After 56,000 miles around the track and half a century feeling the rush of the race, Wally Hennessey now finds himself staring down the one finish line he never wanted to see. The Pride of PEI. The King. The Mayor. The Hall of Famer. The Legend - each title marks a chapter in the storied career of Hennessey; a career defined as much by resilience and success as by the horses who carried him. Fifty-one years ago, Hennessey climbed into the bike for the first time. The son of prominent Maritimes horseman Joe Hennessey held more than just a set of lines, but the full weight of his family's legacy in the sport of racing. He was raised with the old school values of life and racing. Early mornings were spent learning from the ground up. Before he ever sat between the shafts, he was mucking stalls, sweeping aisles, and learning the small details that define the best horsemen. "I come from a harness racing family," Hennessey said. "My grandfather raced and owned horses, my father, my brothers, and then myself. My earliest memories are going to the barn with my dad. I was really young, maybe 6 or 7 years old, grooming the horses and cleaning the leather harnesses. My dad was such a professional and wanted everything done in a first-class manner." Joe Hennessey was a well-regarded horseman. Hennessey describes him as a man of few words, someone you wouldn't learn from by communication, but rather watching him in action. Whether it was the way his father acted and interacted with horses, grooms, owners, competitors or people off the street, Hennessey aimed to pattern his character off of his father's - one that was professional and held in high-esteem. Eventually, Wally Hennessey emerged from the shadows of the shedrow and found himself behind his first horse. Even then he knew that it is where he belonged. "My father was a tough teacher. He wasn't quick to allow you to do things right away; even to put a bandage on a horse or to jog a horse. My initial jogs were sitting on the seat with someone else, only about 6 or 7 years old. From the time I can remember, I was sitting in a jog cart or grooming horses. I started jogging at a very young age," said Hennessey. The smell of the horses, the aroma of the stable and watching his father compete on the track were all factors that contributed to Hennessey's early passion for the game. He knew that competing as a driver was where he wanted to be, but he wasn't sure if was going to be able to do it. All he knew was that he was going to make it his mission to succeed. The beginning of his career was anything but smooth, with his early drives punctuated by the jarring feel of impacting the ground. Several times Hennessey was involved in accidents, ending up staring at the sky and covered in dirt. "I had been doing this my whole life. You couldn't get licensed in Atlantic Canada at that time until you turned 18 years old. By the time I turned 18 years old, I had all the experience. Rubbing horses, jogging, training in sets, all of the above. I believed from watching it that it couldn't be that hard. I had tons of experience before I ever even went behind the gate," Hennessey said. "When I first started to try and get drives it's not like today's generation. With the older generations, my father's generation and the ones above and below him, it was very hard to get any type of an opportunity to drive. Even though my father had a big stable and my older brothers were driving, I really didn't get the opportunity right away. "When I did get the opportunity, I would say in my first 10 drives I was in an accident maybe three or four times; on the ground. Each and every time, it was more my fault than anyone else's. Having started like that, you would wonder to yourself why would you keep going? To get all busted up that early. Fortunately, I didn't get hurt bad any time that I happened to get in those accidents. I think what made me keep digging in and keep going was number one, that I thought I couldn't be this bad and number two, that I believed I was embarrassing my family because our family had such a great name in the industry." While Hennessey didn't believe he was the center of attention on the Island, he said he wouldn't be surprised if there was some talk about 'that kid being down again.' "I had to dust myself off again and I thought, 'who would ever put me down to drive?' People were probably afraid that if they put me down, I would get their horse in an accident. I didn't get many opportunities," said Hennessey. That was a turning point in his career as he packed up and left his home in Prince Edward Island to go to New Brunswick for a new chance to see if he could become a driver. "Looking back, it was the greatest thing that could happen, because it taught me so much in my early years, and to this day when I go out on the track I am so focused. I don't think I was focused that much