The heaviest ever staked a horse for Jeff Gregory

Before driver Jeff Gregory enjoyed memorable victories with horses such as Bubba Dunn, Jalopy, Chapter Seven, and You Ato Dream, there was Rambling Roxie.

A female pacer trained by Gregory’s father, Gary, she gave Gregory his first win.

Twice.

Owned by a family friend, Rambling Roxie carried Gregory to victory in his first matinee drive at the age of 14 and several years later to his first pari-mutuel triumph, also in his first try, in 1984.

“It was kind of crazy, but it happened,” Gregory said of the wins with Rambling Roxie. “She was just an average pacing mare, but she tried, and she was easy to drive.

“When I got my license, we had a bunch of horses, and my father let me drive one horse. He said you’re comfortable with her, drive her. Then after a while I started driving two, then three, then four. But I started off with one and she was the one.

“He wanted me to learn on our horses that I was comfortable with. It benefited me. I was so comfortable with our horses it gave me a little more confidence driving in the race. I knew their capabilities.”

Gregory grew up in northwest New York, not far from Rochester. He jogged horses while sitting in his father’s lap by the time he was 5 or 6 and never thought of doing anything other than working with the horses.

“We had a nice stable of 15 to 20 horses most of the time,” Gregory said. “We had a lot of horses to learn on. I was a very lucky kid. My mother (Sue) helped in the barn and my father trained horses for 50 years before he retired a few years ago.

“I was at the barn every day, all summer, every Saturday, every Sunday. I didn’t play any sports in school because I didn’t want to go to practice on Saturday. And I didn’t want to go to the games on Friday or Saturday night because I wanted to go to the paddock. I had to go to the track.”

In 2012, Gregory’s dad was inducted into the Upstate New York Harness Racing Hall of Fame.

“I was brought along slowly by my father,” Gregory said. “He was by far the biggest factor in my career, my only teacher. I worked for him until I was about 20 and then he pushed me off on my own.

“He was a very well-respected horseman, which helped me with my clients. They knew I was taught the right way. But other than my dad, I’ve been self-employed my whole life. I never worked for another trainer. He just kept pushing me in the right direction.”

Gregory’s favorite horse while working with his dad was a trotter named Coaltown Smoke.

“He’d been a problem horse for a bunch of other trainers, but we got along good with him,” Gregory said. “He was a very finicky horse, very temperamental, but he ended up being an open trotter for a long time. I loved the horse.”

Gregory was primarily a catch driver through the early years of his career. More recently, he returned to training a stable as well as driving.

“Knock on wood, it’s been a successful career,” said the 54-year-old Gregory, who has won 6,920 races as a driver.

In 2002, Gregory won the Yonkers Trot with Bubba Dunn for trainer Jeff Smith. Three years later, he captured the Hambletonian Oaks with Jalopy for trainer Jonas Czernyson, besting favorite Blur by a nose.

“Winning the Yonkers Trot was a big thrill, my first major race,” Gregory said. “And winning the Hambletonian, whether it be the Oaks or the boys, it was all you ever think of as a kid who loves trotters. That was big.”

In 2011, Gregory headed to the Breeders Crown finals at Ontario’s Woodbine Racetrack to drive Joe Holloway-trained trotter For A Dancer. He finished third with the filly, but also picked up several other drives on the card after a snowstorm prevented a group of drivers from making it to Canada.

One of the drives was behind Linda Toscano-trained trotter Chapter Seven, who Gregory guided to victory. He also had a second-place finish with pacer Handsoffmycookie for trainer Scott DiDomenico.

“I can probably thank Joe for that because he told me about three days before the race that the weather was going to be bad and not to mess around,” Gregory said. “I ended up going on an early plane and I got there on time.

“It was a huge night.”

This year, Gregory is hoping to enjoy some more huge nights (and days) with 3-year-old filly trotter You Ato Dream. She is preparing for this week’s Hambletonian Oaks eliminations, coming off a career-best 1:52.2 win in a division of the Del Miller Memorial on July 17 at The Meadowlands.

Gregory trains the filly, which he co-owns with Bill Richardson, George Romanoff, and Martin Garey. For her career, You Ato Dream has won five of 17 races and $384,498. She has hit the board a total of 13 times.

Last year, You Ato Dream had four second-place finishes by a neck or less, including in the Pennsylvania Sire Stakes final and two Grand Circuit starts at Lexington’s Red Mile.

“She needed a bigger nose,” Gregory said with a laugh. “But it always felt like she was trying.”

This season, You Ato Dream opened her campaign by going off stride in a loss at The Downs at Mohegan Sun Pocono. Since then, she has won four of six starts.

“Our first start at Pocono was a disaster,” Gregory said. “We made a couple of equipment changes in her mouth and since then she’s been really easy to drive. Now that I can sit in a little bit with her, she’s able to beat some better horses. It’s really helped us.”

Gregory is looking forward to the remainder of the Grand Circuit season with his filly, particularly the upcoming Hambletonian Oaks.

“We’re looking forward to it,” Gregory said. “The chances of winning are not great for everyone, but it’s a chance for us to dream. This is probably the heaviest I’ve ever staked a horse. Knock on wood, so far, she’s shown she can go with the better fillies anyway.

“She’s been a pleasure. I’ve got a core group of owners that are older guys that have been around forever and seen it all, the ups and downs, and this is the best horse they’ve had. They’re really enjoying it. Over the years, we’ve bought a lot of horses, and (ones like her) don’t come by that often. We know how lucky we are to have her.”