Charismatic


Looking at the payouts, he stands as the most unlikely Kentucky Derby winner of the 1990s. And that is saying something, for more than one longshot took the Run for the Roses in a decade that saw post time favorites come up short each year.

But this horse would not just be remembered for his shocking victory in North America's biggest horse race. Going from maiden claiming winner to dual classic champion to Horse of the Year, Charismatic engineered an improbable Triple Crown bid to the delight of racing fans in the spring of 1999. Though he came up short, this chestnut colt firmly stamped himself into the memories of those who watched him go for racing's most elusive prize. And by extension, the history books.

But the name of Charismatic and the Kentucky Derby were not closely linked in the early days of the young horse's career. Bred by Bob and Beverly Lewis, he visited Hollywood Park, Del Mar and Santa Anita before breaking his maiden in his sixth start, which happened to come in his return to Hollywood Park. Before then, he put up top three placings as well as off the board results.

It was not until his first foray in the maiden claiming ranks (where he raced for a $62,500 tag) in November that he picked up his diploma at The Track of the Lakes and Flowers. That was followed by two-year-old finale in the opening days of the Santa Anita winter/spring meet, where he finished third in an allowance.

Charismatic spent most of the winter and early spring at Santa Anita, but no wins came his way. The best results were a pair of second place finishes while racing at the $62,500 claiming level and later against allowance company. He also had his first stakes experience earlier in the meet, finishing off the board in the Grade II Santa Catalina. He did better in the Grade III El Camino Real Derby at Bay Meadows, taking second while narrowly missing the win, before taking fourth in the Santa Anita Derby.

Shipped out of state after that Kentucky Derby prep race, he surprised bettors with a win in the Grade II Lexington Stakes at Keeneland. That happened to be his first win in a route, as the Lexington was contested at a mile and one-sixteenth. Had he left Kentucky after that, the trip would have obviously been considered successful.

But Charismatic stuck around the Bluegrass State a little while longer.

Entered in the 125th Kentucky Derby, Charismatic did not get a lot of looks from handicappers. Despite the Lexington win and the fact he was trained by D. Wayne Lukas, who already owned several Triple Crown race wins including some Kentucky Derbies, Charismatic was sent off at over 30-1 odds. After teaming up with several jockeys by this point in his career, Charismatic found a new rider in Chris Antley, who was no stranger to Kentucky Derby triumphs.

Starting from post sixteen, Charismatic and Antley found themselves in midpack early on. But they made their move in the far turn, and Charismatic emerged in third place in the stretch before overhauling stablemate Cat Thief to close out the 1990s with the biggest win payout of any Kentucky Derby winner that decade.

Next came the Preakness Stakes, which had been won by Charismatic's sire, Summer Squall, in 1990. In an unusual occurence, Charismatic did not become the favorite at post time. In fact, he was set at odds over 8-1. But everyone who bet him that day were well rewarded for their support.

Again off the pace like two weeks earlier in Louisville, Charismatic and Antley took advantage of some decent early fractions. Making a big move in the far turn, the duo took control in early stretch as they dusted everyone to take the Preakness in front of thousands of enthusiastic fans. That left only the Belmont to sweep the Triple Crown. And twenty-one years after Affirmed became the eleventh member of that exalted club, Charismatic went to New York with a chance to expand the group to a dozen.

Unlike his last two starts, Charismatic was the top choice in the Belmont at 8-5. Emerging from post position four to the roar of a massive Belmont Park crowd, Charismatic stayed in early contention around the enormous oval. In second place much of the way, he ran into first place for a brief moment in the stretch. But his Triple Crown hopes were dashed as Lemon Drop Kid came on for the victory as Charismatic finished in third.

Immediately after the race, Antley pulled Charismatic up and held the colt's left front leg. It was discovered Charismatic sustained an injury, but he ultimately recovered from it and went on to live until the age of twenty-one before passing in 2017 at Old Friends.

Charismatic never raced again after the Belmont, but he went on to be named the Champion Three-Year-Old colt and Horse of the Year for 1999. He also entered stud, becoming a stallion stateside as well as in Japan before returning to North America. Among his most notable progeny was Sun King, a graded stakes winner who counted the Grade III Tampa Bay Derby and Grade II Pennsylvania Derby among his triumphs.

He became the most popular horse in the sport in the spring of 1999. And that run at the tail end of the twentieth century gave him staying power, for Charismatic has been remembered fondly since his racing days all those years ago.

Was he a winner? Absolutely.

Was he a champion? Certainly.

Was he charismatic? Definitely.


Entry added November 3, 2021 by AF.