Michael Moore accumulated a $50 million fortune by making documentaries bashing capitalism. Moore – who wears a trademark baseball cap to communicate that he’s a regular, working-class guy – nevertheless got “outed” in his divorce in which it came to public light that he and his wife owned nine properties in Michigan and New York, including a 10,000-square-foot lakefront home in Traverse City and a Manhattan condo so large that it was once three separate apartments.48.