Even though Middleground won two of the three jewels of the Triple Crown in 1950, most of the attention that year centered on Hill Prince, who was supposed to sweep the series with ease. The horse had won 6 of 7 starts at age 2 and had won the Wood Memorial.
Middleground was an afterthought, a horse with bad ankles who had finished second five times that year – three times to Hill Prince, who had dominated the early prep season. So when Middleground, an 8-1 choice in the Derby, passed a trapped Hill Prince in the homestretch and beat him by 1 1/4 lengths, everyone asked, “What happened to Hill Prince?”
The son of 1936 Derby and Preakness winner Bold Venture, Middleground, ridden by 16-year-old apprentice jockey Bill Boland, ran only 1/5 of a second slower than Whirlaway’s 2:01 1/2 record for the Derby. But instead of talking about his amazing victory, many fans pointed to Hill Prince’s jockey, Eddie Arcaro, as the cause of the favorite’s demise. Horse racing experts alleged that he had pulled up Hill Prince twice during the race, which may have cost him enough time to take the Derby.
Beaten in the Preakness
Despite his second-place finish, Hill Prince was made the bettors’ favorite again and got his revenge in the Preakness, as Arcaro turned him loose at the end of the backstretch. Middleground followed him but didn’t have the speed to catch him that day. Hill Prince went on to win by a commanding five lengths over his rival in 1:59 1/5, the fastest Preakness ever on a muddy track.
The Belmont shaped up to be the rubber match between the two, and Hill Prince was the prohibitive favorite. Arcaro made sure that his horse was in command, coaxing Hill Prince to a 1-1/2 length advantage over Lights Up after a blistering mile in 1:37 – equaling Citation’s mark through the same distance. He continued that pace, running 10 furlongs in 2:02 1/5 – the fastest ever for a Belmont – as Middleground plodded along in fourth place.
The young jockey Boland was watching, though, and as Hill Prince began to show signs of tiredness, he and MIddleground made their move and caught Lights Up with 50 yards to go, winning the Belmont by one length. Hill Prince, spent, finished a disappointing seventh.
Middleground became only the fifth horse to capture both the Derby and the Belmont. But despite his impressive performances in the two races, Hill Prince was named Three-Year-Old Male Champion. The horse went on to capture eight stakes races that year, including the American Derby and Jerome Handicap. Middleground, meanwhile, finished 6-6-2 in 15 starts, including a baffling 10th-place finish in the Jerome Handicap.
At stud, he was not able to produce another Derby winner like his sire did. He passed along his trait for bad ankles, and he was not very fertile. He sired 101 winners but only 7 stakes winners from 130 foals.