Malcolm Forbes
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Millionaire Malcolm Forbes didn't start riding until late in life, but made up for it with a Harley stationed at each of his houses, not to mention one on his private plane and another two on his yacht. He founded a club, the Capitalist Tools MC (which survives him) and had a hot-air balloon made in the shape of a Softail.
He once commissioned Craig Vetter to make a custom Vetter Fairing for him which Craig flew to New York to deliver.