Charismatic: A Real-Life Story of Elation and Heartbreak

Charismatic and jockey Chris Antley after winning the 1999 Kentucky Derby.
Charismatic and jockey Chris Antley after winning the 1999 Kentucky Derby. (Jeff Burkhart/BloodHorse photo)

The sports world is filled with events that are regarded as storybook tales. They are the times when heartwarming stories unfold as if they are scripted and not chapters of everyday life where skill, talent, and luck determine the outcome.

The reality, of course, is that storybook finishes are simply for storybooks. As much it would be so fitting or grand for something to happen, that alone is not enough reason to alter fate.

That lesson was painfully taught in 1999 when a 3-year-old colt named Charismatic chased a Triple Crown sweep.

Charismatic embodied everything tied into his name.

If he had anything at all, Charismatic had charisma. He ran for a claiming tag a couple of times and then won the Kentucky Derby and Preakness. His owners, Bob and Beverly Lewis, were beloved figures in the sport who won two legs of the Triple Crown in 1997 with Silver Charm. His trainer, D. Wayne Lukas, was the sport’s living legend. His jockey, Chris Antley, was trying to revitalize a career sidetracked by substance abuse.

Charismatic and D. Wayne Lukas
Charismatic and D. Wayne Lukas (Skip Dickstein/BloodHorse photo)

At the quarter pole of the Belmont Stakes, Charismatic led by a head and, yes, a storybook finish was in the offing. But in that final quarter-mile, reality set in. Not only did Charismatic tire and finish third but shortly after he crossed the finish line, the reason for his fatigue became tragically evident. Charismatic suffered a career-ending fractured leg in the Belmont and the injury might have been fatal if Antley had not hopped off and cradled the horse’s injured leg until medical help arrived.

It was a storybook tale that ended with a nightmare.

It was real life.

“They were great memories. Charismatic was a very special horse owned by very special people,” Lukas said last week. “I would have liked to see it go all the way to the end, but it wasn’t in the cards.”

When Charismatic debuted for Lukas and the Lewises on June 20, 1998 and gave off little indication of the glory awaiting him a year later. Purchased for $200,000, he finished last in a field of six as the 12-1 longest shot on the board.

Through five career starts, Charismatic was still a maiden. Frustrated by the talent he saw in the colt and the lack of results, Lukas finally decided to drop Charismatic into a Nov. 28 maiden race with a $62,500 claiming tag to wake up the 2-year-old. The son of Summer Squall responded with an easy five-length score under Hall of Famer Laffit Pincay Jr.

Yet the victory did little to change Charismatic. He finished no better than third in his next three races and was a well-beaten fifth in the Grade 2 Santa Catalina Stakes, though Lukas maintained his belief that beneath the surface there was enough talent to run in the Kentucky Derby.

Again, Lukas entered Charismatic in a $62,500 claimer. The date was Feb. 11 and the Kentucky Derby was less than three months away. Charismatic crossed the finish line second by a neck but received credit for the victory through a disqualification.

Charismatic was second in an allowance race after that and then second by a head in the G3 El Camino Real Derby. Lukas then ran him in the Grade 1 Santa Anita Derby and Charismatic checked in fourth, 8 ¼ lengths behind the victorious General Challenge.

Undaunted, Lukas gave Charismatic one last chance to prove he was worthy of being on the Triple Crown trail. He shipped Charismatic to Kentucky for the Grade 2 Lexington Stakes at Keeneland on April 18 and perhaps there was something magical in the spring air in the Bluegrass.

Charismatic registered a 2 ½-length victory in the Lexington, punching his ticket to the run for the roses at Churchill Downs.

With just two wins in claimers and the Lexington to his credit, Charismatic was overlooked despite his connections. He was sent off at 31-1 odds in the 1999 Kentucky Derby, a race in which the Bob Baffert-trained entry of General Challenge and Excellent Meeting were favored. Baffert was seeking a third straight win in the run for the roses.

Jerry Bailey, who rode Charismatic in the Lexington, opted to ride Worldly Manner (seventh) in the Derby, so Antley was brought in for the opening leg of the Triple Crown.

Whatever happened in the Lexington carried over to the Derby as Charismatic rallied from seventh to move into second at the eighth pole, a half-length behind Cat Thief, another Lukas runner.

Charismatic forged to the front at the sixteenth pole and then held off a late bid by Menifee to give Bob and Beverly Lewis their second Derby win in three years and Lukas his fourth overall.

