Family Matters – The Hennessey brothers credit their relationship and pedigree for their success
story by Ken Weingartner
A variety of words can describe Dan and Wally Hennessey: drivers, trainers, record breakers, history makers, hall of famers. But those words create simply a sketch of the brothers’ lives in harness racing. For the complete picture, one additional word above all others is vital.
For nearly 40 years, Wally and Dan have operated a racing stable together; first in the Canadian Maritimes and, since the mid-1980s, in south Florida for the fall through spring, and Saratoga, N.Y., in the summer. Wally has won numerous driving titles at Pompano Park and Saratoga Harness during his career while Dan has captured multiple training titles at Pompano. In 2017, Dan and Wally became the first brothers to claim top honors as trainer and driver at Pompano for the same meet.
Wally, best known for his six-year association with the legendary female trotter Moni Maker, is a member of the U.S. Harness Racing Hall of Fame, Canadian Horse Racing Hall of Fame, and halls of fame in Florida, New York and on Canada’s Prince Edward Island. He has won nearly 10,000 races, ranking No. 18 in history, and posted a driver rating of at least .300 in 28 of the past 29 years. His lone miss came in 2001 when he finished at .295.
Dan, who lost sight in his left eye in 2002 because of a tumor and since 2014 has suffered vision problems in his right eye because of a detached retina, has trained more than 1,000 winners and produced a 20-percent victory rate over the past 28 years. He is a member of the Florida Harness Racing Hall of Fame.
“We’ve had each other’s back, well, forever,” Wally said about Dan, and it is far from hyperbole because the brothers have been side-by-side, well, forever.
Dan and Wally grew up in Charlottetown on Prince Edward Island, the sons of Shirley and Joe Hennessey. Dan was the fifth of the couple’s nine children, born in 1954, and Walter—Wally’s given name; he was named after Joe’s father—followed two years later.
Joe Hennessey got started with horses at an early age, thanks to his dad, known as Wal, and grandfather, Mike. The family used horses to deliver bread for a bakery, but also was involved in harness racing. Joe learned from his father and other PEI horsemen of the era and opened his own public stable in 1956, the same year his father died.
Of the Hennesseys’ nine children, five were boys and all could be found working at the family’s stable while growing up. Four of them—Dan, Wally, Jody and Gordie—continued in the sport. The remaining brother, John, became an attorney.
“We were brought right into harness racing from the time we were hatched,” Wally said. “It was work, but it wasn’t work. It was something we had to do, help at the barn to make the ends meet. From my own perspective, I never thought about anything else.
“When I watched my father as a young boy, the adrenaline and the highs that you get when you take care of the horses and they do well just made you feel like you accomplished something.
“Even though you weren’t in the bike or maybe didn’t own the horse, you felt every bit as proud and as happy for everybody.”
The lessons learned at the barn and from Joe proved priceless.
“He was a good man. He was a good role model; I can’t say enough about how much we learned from him,” Dan said. “He taught us how to work, first and foremost. And honesty—he was the most honest man under the sun. The rest just falls into place after that. We just picked up everything from him as we went along.”
While their father had a profound influence on their lives, the family was impacted equally by mom, Shirley.
“Our mom was superwoman. She raised nine kids, none of us in jail,” Dan said, adding a laugh.
“She fed everyone at the track because we were always hauling somebody home at dinner time, friends or whatever,” he continued. “She fed all of us, plus them, and she loved it. The more the merrier. There was always enough.”
Joe and Shirley were a match made in heaven, according to Wally.
“My dad had a one-track mind and that was horses, whereas my mother was more diversified,” he said. “She could bring up any subject and she was very witty and funny. They were two different people altogether, but a great match.
“Our mother was our support system. She would never bring it up, but if you did need someone to give you a pat on the back, she was the first one there. She did it not only for our family, but for friends and complete strangers. She was just a unique individual. She was a very kind, caring woman.”
How much of the Hennesseys’ success can be attributed to their family life?
“All of it,” Wally said. “We didn’t realize, growing up, how great an upbringing we were provided, all nine of us. Our whole crew, we were very lucky. We knew it, but we didn’t know it. It was just one of those deals; you go home every day and you take it for granted.”
Wally never wanted to do anything but work with horses. Except for a six-hour stint working on a boat, a job lined up in Saint John, New Brunswick, by his father, he never did. Of course, whether that stint counted as work is open to debate.
“I think he slept on the boat for six hours and when he got up he left,” Dan said.
“I got off the boat and went over to the racetrack,” Wally said. “In two or three years I was the leading driver. It’s kind of how life goes. I never thought about my future. I never thought where it would take me. Everything just fell into place. It was something I thought I was going to do my whole life and I was lucky enough that it ended up that way.”
Not that success came quickly. While Wally is remembered for a succession of record-setting years for wins and purses in the Maritimes in the early 1980s, he struggled at the outset of his career.
“My biggest thing was, I think, that I held my father in such high regard when it came to everything, but especially what we did in harness racing,” he said. “When I first started out, I wasn’t doing any good. I was feeling bad enough myself. I thought I was going to conquer the world when I got my license, but I was more upset that I was letting my father down. He never said that to me, but I felt like I wasn’t living up to his expectations or mine.
“That was kind of a driving force to keep at it because I knew I could do it. I knew I wasn’t this bad. There was no way I could be this bad.”
Wally and Dan soon had a powerful stable in Saint John. During that time, Wally began vacationing during the winters in south Florida and imagining what it would be like to compete at Pompano Park. In 1986, the Hennesseys and a group of their racehorse owners decided to give it a go.
