Frank Calabrese's journey in the racing world is a remarkable one. Starting from a young age, he made his first bet at a bookie joint and was instantly hooked. This small bet would lead him to become one of Chicago racing's all-time greats.

Unprecedented Achievements

Calabrese went on to achieve remarkable feats. He tied for the lead in winners at Arlington International Racecourse in 2000 and continued to win more races there every year through 2010. His 74 triumphs in 2007 set a track record, a feat that is still talked about in the racing community.His ownership of Dreaming of Anna was another significant milestone. Not only did he own the filly, but he also bred her in honor of his beloved deceased sister. Dreaming of Anna was selected as North America's 2006 champion 2-year-old filly, a title that brought him great pride.Calabrese's horses also had success in other major races. Silver Maiden won the Grade I Frizette at Aqueduct in 1997, Exclusive Praline triumphed in the Grade II Ohio Derby at Thistledown in 1994, and Fight for Ally won the Grade III National Jockey Club Handicap at Hawthorne Race Course in 2003. These victories added to his already impressive resume.

Claiming Horses and the Team

Claiming horses were the backbone of Calabrese's operation. He always credited his longtime trainer, Wayne Catalano, and bloodstock agent Steve Leving for their roles in his success. Despite sometimes tempestuous relationships, they worked together to achieve great things.Calabrese was quoted as saying, "It's all about winning, and Steve finds horses that Wayne can win with. I never tell Wayne what to do with a horse; if I don't do what he says, I'm making a big mistake." This shows his trust in his team and their ability to deliver results.

From Beginnings to Success

Calabrese's story began when he grew up near Halsted and Taylor streets in Chicago's Little Italy. His parents were of modest means, and he started working odd jobs as a teenager, earning $33 a week. He would give most of the money to his mother and keep only $3.From these humble beginnings, he ventured into betting on horses at Chicago-area tracks. He got to know Dave Feldman and bought his first horse in 1963. Although the horse was not successful, it marked the beginning of his journey in thoroughbred ownership.Later, he got into harness racing and owned about 50 standardbreds at one time. But it was his return to thoroughbreds in the 1980s, thanks to Rob Marcocchio, that truly launched his racing career.

Financial Success and Legacy

Calabrese's success in racing was not only about the wins but also about the financial resources he amassed. He founded FCL Graphics in 1973, a Harwood Heights commercial printing shop that grew into a multimillion-dollar company. He sold it in 2004 and used the funds to invest in his racing empire.During his three decades as an owner, his horses ran in 6,180 races and were victorious in 1,853. His career earnings exceeded $34 million, and he was among the top five owners in North America eight times.Even after leaving Arlington and moving to Gulfstream Park, his involvement with racing continued until the last horse he owned was claimed during the 2023-24 meeting at the Fair Grounds. His legacy in the racing world will always be remembered.Calabrese was a complex man. He could be contentious at times but was also charismatic and generous. His attorney, Jeffrey Bunn, called him "an extremely nice man — very hard-nosed but as honest as the day is long." Jockey agent Robbie Ebanks remembered him as "one of the most dynamic characters I have met — a truly unique man."Trainer Wayne Catalano recalled, "Frank was a great man, he helped everybody. He loved betting, he loved Arlington, he loved racing his horses and he was all about winning."In conclusion, Frank Calabrese's story is a testament to the power of determination and hard work. From his humble beginnings to his status as one of Chicago racing's greats, his legacy will continue to inspire future generations of racers.