Three Generations Of Great: Starting Something Special

1944 Kentucky Derby winner Pensive
Pensive after winning the 1944 Kentucky Derby. Churchill Downs Racetrack.

The long history of the Kentucky Derby is woven with colors: the cascade of red roses over a winner’s shoulders, the rainbow of carefully chosen clothing adorning the throngs in attendance, the (sometimes) blue skies that celebrate springtime in the Bluegrass. As the horses parade from paddock to post, their riders greet the crowd clad in the silks of each owner, stars and stripes and shapes telling the stories that brought them to the Derby. Some symbolize lifelong friends buying into a dream, others, the celebrated history of a multi-generational investment.

The devil red and blue of Calumet Farm is iconic among these, adorning eight winners of the Kentucky Derby. In the 1940s, Warren Wright’s Pensive started another multi-generational dominance of America’s most famous race, and, two generations later, helped expand breeding in another state. From the Bluegrass to the Sunshine State, let’s learn more about another Derby dynasty, where deep closers became a familial calling card.

Pensive, the First

When a weanling Hyperion arrived at Side Hill Stud, he boasted a large pedigree: his sire was English Triple Crown winner Gainsborough and his dam, the notable broodmare Selene, had been the best filly of her crop at age two and three. Hyperion himself, though, was so small that he needed a makeshift lower manger in his stall. Like his dam, this son of Gainsborough never grew as large as his peers, but he could outrun them with no trouble at all, winning two English classics at age three. As a sire, he stood even taller. When Lord Astor offered three of his mares to Arthur Hancock, he threw in a season with Hyperion and Hancock took him up on it. One of those mares was Penicuik II, who was imported in foal to Hyperion to the United States.

When those three mares arrived in Kentucky, Warren Wright of Calumet Farm took a liking to Penicuik II and purchased her from Hancock in late 1940. So, when she foaled her colt by Hyperion on February 5, 1941, his official breeder of record was Calumet even though Hancock had selected the pairing. Named Pensive, the chestnut colt by all accounts was a taller version of his diminutive sire, with only a smidge of white on his forehead. By the early 1940s, Calumet was coming into its own as a powerhouse in American racing, with Whirlaway winning the Triple Crown in 1941. That 1941 crop of foals boasted not only Pensive, but also Twilight Tear, two-time champion filly and Horse of the Year for 1944. Both would have slow starts at age two, but, at age three, these two would make 1944 another year of the devil red and blue.

Pensive had won a couple of allowance races at age two, with his third-place finishes in the Champagne and the Bowie Stakes his best stakes finishes of 1943. In 1944, he ran seven times before the first Saturday in May, winning three, including a handicap against older horses at Pimlico. In his other four races, Pensive finished either second or third, so it was no surprise that he joined eighteen others at Churchill Downs for the 1944 Kentucky Derby.

With jockey Conn McCreary, Pensive started from post position four and ran much of the race just behind the front runners, with little change in position until the final turn. McCreary saw a chance to move to the rail and ducked Pensive through, picking off tiring horses one by one. He zipped past Stir Up and Broadcloth in the stretch to win by four and a half lengths, giving Calumet its second Kentucky Derby. A week later, he duplicated that performance at Pimlico, winning the Preakness over Platter by three-quarters of a length. On the precipice of the Triple Crown, the second for Calumet in less than five years and on the heels of Count Fleet’s the year before, Pensive traveled to Belmont Park for the third leg of the Triple Crown.

McCreary moved Pensive into the lead earlier than usual in the mile-and-a-half Belmont Stakes, with the Derby-Preakness winner moving into the front runner position on that final sweeping turn. In the stretch, he was in front by a length when the late-running Bounding Home mounted a furious drive for the finish and managed to catch Pensive in the race’s waning yards, winning the Belmont by a half-length. Of the two near-misses to that point, neither Bold Venture nor Burgoo King had started in the Belmont, so Pensive became the first Kentucky Derby-Preakness Stakes winner to lose the Belmont Stakes and the Triple Crown. After the Belmont, Pensive would lose his remaining starts in 1944, and, at year’s end, was not voted the champion three-year-old colt of the year, with that honor going to By Jimminy, who had won the Dwyer, the Travers, and the Lawrence Realization. Pensive was retired to stud at the end of 1944, his poor showing in his final races owed to a tendon injury that arose after he struck himself during the Preakness.

At stud, Pensive appeared to have a stellar career ahead of him, siring forty-one winners and seven stakes winners from fifty-three foals, but met an early end from a twisted intestine at age eight. From his first crop came another Calumet homebred that would wear roses, a colt named Ponder.

Ponder after winning the 1949 Kentucky Derby. Pensive, Needles
Ponder after winning the 1949 Kentucky Derby. Churchill Downs Racetrack.

Ponder, the Second

Calumet Farm’s Miss Rushin was supposed to be a racehorse first. She had the pedigree for it, sired by Blenheim II and out of a Sir Gallahad III mare, but an ankle injury prevented this homebred from ever facing the starter. Instead, she became a part of the farm’s broodmare band, visiting Pensive during his first season at stud. On April 14, 1946, Miss Rushin foaled a brown colt with two hind socks and a wee smidge of white on his forehead. Wright named him Ponder.

At two, Ponder lost all four of his races, Hall of Fame trainer Ben Jones attributing his winless status to the colt’s running style. As a closer, Jones knew Ponder would have won more races had he just started running a bit earlier. With just over two weeks between his last start at two and his first start at three, this son of Pensive’s 1949 season was more a continuation of his two-year-old season; he finally broke his maiden in that first race of the year, winning by three-quarters of a length. He won two of his next seven starts with three second-place finishes, including in the one-mile Derby Trial the week before the Kentucky Derby. It was that race, his first at a mile, that showed Jones that Ponder could benefit from more distance. On May 7, 1949, Ponder joined thirteen others in the starting gate for the 75th Kentucky Derby.

True to form, Ponder and jockey Steve Brooks lingered toward the back of the field early, with Fred Hooper’s Olympia winging away on the lead. As the field entered that final turn, Brooks set his mount down for the drive, picking off tiring horses one by one. He was sixth at the one-mile mark and then third entering the stretch, passing a tired Olympia to win by three lengths. At 16-1, he was a long price for a Calumet horse, and, as the fourth of their eight Derby winners, he would be the last one sent off at such odds. A week later, in the Preakness, he started his run too late and never factored, losing to Capot, who had finished second in the Derby. Less than a week later, the news that Pensive had succumbed to a twisted intestine broke, making Ponder’s Derby win even more meaningful. Not only was he a second-generation Derby winner, but he would also become Pensive’s most successful offspring.

The Belmont was more of the same. Jockey Ted Atkinson put Capot on the lead early, rating the son of Menow, and, when Ponder made his late move, was able to hold off the Derby winner. Ponder followed up his Triple Crown campaign with victories in the Arlington Classic, the Jockey Club Gold Cup, and the Lawrence Realization. At four, he defeated Citation in the San Antonio Handicap, and won the Arlington Handicap and the Tanforan Handicap among his wins in 1950. Ponder retired to Calumet Farm where he stood stud for eight years until his early death from a twisted intestine in 1958.