Won the 1900 Sir Thomas Lipton Cup yacht race. In 1904, he set a new land speed record of 92.30 mph at the Daytona Beach Road Course (Ormond Beach, FL). That same year, he launched the Vanderbilt Cup, the first major trophy in American auto racing.
His first wife was the daughter of U.S. Senator James Graham Fair, credited with discovering the Big Bonanza, one of the richest pockets of gold and silver of the Comstock Lode.