when I first started, and I believe that's why I was getting in so much trouble," admitted the 69-year-old. Though he had a rough start to his illustrious career, Hennessey turned the tide to become the Pride of PEI. His first win came in 1975. The feeling of that victory is one that Hennessey has been chasing his entire career. "The first for anything is great, but as bad as I was, as horrible as I was doing, I never, ever thought I was going to win a race," Hennessey said. "I thought it was the end of the world. The feeling that I got that particular race, winning that race, is why I am still doing it today and why I was doing it then. I've never had that feeling again, as many races as I had won, nice races and good horses that I had driven. It was surreal. It was like you were in somebody else's body. Just that feeling that night, I'm still looking for that." After that first win, there was a shift in Hennessey's career that led to the coinage of the Pride of PEI. He set the standard for most wins and most money earned in a season by a Maritimer before going on to rewrite the record books across North America. Returning to Prince Edward Island to drive during Old Home Week throughout his career, Hennessey secured a pair of Gold Cup and Saucer victories to solidify his stature as a fixture on the Island and honor his family's namesake. Along with being the Pride of PEI came being the King. First, it was the King of the New York Sire Stakes. In 1992 he won seven New York Sire Stakes events at Buffalo Raceway. His domination in the stakes gave him his second title and a new chapter in his book, but it was his name as King of the Pomp that proved his most career-defining chapter. During the late 1980s, Hennessey relocated to the United States, and to this day he has a permanent home in Coconut Creek, Florida, with his wife Barb and daughter Kristy. For 40 years, Hennessey was a staple in the south Florida harness racing community at the "Winter Capital of Harness Racing," Pompano Park. For 40 years he remained at the top of the driving standings at Pompano, earning several driving titles and awards for his success. He was the King of Pompano Park, later shortened to The Pomp, in credit to announcer Gabe Prewitt. ► Sign up for our FREE DRF Harness Digest Newsletter During the final year of racing ever at Pompano Park, Hennessey was coined the Mayor of the track for his decades of commitment and success on that five-eighths mile oval. On the final night of racing, his first notable win came with Panocchio, a track record-holder at Pompano. To celebrate the win and to pay tribute to the track, Hennessey pulled up in the far turn and climbed on top of the seat. Balancing atop the bike with the lines in his hands, Hennessey paraded to the winner's circle in homage to the Herve Filion celebration with one foot in the seat and one foot on the crossbar. Later that night, Hennessey won the final race ever contested over the white sand and stonedust with Beach Forecast. Reflecting on his accomplishments, those wins at Pompano Park on that final night and even achieving his 12,000th win earlier this summer at the Saratoga Harness Track, Hennessey said that all of the emotions come rushing back. "I get emotional a lot more than I show. The reason I keep it inside; I don't believe you should show your hand. I don't want anyone to see a weakness in me," Hennessey said. "The 12,000 wins, I knew was going to be my last milestone; winning the last race at Pompano Park, I knew it was going to be the last win at Pompano Park; and winning with Panocchio that night, I knew it was Panocchio's finest moment, being a track record-holder at a racetrack that so many great horses have gone over and he being the fastest and one of the best that ever went over Pompano Park; just for me to have that opportunity to drive him and win. There's been hundreds of emotional moments, wins or not wins." Hennessey has had tens of thousands of trips to the track with thousands of different horses for different trainers in every race from the bottom class to the highest Grand Circuit event. His success has earned him his Hall of Famer title as he has entered six different Hall of Fames, including the United States Harness Racing Hall of Fame, the Canadian Harness Racing Hall of Fame, the PEI Sports Hall of Fame, the Florida Harness Racing Hall of Fame, the Florida Sports Hall of Fame, and the Saratoga Harness Racing Hall of Fame. All of that together - the Pride of PEI, the King, the Mayor, and the Hall of Famer - linked with his most notable achievements on the racetrack have led Hennessey to his status as a Legend. He has won so many different races, from the Hambletonian Oaks to the Breeders Crown to the Elitlopp and more. His wins span across North America and all the way overseas to places such as Sweden. Most notably in terms of horses he has steered are