Oliver Lewis was champion jockey of the Kentucky Derby in 1875 with a winning race time of two minutes and 37 seconds. Jockey Willie Simms won in 1896, bringing his horse in at two minutes and seven seconds. James Winkfield was the winning jockey in both 1901 and 1902 with winning race times of two minutes and seven seconds and two minutes and eight seconds, respectively. Each of these men possessed the skill and power necessary to spur a horse to glorious victory. All are members of the small, select group of Derby-winning jockeys who were African Americans. The stakes were high: Black jockeys who won a race in the late 1700s and 1800s sometimes won freedom from slavery as well. This work examines the presence of black jockeys in the Kentucky Derby, from the first instance of slaves working as stable hands and tending their masters' horses to the first black jockey to win the prestigious Kentucky Derby in 1875 and the continued participation of black jockeys in the Kentucky Derby. Black owners and trainers in the Kentucky Derby are also discussed. Three appendices list black winning jockeys, black trainers and black owners of Kentucky Derby horses.