Charismatic, who took fans on an unforgettable ride through the 1999 Triple Crown trail, has passed away at Old Friends , the Thoroughbred Retirement Center near Georgetown, Kentucky. The 21-year-old pensioner had been repatriated from his longtime stud home in Japan fewer than three months ago.

The most recent of four Kentucky Derby (G1) winners trained by Hall of Famer D. Wayne Lukas, Charismatic emerged as an unlikely hero, but his unexpected rise made him all the more lovable.

The flashy chestnut needed six starts to break his maiden as a juvenile, and only accomplished it when dropping in class to a $62,500 maiden claimer (meaning that other connections could step in and purchase him – “claim” him – for that price). No one took him.

Charismatic again found it too tough when stepping back up in class for a pair of allowance races at Santa Anita, and he trailed home last of five when attempting graded stakes rivals in the Santa Catalina (G2). Ironically, the Santa Catalina has since been renamed in honor of the late Robert B. Lewis (G3), who campaigned Charismatic with his wife, Beverly.   

Lukas put Charismatic in another $62,500 claiming race. Although narrowly beaten, Charismatic was hampered by a rival, and he was awarded the win via disqualification. No one took him.  

Still trying to get Charismatic to put it all together, Lukas continued to give him class tests. He began to respond with a fast-finishing near-miss in the 1999 El Camino Real Derby (G3), only to go backward next time when a distant fourth in the Santa Anita Derby (G1).

Why wasn’t Charismatic living up to his glimmers of talent? What piece of the puzzle was missing?

Lukas discerned it: Charismatic was the type of horse who thrived on a demanding regimen, indeed required intense training and a busy race schedule to get and stay fit. The ordinary work patterns just weren’t enough for him. The Hall of Famer made the right adjustments, and the rest was history.

Wheeling back from his Santa Anita Derby flop, Charismatic looked like a different animal with a resounding victory in Keeneland’s Lexington (G2) in a fast time. In fact, he still owns the stakes-record time of 1:41 for the 1 1/16-mile event.

Charismatic was clearly on the upswing entering the 1999 Kentucky Derby. But his overall resume wasn’t as appealing as the top contenders, including his own stablemate Cat Thief, widely regarded as Lukas’ better chance.

Overlooked at odds of 31-1, Charismatic completed his transformation from claimer to Derby winner. He surged past Cat Thief in the stretch and did enough to hold off the late charge of Menifee by a neck.

 Adding to the inspirational tale was Charismatic’s jockey, Chris Antley, who was in the midst of a comeback after battling drug and weight problems. The colt who turned his career around, and the former top rider who was turning his life around, had only just teamed up for the first time in the Derby. They hit it off as though they belonged together.

Two weeks later in the Preakness (G1), Charismatic still had some doubters and went off at 8-1. He silenced them by going out and defeating Menifee handily by 1 1/2 lengths. Charismatic thus completed a father-son Preakness double with his sire Summer Squall, the 1990 Preakness winner who had previously been runner-up to Unbridled in the Kentucky Derby.

Could Charismatic be the one to end the Triple Crown drought? Unfortunately, the dream came to an end in the Belmont S. (G1), where Charismatic uncharacteristically argued the pace instead of employing his trademark late swoop.

As Lemon Drop Kid went on to victory, and Charismatic tired to third, his loss suddenly turned tragic. Charismatic broke down after the wire.

In the heartbreaking moment, Antley’s spontaneous reaction is often credited with saving Charismatic’s life. Antley jumped out of the saddle and took hold of Charismatic’s injured left front leg, preventing him from suffering further, and possibly catastrophic, harm.

Charismatic underwent successful surgery and embarked upon a new life at stud, eventually moving to Japan in 2003. His top performers were Sun King (in the U.S.) and Wonder Acute (in Japan). Charismatic also factors as the maternal grandsire (broodmare sire) of Wicked Strong, who was fourth to California Chrome in the 2014 Kentucky Derby.

Retired from stallion duty, Charismatic was brought home to Kentucky on December 3, and had been enjoying life at Old Friends .

Antley didn’t have a happy ending, dying the year after Charismatic’s amazing run that saw him crowned champion three-year-old colt and Horse of the Year. But the gifted rider was posthumously enshrined in the Hall of Fame in 2015.

Now Antley and Charismatic are together again.

Photo of Charismatic at Old Friends copyright/courtesy of Jennifer Caldwell