“I was doing as good as I could do at home; I didn’t think I could do much better,” Wally said. “I had owners that were willing to invest in me and they wanted to go to Florida as well. We took the stock we thought could do well in Florida and southward bound we went.”
Again, success was not immediate.
“We found out not too long after we got there that we didn’t have the power to be at Pompano,” Wally said. “Plain and simple. It didn’t matter what we tried to do, it wasn’t going to work because the horses just weren’t strong enough.”
That might have been the end of the Hennesseys’ story in the U.S. if not for Warren DeSantis, who had been the race secretary at Pompano Park and was hired to be general manager at Saratoga. Wally and Dan were prepared to return to Canada, but DeSantis persuaded the brothers to stop at Saratoga on their way home.
“He knew Wally had talent, so he wanted him there,” Dan said. “We weren’t going to go because we didn’t think we had the stock, but Warren said to stop and stay for a month and if it didn’t work out, then go home.
“Our horses fit like a glove there and the rest is history.”
Thanks to their success in New York, the Hennesseys decided to give Pompano another try. They created a winning stable there, and their work did not go unnoticed.
“The biggest thing that happened to Wally and Dan Hennessey in our careers is that when [Hall of Fame horseman] Stanley Dancer retired, he had a couple of horses left and he came over and asked us to train them,” Wally said. “That was the biggest endorsement we ever got in our careers. That was one of the greatest of all time coming in and wanting us to train. That was huge. I guess our choice to go to Pompano was OK.”
On the track, Wally became a force on the New York Sire Stakes circuit and began seeing an increased number of drives on the Grand Circuit. In 1992, he posted his first major stakes win when he guided America’s Pastime to victory in the Woodrow Wilson for trainer Joe Holloway. His career reached a new level in 1996 when he won the Hambletonian Oaks with Moni Maker and his first Breeders Crown with Running Sea.
Moni Maker, trained by Bill Andrews at ages 2 and 3 before joining the Jimmy Takter stable, was Horse of the Year in 1998 and 1999 and Trotter of the Year in 1998, 1999 and 2000. In addition to the Hambletonian Oaks, Wally and the mare posted many memorable wins together, including the Elitlopp, Breeders Crown Open Trot and three editions of the Nat Ray. Moni Maker retired in 2000 with a then-record $5.58 million in purses.
“There is nothing better than seeing your brother at the head of the stretch going forward in a big race,” Dan said. “There is no better feeling in the world. You can’t buy it.
“Our family is very proud of Wally. We all have nothing but the greatest respect and admiration for one another and we each hope the others do well. That goes back to our parents. We cheer for each other.”
Others were cheering, too. Mark MacDonald, a two-time winner of Canada’s Driver of the Year Award in the mid-2000s and the winner of numerous Grand Circuit stakes, grew up in Charlottetown not far from the Hennessey family and was energized by Wally’s exploits.
“Wally was a hometown hero for sure,” MacDonald said. “He grew up the same way I did, cleaning stalls in Charlottetown. When I was a kid, that’s where I was. You look at Wally and he was driving Moni Maker and racing in the Hambletonian, all the Meadowlands’ big races, and you think that if he can do it maybe I can too. It’s a long shot, obviously, but you never know.
“Like anything in life, you have to set a goal.”
MacDonald continues to look up to the Hennesseys, while enjoying their friendship.
“They’re great guys,” he said. “They’re just fun. They’re Islanders, through and through. I still look up to Wally. He’s the ultimate professional, in my opinion. Dan is a super-nice guy and a hard worker. They have a smaller barn now, but they run a Grand Circuit-style barn. It’s first class.”
Dan, who did some driving during his career prior to his eyesight issues, is happy to direct his attention on the training side of the business.
“I could get on the bike, knew what to do and when to do it, but I just couldn’t get it done,” he said. “Whatever move I was making, I’d be a half a second or a second too late, or too early. I enjoyed my end of it much, much better—doing the jogging and training and running the barn. I enjoyed that part much more. It’s the excitement of the whole thing. Getting a horse to go forward that wasn’t going forward before you got him, things like that.”
The stable has been a blessing for Dan as he battles his vision issues. He recently had a sixth surgery on his right eye to maintain his limited sight.
“It’s quite a grind,” he said. “It’s quite a change of life for a person when you can’t jump in your car and go someplace because I can’t really see good enough to drive. And you can’t sit behind a horse anymore. But thank God, I’ve got the horses. I can still get there and work around the barn. I can still do my thing in there. If I didn’t have that, I’d be out of my mind. That’s what keeps me going. It’s great to get up every day and do what you love.
“It’s been great for both of us, I think,” he added, referring to Wally. “When one of us is down and out, the other one is there. We’ve each got a shoulder to lean on, if need be. It’s been a good thing. He’s my best friend, and vice versa, besides working together. We’ve always got along great. It’s been a great relationship.”
“We’ve been a great team,” he said. “Dan is the glue. We’re not excuse-makers, either one of us, and we have the same drive for success.
“We’ve been together so long, you don’t even realize it. It’s just part of life. We’ve been blessed. At our ages, to still be able to do this and be able to compete, it speaks volumes. Maybe that’s why we’re still able to do it. We’ve been able to rely on each other. We’ve seen a lot of people come and go, for sure. We’re able to complement one another. It’s been great and I hope it keeps going for a little while longer.”
Ken Weingartner is the USTA Media Relations Manager. To comment on this story, email us at email@example.com.