When aspiring jockeys dream of Winning races it’s usually marquee events like the Kentucky Derby and Belmont Stakes that top the list.
But Brooklyn-native Richard Migliore had his heart set on Winning the Toboggan Handicap, which will celebrate its 129th edition, this weekend at Aqueduct Racetrack.
Migliore, 57, was a multiple Grade 1-Winning jockey with 4,450 career Victories and earnings in excess of $160 million through a riding career that spanned three decades.
Today, he serves as a racing analyst for the NYRA-produced America’s Day at the Races.
As a kid, Migliore accompanied his father on frequent trips to Aqueduct where he would admire pictures on the second floor wall of the horses who had Won the Wood Memorial.
Migliore recalled. “My father took me to Aqueduct one day in 1976 to watch the Toboggan. On the train ride home, I remember telling my father, ‘Pop, I’m going to be a jockey and I’m going to Win the Toboggan Handicap one day.’
“I already had it in my head that I wanted to be a jockey,” Migliore continued. “I grew up in Brooklyn maybe nine miles from Aqueduct. I didn’t think about the Kentucky Derby, that might as well have been Mars. But Aqueduct was in my backyard pretty much and the Toboggan had meaning to me.”
Migliore proved to be a man of his word. In 1981, the 17-year-old was the leading rider on the NYRA circuit and awarded honors for Outstanding Apprentice Jockey in only his second year of riding.
But it wasn’t until 1985 that Migliore achieved his childhood dream of Winning the Toboggan, riding FIGHTING FIT to a narrow Victory.
Migliore expanded on his success at Aqueduct that winter by guiding ETERNAL PRINCE to Victories in the Gotham and Wood Memorial en route to his first Kentucky Derby mount.
Unfortunately ETERNAL PRINCE finished 12th out of thirteen starters, in a Derby Won by SPEND A BUCK.
Migliore went on to Win the Toboggan five more times in his 30-year riding career, including back-to-back Wins aboard fan favorite AFFIRMED SUCCESS [2002-03].
With a total of six Toboggan Victories, Migliore is the Winningest jockey in the race’s rich history. In addition to FIGHTING FIT and AFFIRMED SUCCESS, Migliore also rode ROYAL HAVEN , WOULDN’T WE ALL  and KAZOO  to Toboggan Wins.
Crowned as the leading rider in New York in 1981 and 1985, Migliore also has either Won or tied as leading rider at 10 different NYRA meets. But the veteran rider said few races connect to him as closely as his affection for the Toboggan.
“It has personal meaning to me since it was a race that helped fuel or fan the flame that helped me become a rider,” Migliore said. “There’s other races in New York that I have the most Wins in as well. But personally, the Toboggan means a lot to me.”