2. Joel Rosario – $1,511,016
One of only two jockeys to break the $20 million mark in 2013 purse earnings, Rosario is the defending Kentucky Derby champion jockey. He rode Orb to that milestone win and then followed up with a show at Belmont. In fact, Rosario has made a habit out of attaining horse racing success in bunches. On one day in December of 2009, the Dominican jockey recorded an incredible six victories at Hollywood Park, equaling the racetrack's record. And in 2013, Rosario managed to win two major races in just five weeks' time, crossing the finish line first in the world's-richest $10 million Dubai World Cup race (which certainly helped his earnings numbers) before going on to win the Derby. The 29-year old Rosario has earned at least $13 million in each of the last five racing seasons.