Defending Rolex champion David O’Connor will be looking to make it two in a row, an attainable feat for the reigning Olympic champion who last year won the Rolex Kentucky Three-Day Event in dramatic fashion on Giltedge, owned by Jacqueline Mars. His wife and 1999 victor, Karen O’Connor, may pose the biggest threat, as she has received special permission to start four horses in the competition that usually limits riders to three horses each.

Another family connection to watch is the father and son team of Bruce and Buck Davidson, who will each be riding three horses. Two-time World Champion and five-time Olympian Bruce Davidson will be looking for his first win in the four-star division at Rolex Kentucky while his son, Buck Davidson, 26, will be hoping to improve on his sixth place finish of 1998.