Troutt is the 13th Triple Crown winner, and has won the Kentucky Derby twice, the Preakness Stakes once, and the Belmont Stakes three times. He is the owner of Justify, the 13th Triple Crown champion.
Troutt, a big Republican supporter, has contributed to American Crossroads which is a US Super PAC that raises funds from donors to advocate for certain candidates of the Republican Party. Preston Troutt, Troutt's son, has likewise donated to Republican candidates.
Troutt struggled financially as a child and worked extremely hard to get to where he is now.
Troutt was born in Mount Vernon, Illinois, in the United States in 1948. His father was a bartender at the time. He was the eldest of three brothers and sisters. Troutt attended Mt. Vernon Township High School and went on to Southern Illinois University, where he earned his bachelor's degree in 1971.
Coming from a poor background, he was determined to overcome the challenges and support his family and become wealthy. Due to this, he started working at a very young age in order to support his family to get extra bucks.
As a child, he was introduced to horse racing by his uncle and fell in love with it right away. He attended races at Churchill Downs while in college and was in the audience when the great Secretariat won the Kentucky Derby.
Troutt chose to follow his ambitions after graduating from college and opened his first horse farm, Landview, in eastern Nebraska, in the early 1980s. However, it took him more than a decade to become a millionaire and be able to devote himself fully to horses and the ownership of thoroughbred racehorses.
Troutt and his colleague Steve Smith started Excel Communications, a long-distance telephone business, in 1988 with a history in network marketing. Excel Communications was one of the fastest-growing corporations in the United States, not just in its field. In 1996, he went public with the company. It was the newest firm to join the New York Stock Exchange at the time.
The corporation had more than a billion dollars in revenue in 1998, a decade after its establishment. Troutt sold the company to Teleglobe for $3.5 billion the following year. That year, he became a billionaire for the first time. One of his boyhood fantasies came true when he was able to flee his surroundings and no longer be destitute.
Troutt was offered the chance to purchase Prestonwood, a 400-acre horse farm in Kentucky, in 2000. He jumped at the chance to fulfil yet another of his youthful aspirations. He changed the name of the horse farm to WinStar Farm and set out to make it one of the greatest horse breeding and racing farms in the area.