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Pensive became the second of eight Kentucky Derby winners to be bred and owned by Calumet Farm; he was also the third of six winners to be trained by Ben Jones.

Pensive was actually bred in England and sent to the United States in utero. His dam *Penicuik II was sold along with two other mares to Claiborne Farm owner Arthur B. Hancock. The mare’s owner, Lord Astor, made part of his offer that one of the mares could be bred to Epsom Derby winner, Hyperion. The mare Penicuik II was chosen and bred before the mares were sent to Claiborne. Warren Wright of Calumet liked the mare when he saw her, wanting her for his broodmare band. A deal was made with Wright buying her prior to her foaling Pensive, which by the official rules at the time, made Wright’s Calumet Farm, the breeder.

Hancock also had a part in the producing of Pensive’s son and Kentucky Derby winner, Ponder. In 1922, Hancock purchased a yearling filly named *Erne while overseas. *Erne produced the mare Miss Rushin, who ended up being the dam of Ponder, her first foal.

Pensive didn’t have the greatest of 2YO campaigns, after winning his first two starts; he then would finish 3^rd in the Champagne and Oden Bowie Stakes, as well as 4^th in the Futurity in his other three starts.  He did however start off his 3YO season by winning the Rowe Memorial Handicap. Pensive had two seconds after that, with Jones unsure of his Derby chances.  It wasn’t until he saw the horses that were looking to contest the race that he decided to take a chance.

In the second of the “Street Car Derbies”, which saw around 60,000 attend, Conn McCreary would take the reins on Pensive in the field of sixteen. The favorite was Stir Up, ridden by Eddie Arcaro, while another challenger was Broadcloth who was ridden by George Woolf. Pensive ran behind these two leaders as they turned for home into the stretch. Woolf, who was riding inside of Stir Up with a bit of a lead, believed Arcaro was the only one that he had to beat, so he took Broadcloth wide to throw off Stir Up and Arcaro. Unfortunately for those two riders, going wide opened up the rail, allowing McCreary to pull Pensive to the inside. The combo pulled ahead, winning by an easy 4 ½ lengths in a time of 2:04 1/5 over a good track.

After winning the Derby, he went on to win the Preakness, although in the process, he would run down during the race, meaning that he irritated the area around the back of his hooves. This threw off his training prior to the Belmont, although he still nearly won, just beaten by 16-1 shot, Bounding Home, by half a length. Pensive was the first horse to win the Derby and Preakness, yet lose the Belmont.

He never won another race, due to a bowed tendon that he received, never quite recovering. Pensive retired to Claiborne, where he stood until his early death in 1949, the same year that his son Ponder would win the Kentucky Derby. Even though he had a short stud career, it was impressive, siring 41 winners, six of them stakes winners, from 53 foals. Pensive started the second set of three-generation winners. His son Ponder would go on to sire 1956 winner, Needles. Pensive is buried in the Calumet cemetery.

(Horse Shoe courtesy Kentucky Derby Museum archives)