Rewind: 2005 Gold Cup & Saucer

"Anybody's who's ever went there has always talked about it, and that part of the prestige that goes with the Gold Cup & Saucer is that it's a bucket-list race on everybody's calendar. One time in their life, they'd like to be there and of course have a horse in it. And then to win it, it's just the icing on the cake."

Ten years ago this week, Hall of Famer Wally Hennessey made Maritime history by guiding Driven To Win to victory in the 2005 Gold Cup & Saucer. The son of Jennas Beach Boy - Shes The Greatest was a product of world champion bloodlines very familiar to trainer and co-owner Joe Holloway, who campaigned both Jennas Beach Boy and the full sister to Shes The Greatest, Shes A Great Lady. Racing in the free-for-all ranks in the U.S., and owned by strictly stateside owners, the choice to ship to Charlottetown might not have seemed all that obvious. But the horse had Island connections within the Holloway barn, and that's where Hennessey points all the credit for this plan coming to fruition.

"The horse was with Joe Holloway in New Jersey and (assistant trainer) Scott Bell contacted me and asked me if I was interested in going home to race in it for the elimination and the final," Hennessey told Trot Insider. "I accepted, believing when I accepted that I had a really good chance of winning.

"I knew he was a good horse and knew all about him, and thought I had a more than above-average chance of winning the race. Once I made my commitment, no matter he finished in his elim I was going to hang around for the final...but as it worked out, both times he drew good."

Hennessey and Driven To Win were comfortable winners in Trial #1, raced on Saturday, August 13, 2005. The duo connected for a 1:54.4 score.

"I don't know whether it made a difference or not but in the elimination race, the way the race went he finished so strong and without me even asking him," Hennessey continued. "He was fresh going into the final and that makes a big difference."

Two days later, Sand Olls Dexter made a statement of his own. The two-time defending Gold Cup & Saucer champion and driver Mark MacDonald sped to a track record 1:52.4 score in Trial #2. That time erased the 1:53.1 record of 1999 Gold Cup & Saucer champ Native Born. The showdown was set for the final with Sand Olls Dexter drawing post five. Driven To Win, post one.

Hennessey was confident in his horse, despite facing the defending champion who was two full seconds faster in his Gold Cup & Saucer trial.

"[Sand Olls Dexter] had won the last couple of years and raced so huge; he raced good in his elimination also. You have to understand, the people who there the two years prior, that's what they were basing their handicapping on. And with Driven To Win, they'd seen that he'd won...believe me, post position did play a part. Going into that night, Driven To Win...I think he was the best horse."

The best horse can lose a race, however. Hennessey was quick to credit Bell for ensuring the horse was in prime form heading into the 2005 Final.

"He had a good week after his elimination. Scotty did a really good job keeping him up and being prepared and ready.

"He was sneaky fast, he didn't really look like he was...and he was a handy horse, and you have to have that on a half. And he was a horse that you didn't have to guide around the turns, he could pace the turns as well as he paced the straightaways. That's huge on a half mile. And he was a well built, compact horse."

When the clock struck midnight on the Gold Cup & Saucer card and the wings of the gate folded, Hennessey's plan was clear.

"On the half-mile track, [it shows] how important it is to draw on the inside...plans don't always work but my plan was to put him on the front end. The other horses left hard but we left just as hard."

Driven To Win's first fraction flashed up in :27.1, followed by a :27.4 second quarter and a third-quarter 'breather' of :28.3, pacing the fastest three-quarters -- 1:23.3 -- in Charlottetown Driving Park history. As the rest of the field felt that pace catching up to them, Hennessey and Driven To Win pulled away to a seven-plus length 1:51.2 track and Canadian record score.

"He won it handy. At that time, that was a pretty fast mile. The connections had him sharp and, listen, I was just a chauffeur. The horse was good, we drew good.

"To win it, you can't explain the feeling. Anybody who says they're not geared up that night, if they're a part of that race ...anybody for that whole day or the days leading up to it, if they say they're not geared up for it they don't have a pulse."

A Gold Cup & Saucer winner for the first time in 2001 with Scarlet And Gold, Hennessey considers both wins equally special and meaningful.

"Being from Prince Edward Island and winning it...it's a special feeling just to be involved and be a part of it for the whole week, and then to win it, it's something else.

"As far as comparing which one meant more, or which one thrilled me more...they're equal. Both times, it was the trainers -- that being Scott Bell and the time before, Billy Companion. Billy Companion raced against my father, his father raced against my father...and Billy thought it would be pretty cute if I'd come, him being the trainer and me being the driver all those years later and do some good."

As Charlottetown enters Old Home Week, Hennessey gushes with pride over how his hometown and its staple harness racing event have transcended local prominence to become internationally recognized.

"For Island people, not just the Gold Cup & Saucer but the whole week ... we're really proud of it, what it's become and how the people that run it, what they've done with it. They've taken the ball and ran with it, and made it such a big international deal now. It's known all over the world and it just started out as a small, little race for Maritime horses, double dash and best summary. And here we are, talking about it today and it's known all over the world. So the guys that took it to the next level they deserve a lot of credit. The track, the management and all the people responsible for how it happens."

That recognition was evident even with the 2005 event. While most owners surely try to make to Charlottetown for the Gold Cup & Saucer, Driven To Win's connections could have been excused for not being in attendance. After all, they did have a horse racing closer to home in a leg of trotting's Triple Crown. Strong Yankee was set to race in the Yonkers Trot -- held at Freehold Raceway due to construction -- and still, the connections chose Charlottetown. (Strong Yankee, for the record, won by five lengths in 1:56.1.)

"Everybody in North America knows about the Gold Cup & Saucer...it's not like when you talk about it, it's strange to them. They know exactly what you're talking about, " said Hennessey. "They chose to be in Charlottetown, and they had a really wonderful experience...as everybody does when they go there."

(Photos courtesy Gail MacDonald)