It was late in the afternoon on Feb. 20, 2010, when the last golden rays of sunlight shone brightly on the main track at Gulfstream Park, casting long shadows as 10 talented Thoroughbreds galloped in a pack down the backstretch during the historic Fountain of Youth Stakes.
Poised in second place, carrying the blue and yellow silks of Zayat Stables, was a striking chestnut colt named Eskendereya. On the eve of his actual third birthday, the son of Giant’s Causeway was positioned to vie for victory in what was then a 1 1/8-mile race, tracking a longshot pacesetter through modest early fractions.
As a juvenile, Eskendereya had raced exclusively on turf and synthetic tracks, winning the Pilgrim Stakes before finishing ninth in the Breeders’ Cup Juvenile. In his dirt debut at Gulfstream, Eskendereya had forged to a hard-fought victory in a 1-mile allowance race — a solid effort, but hardly indicative of future stardom.
But as Eskendereya thundered around the far turn at Gulfstream Park, heading toward the homestretch where Derby contenders are separated from Derby pretenders, something amazing happened.
Eskendereya began to widen at will.
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The Todd Pletcher-trained colt had taken the lead under his own power heading into the far turn, and approaching the top of the stretch — when jockey John Velazquez asked Eskendereya for his best effort — the copper competitor lengthened his stride and powered clear of the pack. His pursuers, under hard urging to keep up, fell back in vain as Eskendereya put the pedal to the medal, his legs pumping like pistons as he sprinted the final three-eighths of a mile in a blazing :36.46.
Three lengths. Four lengths. Five lengths. Seven lengths. Like a rhythmic machine Eskendereya ran straight and true down the stretch, widening his lead with every stride as Velazquez urged him on. At the finish line, which he reached in 1:48.87, Eskendereya was 8 1/2 lengths in front, alone in the shadow of the grandstand as racing fans applauded his perfomance.
It was a tour-de-force effort, by every metric one of the finest of the decade in a Kentucky Derby prep race. From start to finish Eskendereya was in control, running for the sheer joy of running, dominating his rivals simply because he could.
And his rivals, overmatched as they were, were hardly slouches. Quite to the contrary, Eskendereya defeated an exceptional field in the Fountain of Youth, making his decisive triumph all the more extraordinary.
In order of how they finished, Eskendereya’s beaten foes included…
…Jackson Bend, who went on to finish third in the Preakness Stakes before winning the Forego (G1) and Carter Handicap (G1) as an older horse.
…Aikenite, a multiple Grade 1-placed juvenile who would go on to win the Commonwealth Stakes (G2) and Churchill Downs Stakes (G2) as a 4-year-old.
…Pleasant Prince, who subsequently finished second by a nose in the Florida Derby (G1) before winning the Ohio Derby (G3) and Oklahoma Derby later in the season.
…Ice Box, future winner of the Florida Derby (G1) and runner-up in the Kentucky Derby.
…Pulsion, runner-up in the Norfolk Stakes (G1).
…Positive Split, a maiden winner at Keeneland.
…Prince Will I Am, who would go on to win the Jamaica Handicap (G1), W. L. McKnight Handicap (G2) and Mac Diarmida Stakes (G2).
…Buddy’s Saint, winner of the Nashua Stakes (G2) and Remsen Stakes (G2) as a juvenile.
…Lost Aptitude, runner-up by a head in the Tropical Park Derby (G3).
For Eskendereya to obliterate such a quality field was astonishing and the mark of a truly special horse. He later proved his performance was no fluke by scoring a 9 3/4-length victory in the Wood Memorial (G1), emerging as a heavy favorite to win the Kentucky Derby.
Unfortunately, an injury shortly before the Run for the Roses prompted Eskendereya’s retirement to stud. While he was unable to showcase his talent in the classics, his name lives as the sire of Mitole, the popular champion male sprinter of 2019.
Ten years have passed since Eskendereya caused jaws to drop with his demolition of the Fountain of Youth. To this day, we still wonder what might have been if only Eskendereya had stayed sound.
J. Keeler Johnson is a writer, videographer, handicapper, and all-around horse racing enthusiast. A great fan of racing history, he considers Dr. Fager to be the greatest racehorse ever produced in America, but counts Zenyatta as his all-time favorite. You can follow him on Twitter at @J_Keelerman.