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​The Toboggan ignited Richard Migliore’s desire to become a rider

by Ryan Martin

When asking an aspiring jockey what races they dream of winning, marquee events like the Kentucky Derby and Belmont Stakes often top the list. But Brooklyn-native Richard Migliore had his heart set on winning the Toboggan, which will celebrate its 129th renewal on Saturday, 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. 

While trips to the Big A were instrumental in shaping Migliore’s dreams of becoming a jockey, it wasn’t the Wood Memorial or even any Triple Crown race that encouraged Migliore to pursue his goals - it was the Toboggan.

Migliore’s connection with the historic sprint began in 1976 when Harbor View Farm’s homebred Due Diligence captured the Toboggan by 4 3/4-lengths under Hall of Famer Jorge Velasquez. 

“My father and I would catch the train right off Avenue U in Brooklyn. There was a bakery that had the best Boston cream donuts right by the station,” 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, piloting Jerome Moss’ Fighting Fit to a narrow victory over regally-bred stakes-winner Entropy for the late Hall of Famer Bobby Frankel. 

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 aboard the son of Majestic Prince, finishing 12th in the first leg of the Triple Crown won by Spend a Buck. 

“I can vividly remember being on the train telling my father I was going to win the Toboggan Handicap. It was about nine or ten years after the conversation, but it was definitely on my mind,” Migliore said. “It felt really cool. A couple of months later I won the Wood Memorial. I just remembered being that kid staring at the wall of all the pictures of Wood Memorial winners. I could have told you every trainer, owner, and jockey that had ever won it. Aqueduct has always been meaningful to me and obviously the Toboggan was important because some of my first memories are attached to it, knowing that I wanted my life to go in the direction it went.”

Migliore said winning the Toboggan aboard a Frankel-trained horse was extra special as the Hall of Fame trainer was a first cousin of his former teacher, Joe Rodlitz.

“Fighting Fit was a big deal because Bobby Frankel was shipping a horse from California and tapping me to ride him,” Migliore said. “Ironically enough, my sixth grade social studies teacher Mr. Rodlitz was Bobby Frankel’s first cousin. I remember one day he caught me reading a racing form in class and made me stay after class. I thought I was in trouble. But then he told me who his cousin was, which was really cool.” 

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] for trainer Rick Schosberg. 

“What a cool horse,” Migliore said of the multimillionaire who raced until age 9. “I got him later in his career. In 2002, it was a prep for the Carter and he ended up winning the Carter as an 8-year-old. Winning a Grade 1 as an 8-year-old was just remarkable.” 

The following year, Affirmed Success arrived at the Toboggan off a third-place finish as the beaten favorite in an Aqueduct allowance race. Migliore, who said he was critical of his own ride in the allowance effort, was named back on the horse and guided him to a win in the 2003 Toboggan. 

The win marked the final career victory for Affirmed Success, who produced triple-digit speed figures in all but 4-of-42 starts. 

“Rick Schosberg had been so supportive and gave me confidence,” Migliore said. “People don’t realize that when a jockey makes a mistake, they’ll never make that mistake again if they’re left on the horse - not if they’re any kind of a rider. So, him leaving me on the horse and being rewarded with another Toboggan was like redemption for a ride I wish I could have had back the start before.”

Schosberg said Migliore and Affirmed Success developed a strong bond.

“To win the Toboggan twice at eight and nine was really special and the two of them had a really great relationship,” Schosberg recalled. “When we put him on the horse the first time, they really got along. The horse had a tremendous personality, like Richie does. Sometimes, he would be warming up before a race and just stare at an airplane. I told Richie, ‘He’s trying to figure out how that works’. He was a smart horse. He wasn’t just looking at it, he was trying to figure out how something flies while warming up for a Grade 1. The three of us were a little long in the tooth, but it was fun.”

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 [1997], Wouldn’t We All [1999] and Kazoo [2006] to Toboggan wins. 

Migliore would usually stay in New York for the winter rather than heading to warmer climates to ride. He attributed his success in the Toboggan to his familiarity with the Big A oval. 

“I always liked to stay in New York. First, I’m a native New Yorker. Second, I have kids and when I was riding, I didn’t want to move them around too much and disrupt their lives,” Migliore said. “Riding at Aqueduct was great. The purses were great, you’re done by 4:30 or 5:00 and you can go home and have dinner with your family. It was the perfect balance of professional and personal life.”

The Toboggan isn’t the only race in New York with sentimental value for Migliore. He grew up in the Gravesend area of Brooklyn and won the neighborhood’s namesake race at Aqueduct in 1997 aboard Royal Haven in a dead heat with Stalwart Member. 

“I won that race which I thought was pretty cool, and then I won the Brooklyn twice and I grew up in Brooklyn,” Migliore said of his Brooklyn Handicap scores with Iron Deputy [2003] and Seattle Fitz [2004]. “Those things are not lost on me. I appreciate them a lot.”

Through Migliore’s outstanding riding career, he won the Mike Venezia Award in 2003 and the George Woolf Memorial Award in 2008, the same year he rode Desert Code to victory in the Breeders’ Cup Turf Sprint. 

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.”