Pensive was a bright chestnut thoroughbred racehorse that in 1944 came closer than any other horse at the time to winning the U.S. Triple Crown. He was also the first to win the first two legs and then lose the third. A son of England's Hyperion, out of Penicuik II, Pensive, ridden by Conn McCreary, won the Kentucky Derby going away by four and a half lengths. A week later, he took the Preakness. That year, the Belmont, had upped its purse to $50,000. Pensive was in the lead when bounding Home inched by to take the race by less than half a length. Pensive was brought to the United States still forming in his mother's womb by Arthur B. Hancock, who then sold the mare to the owner of Calumet Farm, Warren Wright.
Wright had inherited Calumet from his father, William Monroe Wright, president of the Calumet Baking Powder Company. In time, Warren Wright was also president of the baking powder company, and he took it to the financial heights of the business world. When he also took over Calumet in 1931, he sold off the trotters his father favored and began buying Thoroughbreds for flat racing. Under Wright, Calumet enjoyed years of racing dominance. Pensive began his training under Calumet's future Hall of Fame trainer Ben A. Jones. At two, Pensive raced five times, winning twice.
His three losses all came in stakes races. At three, he ran a checkered season, winning and losing fairly equally. He beat older horses in the Rowe Memorial Handicap, but lost to an older horse, Tola Rose, in the Bowie Handicap. Tola Rose had defeated Whirl away. Following his loss in the Belmont, Pensive lost all eight of his final starts. At this point he was retired to stud, producing the winner of the 1949 Kentucky Derby, Ponder. He died in 1949, just after his son won the Derby. Pensive is buried at Calumet Farm.