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“The first bet I ever made was at a bookie joint when I was 11 or 12,” Frank Calabrese once told the Tribune. “I bet 50 cents and got $36 back and I was hooked.”
Calabrese went on to become one of Chicago racing’s all-time greats, a thoroughbred owner who tied for the lead in winners at Arlington International Racecourse in 2000 and then won more races at the now-defunct track every year through 2010, an unprecedented accomplishment. His 74 triumphs in 2007 set a track record.
Calabrese died Nov. 4, his 96th birthday and — as fate would have it — the date of his greatest triumph in racing: Dreaming of Anna’s front-running victory against 13 opponents in the 2006 Breeders’ Cup Juvenile Fillies at Churchill Downs.
Not only did Calabrese own Dreaming of Anna, but he also had the distinction of breeding the filly named in honor of his beloved deceased sister, Anna. Dreaming of Anna was selected as North America’s 2006 champion 2-year-old filly.
Calabrese had other horses that went to the winner’s circle after major races, most notably Silver Maiden in the Grade I Frizette at Aqueduct in 1997, Exclusive Praline in the Grade II Ohio Derby at Thistledown in 1994 and Fight for Ally in the Grade III National Jockey Club Handicap at Hawthorne Race Course in 2003.
However, claiming horses were the bread and butter of Calabrese’s operation, and he unfailingly cited his longtime trainer, Wayne Catalano, and bloodstock agent Steve Leving for their roles in his success story, even though the relationships sometimes were tempestuous.
“It’s all about winning, and Steve finds horses that Wayne can win with,” Calabrese was quoted as saying in a 2003 Tribune story. “I never tell Wayne what to do with a horse; if I don’t do what he says, I’m making a big mistake.”
During his three decades as an owner, Calabrese’s horses ran in 6,180 races and were victorious in 1,853. His career earnings exceeded $34 million. He was among the top five owners in North America eight times.
“When I first got into racing, I couldn’t stand the smell of horses,” Calabrese reminisced during his heyday at Arlington. “Now they smell like perfume.”
In 2011 Calabrese left Arlington and moved his stable headquarters to Gulfstream Park in suburban Miami. He divided his time between a home there and in Park Ridge, where he resided in hospice at the time of his death. His involvement with racing ended when the last horse he owned was claimed during the 2023-24 meeting at the Fair Grounds in New Orleans.
No relation to the deceased convicted Chicago mobster with the same first and last name, Calabrese could be contentious at times. He did not suffer fools.
But he also was charismatic and generous, and in a 2005 Tribune story by Jon Yates, his attorney, Jeffrey Bunn, called Calabrese “an extremely nice man — very hard-nosed but as honest as the day is long.”
Jockey agent Robbie Ebanks remembers him as “one of the most dynamic characters I have met — a truly unique man.”
“Frank was a great man, he helped everybody,” Catalano recalled. “He loved betting, he loved Arlington, he loved racing his horses and he was all about winning.”
The financial resources that enabled the man who grew up near Halsted and Taylor streets in Chicago’s Little Italy to establish his equine empire came from FCL Graphics, a Harwood Heights commercial printing shop he founded in 1973. He expanded it to include direct mail, web and marketing services, and it was a multimillion-dollar company when he sold it in 2004.
“I’m proud for a man with no formal education to have accomplished what I have accomplished,” he told Yates.
Calabrese’s parents were people of modest means who rented a two-bedroom apartment. As a teenager he earned $33 a week working odd jobs and would keep only $3, giving the rest to his mother.
From his beginning venture as a boy at “a bookie joint” in his neighborhood, Calabrese gravitated to betting on the horses at Chicago-area tracks.
He got to know the late Dave Feldman and in 1963 bought his first horse in partnership with the colorful handicapper/racing columnist at the Chicago American, Daily-News and Sun-Times, who doubled as a thoroughbred owner and trainer.
Calabrese would later say, “The horse was no good.”
Then Calabrese got into harness racing and at one time owned about 50 standardbreds.
“He had a couple of decent ones but nothing earth-shattering,” remembered Peter Galassi, Hawthorne’s longtime track announcer.
In the 1980s, the late northwest suburban bloodstock agent Rob Marcocchio persuaded Calabrese to give the thoroughbreds another try.
The rest is racing history.
Neil Milbert is a freelance writer who covered horse racing and other sports during his 40-year career with the Chicago Tribune.
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