In the 1970s, horse racing had three Triple Crown winners in six years – something that had not been accomplished since the 1940s. But in that decade, we came close to seeing three Triple Crown winners in four years, if it weren’t for an ill-fated move by a Hall of Fame jockey to the front of the field in the middle of the longest race of the three.
Pensive was not a highly regarded colt heading into the 1944 Kentucky Derby, having won just one stakes race and suffering from tender hooves for most of his career. All eyes were on Stir Up, a gelding who had won the Flamingo Stakes and a division of the Wood Memorial.
Stir Up seemed in good position, stalking the leader, Diavolaw from third place. Pensive was in 13th place in the 16-horse field but trapped along the outside, so jockey Conn McCreary sent the Calumet Farm horse along the rail around the turn. He was 12 lengths behind at one point, but sped past the front-runners in the homestretch en route to a 4 1/2-length win.
Bettors made Pensive the 8-5 favorite one week later in the Preakness Stakes, and he didn’t let his fans down. He was in third place after a mile, 4 1/2 lengths behind Stir Up, who went to the lead early. Pensive slowly made up ground, but with less than a furlong to go, he put on the same burst of speed he used in the Derby, flying past Stir Up and Platter to win by 3/4 of a length.
He was set to become the seventh horse to win the Triple Crown as the 1-2 favorite in the Belmont Stakes, but inexplicably – as jockey Ron Franklin would do 45 years later – McCreary sent Pensive to the front chasing a speedy pacesetter, Who Goes There. He was within a length of the lead with a mile to go. Who Goes There tired, and Pensive seemed destined to finish as the Triple Crown winner.
But Pensive tired in the long Belmont homestretch, his final kick left behind on the backstretch, leaving Bounding Home to win by only 1/2 length. It was the first time a horse that had won the Kentucky Derby and Preakness Stakes lost the Belmont – a feat to be replicated a frustrating number of times in the future.
The Belmont was the beginning of nine consecutive losses for Pensive, who never found his Triple Crown success again and was retired . He died in 1949 of a twisted intestine.
Pensive was the first of three generations of Derby winners, a feat accomplished only twice in Derby history. He was the sire of the 1949 Derby winner Ponder, who in turn sired Needles, the winner in 1956.