Charismatic (カリズマティック karizumatikku; born 1996) 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 Secretariat via Weekend Surprise, and his broodmare was Bali Babe. His succession from Weekend Surprise gives him blood relation to A.P. Indy.
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 1 1/4 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. 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.
Charismatic also won the 124th Preakness Stakes on May 15 with a time of 1:55.20 around the 1 3/16 mile track. He was 1 1/2 lengths ahead of Menifee, again second, with Badge finishing third. Despite the Kentucky Derby win, Charismatic was still not the favorite to win, posting 8-1 odds. Menifee was actually the favorite at 5-2.
At the 131st Belmont Stakes on June 5, however, Charismatic was a 2-1 favorite, with Menifee second in odds at 7-2. The rivalry between Charismatic and Menifee was compared to Affirmed and Alydar in 1978. Charismatic looked like he would become the first horse in 21 years to win the Triple Crown, taking the lead in the final furlong. However, the horse faded, and lost the lead to eventual winner Lemon Drop Kid with 1/8 mile to go, ultimately finishing third behind second-place Vision and Verse. Sensing something wrong, Chris Antley dramatically jumped off Charismatic and held up the colt's left front leg. Indeed it was broken in two places. Many say Antley's actions saved Charismatic's life, and the horse underwent career-ending surgery the following morning. The moment was selected by racing fans as the 1999 National Thoroughbred Racing Association Moment of the Year.
Charismatic finished his career with 5 wins, 2 places and 4 shows in 17 career starts, for total earnings of $2,038,064. He won the Eclipse Awards for 3-year-old Colt of the Year and Overall Horse of the Year for 1999.