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C O N S T E L L A T I O N C O N S T E L L A T I O N WinStarFarm.com The Jeff Ruby Experience 54 Long before Ruby was a colorful and entertaining restaurant entrepreneur, he had a love for horse racing. He fell for the sport while growing up on his own during an unconventional childhood. "I ran away from home when I was 15," he said. "I raised myself through high school. I didn't have parental guidance or direction. I lived in a rooming house with senior citizens, where I had an 8x10 room, and we all shared one bathroom. That's how I grew up in New Jersey. My love of horse racing goes back to when I was in high school. I would hang out at Monmouth Park in my spare time." In 1963, as a freshman, Ruby offered his classmates a chance to bet on the Kentucky Derby. All they had to do was give him $2, and if they picked the winning horse, he would pay them back whatever the horse officially paid. "I told all these kids at Neptune High School in New Jersey if they wanted to bet on the Kentucky Derby, give me $2 and take the horse you want to win," he said. "Thirty or 40 kids gave me money. The horse that won was a horse named Chateaugay, which no one had because he was a long shot. If anyone would have had won, I would have been broke, but instead I made a little money." That wasn't the only time Ruby taught his classmates about the sport and some of its equine heroes. As a football player, he proudly wore the name Kelso on the back of his practice jersey, much to their bewilderment. "You had to practice, obviously, and you had to get a sweatshirt," said Ruby. "They didn't provide one, so I got a white one to wear over my shoulder pads. I got a magic marker, and my hero back then was Kelso. I put Kelso in big, black letters on the back. The kids didn't know what I was talking about, but I loved that race horse." One summer, Ruby got a job at Monmouth Park, working for Harry M. Stevens. The catering job wasn't glamourous, but it is one that taught him plenty of lessons going forward. "I made minimum wage, and I lost more than that betting on the races while I was walking around the track," Ruby said. "I had to walk from one concession stand to another and count paper cups to make sure that the people working weren't giving away free drinks. If they did, a cup would have been missing. I learned a lot about cost controls that summer." Ruby supported himself with a variety of restaurant-related jobs and graduated from Cornell University. Following graduation, he was hired at a hotel near Cincinnati in 1970. It was there he would eventually begin to build his restaurant empire and become a race horse owner. "I was working in the Holiday Inn as an assistant manager," Ruby said. "A horse trainer came in there, and we became friends. The next thing you know, I started claiming horses through him for $5,000 or whatever I could afford. The first horse to win with me as an owner was named Champagne Princess." As Ruby's career grew, so did his quality of horses, which are often owned in partnerships with friends. Most recently, that includes Dabo, who ran a solid fifth in the cheekily-named Jeff Ruby Steaks (G3) at Turfway Park. The fact Ruby has a race at that particular track is appropriate given his success in nearby Cincinnati. In 1981, Ruby opened his first restaurant, The Precinct, which is now Cincinnati's longest continually-running fine dining restaurant. He followed its success with The Waterfront in 1986, Jeff Ruby's Steakhouse in 1999, Carlo & Johnny in 2001, Jeff Ruby's Steakhouse, Betting on Himself Building an Empire