Consuelo Vanderbilt was one of the most famous heiresses in U.S. history. She was astonishingly beautiful, one of the wealthiest young women in the United States. By the time she she'd made her debut in 1895, the entire country knew she possessed $20 million — a sum equal to almost $4 billion today. She is pictured here with a young Winston Churchill in 1904. He was one of her favorite cousins from her first marriage to Charles Spencer-Churchill, 9th Duke of Marlborough.