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By the early 21st century, the economics of thoroughbred horse racing in the United States was backwards - owners invested about four times as much money into the sport than the total amount of purse money available. Owners raced their horses as early as possible, and for as short a time as possible to prove that they were valuable for breeding - then sold them to breeding operations. The industry relied heavily on new entrants who had money from outside horse racing to buy and race their foals. Stonestreet Farms was founded by Jess Jackson, a billionaire wine entrepreneur, who invested more than $200 million in the sport. Unlike most in the horse racing business, Stonestreet was involved in both training and racing horses and in breeding. Two of its horses, Curlin and Rachael Alexandra, won the coveted North American Horse of the year for three consecutive years, from 2007-2009. Both later became part of Stonestreet’s breeding operation. This case discusses the challenges facing owners and breeders in the North American thoroughbred racing industry. It can be used as a companion case to 'Del Mar Racetrack: Reinventing the Horse Racing Fan Experience', which focuses on the industry from the perspective of race tracks.