“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.