Cambest and Moni Maker. "Nothing else I have ever done in my career or will do in my career will compare to my years being associated with not only Moni Maker, but the people associated with her as well. Nothing will ever compare to that because not too many people ever get that opportunity to be associated with a horse of that caliber. People that weren't even born when she raced know who she is. She is an icon of the sport," Hennessey said. Altogether, his résumé extends far beyond many that have ever held a set of lines, and he continues to win at a high level at the Saratoga Harness Track. But now as his time at the Saratoga Springs, New York, half-mile closes for another year, Hennessey faces the decision of whether or not to hang up the lines for good. The legend feels that he has been very fortunate throughout his career, and though he has no interest in ending his driving career, he wants to end his career on his own terms rather than be forced out due to other circumstances, such as an injury on the track. In 2023 Hennessey was involved in a near career-ending accident at Tioga Downs when he hit the track just right and injured his back. Fortunately, there were no long-term consequences, and as a typical horseman would do, Hennessey was quickly back in the bike. "That's one thing about racing - accidents do happen. It's not if they'll happen, it's when. That one at Tioga wasn't one of the nicer ones that I've been in and like I said, I've been in accidents starting in 1974. That one could have been career-ending, but fortunately somebody was looking down on me, and I was able to recoup from that. Having said that, I never think about that when I'm racing or going out to race. If I had that mindset going out, I definitely wouldn't be able to compete," said Hennessey. "It's a big part of why I'm thinking of going out now because I think I've pushed the envelope far enough that, what am I waiting for? Am I waiting for something to end my career before I can end it myself? It's okay to walk away without having to walk away because of an injury or because people are looking out at you saying why is that old man out there? I believe I've pushed it far enough." With all of the milestones and triumphs and everything in between, Hennessey believes the thrill of the race is the thing that keeps him going. The wins and the rush that come with them are going to be hard to let go of, he said. "I'll miss the actual adrenaline, the competing and the adrenaline that comes with it," Hennessey said. "I work hard to keep at the level that I'm at. I don't take it for granted. I like to study the program, I like to know the horses that I'm against, I like to know the people that I'm racing against, and I like to know the starter. I'm a student of the game and always have been. To know whether the track is playing speed-favoring or if you're able to come from off-the-pace. Before I go out on the track, I know exactly who I'm in against, what they can do and can't do and what they've done. "To sit in the seat and have the same talent as somebody else, if you're more prepared than that guy and you've studied more and you're more zoned in, you have an edge. It might not be a big edge, but it's an edge," Hennessey added. Regardless of whether or not Hennessey hangs up the lines, and though he is not sure if he will continue as a trainer or what his next chapter will entail, he is sure that the horses will always be in his life. "I know the time is now. I'm struggling with life without the competition, the adrenaline, the horses, the camaraderie, my identity. It's who I am. When you give this up, it will all go away. The thought of not competing and not winning a race. The feeling I get today is the same feeling I got when I first started. It's irreplaceable. It's like hitting a grand slam, scoring a touchdown, getting a slam dunk. No matter what, though, even if I stop driving, the horses will always be a part of my life," said Hennessey. Flashing back to that kid that was just starting out, carrying the weight of a legacy on his shoulders and fearing being a disappointment to that legacy as he hit the track far too many times, to now being on top of the world 51 years later with his own legacy at his heels, Hennessey has carved his name into the fabric of the sport. "Who would ever think a kid from Charlottetown like me would end up on the biggest stage all over the world," said Hennessey. "I know how fortunate I've been in that way and how fortunate I've been to last this long. I've been fortunate my whole life that I've been able to stay at a competitive level and make a good living at it. I just believe that I don't want my career to end because of some other reason other than that I'm ending it, as far as driving. "It's not an easy decision. It's hard to walk away from something you've done your whole life," Hennessey concluded.