SUGAR RAY ROBINSON — CADILLAC 1950, EST. $5,000
Intelligent, charismatic, stylish, and dangerous inside the ring, Sugar Ray Robinson is one of the very few all-time greats of boxing. The Georgia native started earning money at a young age by tap dancing, but soon he realized that boxing is more of his speed. He entered pro boxing in 1940 and soon emerged as the people’s champion, someone whom you can risk your earnings.
The lovable rogue and natural showman never had to look back and had sufficient money to get his hands on luxury cars and houses. He bought a Cadillac 1950 for $5,000 and painted it fuchsia. $5000 might not be a staggeringly high amount today, but it was an outrageous amount back in the 1950s.