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Middleground was the second Kentucky Derby winner for owner Robert J. Kleberg’s King Ranch in Texas. Like Assault he was by 1936 winner Bold Venture. Out of the winning Chicaro mare, Verquenza, the chestnut colt got his name due to his always being ranked in between two of Bold Venture’s other sons on the ranch, Air Lift and Beau Max.  Chicaro was one of Kleberg’s initial thoroughbred purchases The colt was sent to Kleberg’s trainer, Max Hirsch, for his groundwork.

As a 2YO, Middleground won his first start at Belmont in May. Two months later he would suffer his only loss of the year when he finished third in the Arlington Futurity. He would win two overnight sprints before taking on the Hopeful, where he would provide his connections with a powerful 6 length victory. After developing osselets, his freshman undertaking was finished. Starting out his 3 year-old season, Middleground would finish second in his first four starts, losing to Hill Prince in the Wood Memorial prior to a second in the Derby Trial where he loafed over a sloppy track.

The Kentucky Derby was Middleground’s fifth start in 25 days, yet it was his first victory of the year. Piloted by apprentice jockey Bill Boland, Middleground raced close to the pace, just tracking the leaders, and saving ground throughout.  Once the pair reached the stretch, Middleground put in a punishing drive to take the lead, outlasting Hill Prince and Eddie Arcaro by a length and a quarter in a time of 2:01 3/5 over a fast track, just 1/5 off of Whirlaway’s record. In the winner’s circle, trainer Hirsch paid off a $100 wager that he had placed with Kleberg. He had bet that Middleground wouldn’t win the race, possibly believing that his stablemate On the Mark would take the race. The 18 year-old from Texas, Bill Boland, in winning, became only the second apprentice jockey to win the Kentucky Derby, following Ira Hanford, who rode Middleground’s sire, Bold Venture, to victory in 1936. In the Preakness and Withers, Middleground would finish second to Hill Prince, before taking control in the stretch and turning the tables in winning the Belmont. The Belmont would be the colt’s last victory as he finished 3rd in both the Leonard Richards Stakes and Jerome Handicap, before fracturing the sesamoids in his right foreleg while training.

Middleground would survive the injury due to his intelligence along with his calm demeanor. The colt learned to lie down and get up without touching his injured foot to the ground. Though he was through racing, his sophomore endeavor earned him the 3YO Champion Colt as well as Horse of the Year honors. The following year Middleground entered stud at his owner’s King Ranch, where he was known as a “shy breeder”, only siring 130 foals out of 18 crops, however he had a good number of stakes winners, including a trio of stakes winning fillies. His Reseca would win the CCA Oaks, Here and There claimed victory in the Alabama, and Ground Control would score in the Acorn. Middleground would pass away in 1972, being buried at King Ranch.

(Print courtesy of Kentucky Derby Museum archives)