Two weeks later in the Preakness, Charismatic was viewed as a one-hit wonder. Despite winning the Derby, he was sent off at 8-1 odds while Menifee was the 2-1 favorite.

The Preakness was similar to the Derby, except that Charismatic posted a more decisive victory. Tenth early on, Charismatic surged to a three-length lead at the eighth pole, and had a big enough margin to hold the late-charging Menifee safe by 1 ½ lengths and arrive on the doorstep of becoming the first Triple Crown winner in 21 years.

“I took some chances running him in a claimer,” Lukas said. “I tried everything I knew as a horseman to turn him around and then to see it all come together in the Derby and Preakness was pretty gratifying.”

After the Derby and Preakness, the Charismatic bandwagon became standing room only territory. The combination of a former claimer, owned by Bob and Beverly Lewis and trained by Wayne Lukas with jockey trying to rebuild his career made the colt a national hero heading into the Belmont Stakes, where Charismatic faced a mile-and-a-half test that could put him the same company as Secretariat, Settle Slew, and Affirmed.

This time, the fans made Charismatic an 8-5 favorite over 11 foes with his archrival Menifee the 5-2 second choice.

On this occasion, Menifee did not fire and finished eighth.

Meanwhile, Antley and Charismatic uncharacteristically pressed the pace of the filly Silverbulletday from second and when she tired approaching the quarter pole, Lukas’ colt grabbed the lead and launched his bid for racing’s greatest measure of glory.

Yet this time, Charismatic could not pull away. He lacked the stretch kick that propelled him to victory at Churchill Downs and Pimlico. Lemon Drop Kid, a 29-1 shot, caught him and edged way to a half-length lead over the Derby-Preakness winner at the eighth pole.

In that final furlong, 54-1 shot Vision and Verse also passed Charismatic and battled with Lemon Drop Kid to the wire in a duel that went to Lemon Drop Kid by a head.

A length and a half behind them, Charismatic followed in third, another Triple Crown bid foiled.

The sense of disappointment at Belmont changed to shock in the next moment when Antley suddenly jumped off Charismatic shortly after he passed the finish line.

As gasps filled the grandstand and all heads turned to see what happened, Antley held Charismatic’s left leg, not allowing the powerful colt to put weight on the injured leg and do more damage to it.

As Daily Racing Form columnist Jay Hovdey so simply yet eloquently wrote at the time, “The Triple Crown was lost, but Charismatic was saved.”

Charismatic fractured the cannon and sesamoid bones of his left front leg, injuries severe enough to end his racing career with a record of 17 starts, five wins and earnings of $2,038,064, yet he healed well enough to enter stud at Lane’s End Farm in Kentucky.

“It was a shame what happened in the Belmont,” Lukas said. “He should have won the Belmont. He was the best horse.”

At the end of the year, Charismatic was rewarded with the Eclipse Award as the champion 3-year-old male of 1999.

In a powerful sign of the emotions stirred by the poignant and yet heartbreaking scene of Antley protecting Charismatic’s shattered leg, the image was voted by fans as the National Thoroughbred Racing Association’s Moment of the Year.

Nearly 20 years later, that scene with Antley and Charismatic is probably what is remembered most about the champion colt.

Yet in a storybook or Hollywood script that never would have happened. Instead, Charismatic would have taken the lead at the top of the stretch and dashed off to a spot in the Hall of Fame. But what happened on June 5, 1999 in the Belmont Stakes was a real-life, flesh-and-blood story that flies in the face of sentiment and reminds us that nothing should be taken for granted – even if it is the perfect storybook ending.

Fun Facts About Charismatic

  • He was bred in Kentucky by Parrish Hill Farm and W.S. Farish.
  • Charismatic had seven different riders in his 17 starts.
  • The Belmont Stakes marked only the fourth time Charismatic was favored in a race.
  • Charismatic was the subject of a 30 for 30 episode on ESPN.
  • After a career at stud in the United States and Japan, Charismatic was returned to his home state of Kentucky in 2016 through funding by the Robert and Beverly Lewis Family Foundation, Tito’s Handmade Vodka, and Charismatic’s Inner Circle. He lived out the remainder of his life at the Old Friends Thoroughbred retirement farm before passing away on Feb. 19, 2017.

newsletter sign-up

Stay up-to-date with the best from America's Best Racing!