and of enrichment through effort.