Yonkers: Gregory eyes top prize in three NY Sire Stakes finals

The New York Sire Stakes circuit has been a regular staple of Jeff Gregory's existence for over 20 years. As one of the leading drivers in the Empire State, Gregory would routinely travel from track to track and pick up high-level catch-drives. His ability to handle trotters as adeptly as pacers made him the go-to guy no matter what age, gait or sex.

In recent years Gregory has moved away from a workload that is heavy in driving and concentrated on a small stable based at Vernon Downs. While his New York-sired horses campaigned on the Sire Stakes, he would often find himself in the bike of other leading contenders. On Saturday, Gregory finds himself in a rather different position and one he's never had before. With eight $300,000 New York Sire Stakes championships on the line at Yonkers Raceway, Gregory has three from his stable of just five horses in contention for the big money.

"I've definitely driven more than three horses on these days," Gregory said of the traditional New York Night of Champions that has been converted to the afternoon to accommodate the $1 million MGM Yonkers International Trot on the 11-race program that commences just before noon.

Just reaching the Sire Stakes final these days requires a horse that is versatile enough to race over a multitude of track sizes. In the case of young trotters, it often requires horses maintain their gait going around tight turns while still learning the ropes of racing. Gregory has mastered the art having his horses earning while learning, and it's that kind of approach that has landed him three coveted spots in a short list of horses reaching Saturday's biggest prize.

Gregory and owner Steve Finkelstein (Jesmeral Stable) were fortunate enough to purchase Highway Six late during his 2-year-old campaign. "They were racing him on the New York Fair Circuit," said Gregory, speaking about Highway Six. "I got to drive him in his last two starts as a 2-year-old and thought he was a horse that could definitely race against Sire Stakes company."

A winner in six of his seven starts as a freshman, Highway Six is out of the Cash Hall-sired mare Highway Cash, herself a 19-time winner on the racetrack. Highway Cash is a half-sister to a pair of quarter-million dollar winners, with both Darron Hall and J A T O combining for an astonishing 84 career victories.

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For Gregory, as a sophomore, Highway Six has been consistent and competitive, winning in three of his nine starts and finishing on the board in four others. Highway Six enters Saturday's second race with earnings this year already in excess of $102K and a chance to add to that significantly.

"There's a lot of nice horses in the field," said Gregory about the second race starters. "Ake's (Svanstedt) horse (Read The Room) can leave like a runner. You have AI in there and he's got a lot of class. Noel's (Daley) horse Chapter Geo J has been solid as well."

On the positive side for Gregory is that Highway Six landed the pole position and can leave the gate.

"He should be able to work out a trip and hopefully be right there on the wire," said Gregory, who sees a bright future for a horse that has but 16 career starts heading into Saturday.

"I definitely think he's a future Open Trotter at Yonkers," added Gregory, who, with his years of experience, would certainly know what it takes to succeed at that level. "I'm sure that's what Steve (Finkelstein) would want."

Post position is key in this division and Highway Six finds contenders Chapter Geo J and Read The Room with posts six and eight, respectively.

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Wavy Xavie is another by Met's Hall, she a 2-year-old filly that has yet to win in six starts but has stayed trotting for Gregory and is one of only seven that declared for the $300,000 New York Sire Stakes final for rookie trotting fillies (race four). Waxy Xavie drew post three and could be in line for a decent check.

"It's a good draw but Ake's filly (Kountry Plunge) is so much better than the others. She's not only the best in New York, but I think she may be the best in the country," said Gregory of the Chapter Seven-sired Kountry Plunge, a $200,000 purchase at the Lexington Selected Sale last fall that is the second foal from the 1:49 4/5 winning Plunge Blue Chip.

Kountry Plunge has won all four of her starts this year, including a 1:55 2/5 breeze over the half-mile track at Saratoga on August 18. More recently, Kountry Plunge was an open-lengths winner in a single Sire Stakes division at Vernon Downs on September 4, padding her first-year bankroll to $127K.

On the pacing side, Gregory has the right horse in the wrong spot for the sophomore filly pacing final (race nine), as Surreal Spirit landed post seven and will need some racing luck.

"It's tough from out there no matter how good you are," said Gregory bluntly about the draw.

Though Surreal Spirit exhibited 25-second first quarter speed in a New York Sire Stakes event at Vernon this August, Gregory recognized that came over a long straight path to the first turn.

"She's a big strong filly that has been racing well all season," said Gregory of Surreal Spirit, who was just a $13,500 yearling purchase at Goshen in 2024 and has now earned $222K during two seasons racing primarily on the New York Sire Stakes circuit. On the positive side for Gregory is that Surreal Spirit did in fact win at Yonkers in a leg of the Sire Stakes on August 6. On the board in nine of her 10 starts this year, Surreal Spirit is one of two fillies with the identical pedigree that are major contenders on Saturday.

"Her sister's quite a nice filly too," said Gregory of Cowboy Candy, the 2-1 favorite in the Sire Stakes final for 2-year-old pacing fillies. Like her older sister, Cowboy Candy was unlucky in the draw, landing post eight in Saturday's fifth race.

In addition to the three he's racing on Saturday, Gregory is looking forward to racing a Muscle Hill-sired freshman filly in the coming months at Plainridge.

"Nanny's Ce Ce is a filly I won with at Vernon a few weeks back," said Gregory. "I'm pointing her towards the Massachusetts Sire Stakes races."

Gregory had been tinkering with Nanny's Ce Ce's equipment in qualifiers, and the homebred has made significant progress over the last month. Her dam Bomb Hugger was a New York Sire Stakes finalist as a 2- and 3-year-old in 2021-22.