Diocles the charioteer was the most famous of his time. He won 1,462 out of 4,257 races, and was known for come from behind wins. His career lasted until he was 42 years old which was incredibly long for the sport when taking into consideration the fact that most participants were slaves and it was very dangerous. Each race stretched about 2.5 miles around the Circus Maximum in Rome. His total winnings came out to almost 36 million sesterces, which in today’s standard comes out to about 15 billion dollars. Back then that was enough to buy grain for everyone in Rome or supply the entire Roman Army for 2 months. He also most likely slept with way more women than Tiger Woods due to the lack of TMZ.