In the recent Horse of the Year debate involving Justify and Accelerate, a segment of racing fans and media punditry found it difficult to fathom how a Triple Crown winner should not also earn the season’s top honor. In a slightly different vein, it might also be difficult to imagine how a horse that nearly won the Triple Crown could walk away empty-handed at season’s end with no divisional honors whatsoever.
Four horses have won both the Kentucky Derby (G1) and Preakness (G1) but lost the Belmont Stakes (G1) by one length or less. Three of these — Silver Charm (1997), Real Quiet (1998), and Smarty Jones (2004) — accomplished the feat rather recently, and all three eventually earned three-year-old champion colt honors.
The first such occurrence was 75 years ago in 1944. Calumet Farm‘s Pensive became the sport’s first near-miss in the Triple Crown series when he lost the Belmont by a mere half-length, the closest margin of defeat in that race by a Triple Crown candidate until Real Quiet missed by a nose 54 years later. In what can only be attributed to a subsequent meltdown in form, not only was Pensive not named champion three-year-old colt at season’s end, but he could not even claim to be the best of his age in his own barn.
After several appearances in overnight company to start the year, Pensive crammed in all of his pre-Kentucky Derby stakes attempts into an 18-day window during the month of April. All were held at Pimlico, where racing in Maryland had been consolidated that spring due to World War II-related travel restrictions.
After defeating the accomplished older horses Porter’s Cap and Sun Again in the six-furlong Rowe Memorial Handicap on April 12, Pensive settled for second in the Bowie Handicap three days later going one mile and 70 yards. That, too, was against older horses, but he returned to his own division on April 29 when he finished second in the 1 1/16-mile Chesapeake Stakes.
Judged by trainer Ben Jones as the stable’s best classic prospect, Pensive was Calumet’s lone representative in the May 6 Kentucky Derby, though he nearly missed the race after reportedly picking up a nail in his final work. Sent away as the 7-1 second choice, he rallied from far back to win comfortably by 4 1/2 lengths under Conn McCreary.
The winning margin was narrower in the Preakness at Pimlico one week later, but Pensive prevailed by three-quarters of a length over juvenile champion Platter. Farther up the track was future Hall of Famer and all-time leading money winner Stymie.
Favored to complete the Triple Crown sweep in the Belmont Stakes three weeks after the Preakness, Pensive held a one-length lead at the quarter pole but could not win a prolonged stretch battle with classic newcomer Bounding Home, who upset the 1 1/2-mile “Test of the Champion” at odds of 16-1. As would be the case with Real Quiet’s jockey Kent Desormeaux decades later, some pinned blame for the loss on McCreary believing he had made his bid for the lead too soon.
“I guess he was too anxious to please the public,” Jones said of McCreary.
Not only did Calumet have the best three-year-old colt in the country, but also the best filly. Twilight Tear perhaps could have been the horse to represent the stable in the Triple Crown if Pensive had not emerged as the preferred hopeful that spring. After a season-opening loss at Hialeah, Twilight Tear would reel off 11 straight wins before meeting defeat. Among these were facile victories in the Pimlico Oaks, Acorn Stakes, and Coaching Club American Oaks.
An intramural showdown between Pensive and Twilight Tear had been talked up even before the Belmont. When the Calumet stable took up its preferred summer residency in Chicago, there wasn’t long of a wait for that to happen.
Six days after Twilight Tear extended her winning streak in the Princess Doreen Stakes at Washington Park, Pensive made his first post-Triple Crown appearance in the 1 1/8-mile Stars and Stripes Handicap on July 4. Though favored to beat eight older rivals, he conceded a significant amount of weight on the scale to all of them and hung badly after reaching contention on the final turn. He finished fourth, beaten more than seven lengths.
Just two days later, Pensive and Twilight Tear met for the first time in the seven-furlong Skokie Handicap. Coupled in the wagering, Twilight Tear led wire-to-wire to win by 1 1/2 lengths with Pensive faring no better than fifth. The colt was no match for his stablemate again later in the month in the 1 1/4-mile Classic Stakes (later known as the Arlington Classic). Twilight Tear led throughout to win by two lengths, with Pensive 6 1/2 lengths behind in third.
Their paths diverged from this point, but Pensive’s late-season crumbling continued for the duration of the Washington Park meet. Fourth in the one-mile Dick Welles Handicap in his next start, he was then a badly-beaten fourth in the American Derby. Still believing a turnaround was possible, bettors made Pensive the 5-2 favorite to beat older rivals in the Washington Park Handicap on Labor Day, but again the Calumet colt proved ineffective in a sixth-place finish. Pensive was retired soon after, ostensibly due to a tendon issue.
By Jimminy, who had bypassed the Triple Crown, won five of his final six stakes appearances of the season, including a six-length romp in the American Derby in his only meeting with Pensive. That was sufficient evidence for voters to give the three-year-old championship to By Jimminy over a colt that had nearly won the Triple Crown and had also beaten older horses early in the season.
Twilight Tear encountered some bumps in the road late in her campaign as well, but finished things off with a six-length win in the Pimlico Special over Devil Diver, the champion older male. She was voted Horse of the Year, the first filly to earn the honor. Meanwhile, in a poll of Associated Press sports editors, Pensive was voted the seventh biggest “Flop of the Year” in sports for 1944, finishing in a tie with the Brooklyn Dodgers and the Chicago Cubs.
Pensive died prematurely at the age of eight in May 1949, only a few weeks after a son from his first crop, Ponder, won the Kentucky Derby. Ponder himself sired a Kentucky Derby winner, Needles, in 1956. The only other three-generation grouping of Kentucky Derby winners has been Reigh Count (1928), Count Fleet (1943), and Count Turf (1951).