Born: Nov. 4, 1928

Birthplace: Chicago, IL

Residence: Chicago, IL

Family: Sons Frank, Carmen and Lewis

First Winner: Appealing Ring

Started Ownership: 1981

Tampa Bay Downs Trainer: Rick Slomkowski

Frank C. Calabrese’s first bet, 50 cents at a bookie joint, paid $21 and provided him with what was then a week's pay. Calabrese raced Standardbreds for 14 years before switching to Thoroughbreds about 26 years ago. His first Thoroughbred, Appealing Ring, won her first race for him, but his luck cooled after that; Calabrese says that he once paid $190,000 for a horse, and “he turned out to be a real pig.” 

Calabrese has been in the business for about a quarter of a century and ranks as a true character at the track. He has experienced great success, and among the top horses currently in his stable is Dreaming of Anna, who is named after his late sister; the filly defeated males in Woodbine's Summer Stakes and won the Breeders’ Cup Juvenile Fillies.  Dreaming of Anna raced against eventual Florida Oaks winner Cotton Blossom in the Breeders’ Cup Juvenile Fillies; the pair later rematched in the 2007 Kentucky Oaks.