Charismatic is a stallion Thoroughbred horse, and is known as one of the closest challengers to the Triple Crown of Thoroughbred Racing since the last winner, Affirmed, accomplished the feat in 1978. He was trained by D. Wayne Lukas, and famously ridden in the Triple Crown races by Chris Antley. Today, he stands at stud at Iburi Stallion Station in Japan, operated by the Japan Bloodhorse Breeders Association.
His sire was Summer Squall, making him a third-generation descendant of both Secretariat and Northern Dancer, and his broodmare was Bali Babe. His succession from Weekend Surprise gives him blood relation to A.P. Indy, while his grandsire, Storm Bird, gives him blood relation to Storm Cat and Birdstone. He was bred under a foal-sharing arrangement between William S. Farish and the Parrish Hill Farm of Dr. Ben and Tom Roach.
Charismatic did well as a two-year-old, but was put on claiming races by his owner, Bob Lewis, twice, as recently as February 11, 1999, only three months prior to the Kentucky Derby.
He was a 31-1 longshot in the 125th Kentucky Derby on May 1, 1999, but won the race with a time of 2:03.20 around the 1Â¼ mile track. Charismatic finished by a head in front of Menifee, giving Menifee's trainer Elliott Walden his second Kentucky Derby place showing in only his second entry. Cat Thief, also trained by Lukas, was third, and had led most of the race. The win denied Lukas' rival trainer Bob Baffert of his third straight Derby victory. His three entered horses, two of which were co-favorites at 9-2 odds, failed to make the top three.