Twelve times a year, for 21 years and counting, West Point Thoroughbreds has received a training bill from Dallas Stewart. It is an owner-trainer relationship that began with a chance encounter but turned into a racing rarity in extending beyond 10 years, much less a couple decades.
Along the way, Stewart has defied the odds in his now trademark fashion in major races with West Point runners, finishing second in the 2008 Preakness with Macho Again and second in the 2014 Kentucky Derby with Commanding Curve, and he has gone on to win a slew of races with horses carrying the stable’s black and gold silks.
West Point has grown into the largest racing partnership in the world and now has horses scattered across the country with more than a dozen trainers, but Stewart has been the mainstay, dating back to his decision to go out on his own in late 1997 after a dozen years working for the legendary D. Wayne Lukas.
Stewart crossed paths with West Point founder and CEO Terry Finley at just the right time for both of them.
“I was in Saratoga, and we were just trying to hit our stride, and since New Jersey didn’t and still doesn’t have a year-round circuit, I felt a strong urge to come to New York and do a little in Kentucky,” Finley said. “I was sitting outside the racing secretary’s office at Saratoga near the end of the meet and Dallas Stewart walks out and says something to Buzz Chace, who was one of my mentors. He said, ‘Hey Buzz, I just told Wayne I’m leaving and I am looking for clients. I would appreciate if you could help me.’ Buzz introduced me to Dallas right there. I had certainly seen him around and knew about him from his time with Wayne and that he had galloped Winning Colors. But that was the introduction and we started sending him horses.“
Stewart picked right up with West Point’s Copelan Too, who had been previously been based in New Jersey, and finished second in the Grade 2 Kentucky Cup Sprint in September 1998 in his second start with the new barn.
Copelan Too was Stewart’s first West Point runner and Finley believes that not a day has gone by since then without at least one WPT horse on Stewart’s roster.
“He is not a pleaser, and we don’t need trainers that are pleasers,” Finley said of the keys to the long working relationship. “He bought into our program very early. He said, ‘Listen, I’ll train the horses, I can help you sell whenever I can, but that’s what I want to do, I want to train the horses.’ We have had trainers in the past who want to train the horses and train our Partners, and that’s not a model that works. They have to train as much as they can in a vacuum.
“He doesn’t train to not lose, he trains to win. I think that’s the difference between him and a lot of trainers. He has earned a lot of free rein over the years and has very supportive owners. He has our confidence. You want trainers to be building their masterpiece and when someone is more concerned about making a mistake or looking bad then about developing their masterpiece, that’s when you have problems and that’s when you are not as good as you can be.“
Finley relied on Stewart’s gut instinct as well as an open mind to outside opinion when the decision was made to run Macho Again in the 2008 Preakness after a victory in Churchill’s Derby Trial Stakes.
Finley recalled: “We had just started using the Ragozin Sheets and right after we won the Derby Trial, our Ragozin consultant said to me ‘When are going to ship that horse to Baltimore for the Preakness?’ I hadn’t really thought about it, we were looking more for a race like the Ohio Derby, but I brought it up to Dallas and he started mulling it over. He is very much a gut-feel guy. He felt good about it, and we were all in. That worked out great.“
A few months later, Finley was inclined to take on Big Brown again in Monmouth’s Grade 1 Haskell, but Stewart lobbied instead for the Grade 2 Jim Dandy Stakes, feeling the late-running horse would be better-suited to the track at Saratoga. Finley went with Stewart’s take and Macho Again delivered a Jim Dandy victory at 8-to-1 odds.
“That horse is a good example, I think we work well together, bouncing things off each other,” Stewart said of Macho Again, who went on to win the Grade 1 Stephen Foster Handicap. “What has made it last so long? Well I hope to God he thinks I can win a big race for him and his clients and continue developing good horses. Honesty has always been the best policy for both of us, and we have a lot of great memories together, from right off the bat. That goes a long way.“
When Commanding Curve came flying to finish second behind California Chrome in the Kentucky Derby, he flipped the script just a week after turning in a disappointing final workout.
“Dallas was one of the only people in our camp that wasn’t concerned about Commanding Curve after that workout,” Finley said. “One of the things Dallas has taught me is that they are not machines. They are not going to go out there and work picture perfect every time. You can’t get overly excited when they work great and you can’t get overly concerned when they don’t work great. There are all kinds of reasons why that happens. You know, as soon as a horse gets beat or has a subpar work, the impulse is think ‘Uh oh, the wheels are falling off or they have fallen off.’ There is so much that goes into having a horse work well. With Commanding Curve, it was a poor work the Saturday before the Derby. He was never an exceptional work horse, but this was subpar even for him. If there was something that was biting him, it was going to show, and if there wasn’t, Dallas’s thought was to just put it behind us, and rightfully so. We agreed not to focus on it. Internally, we stopped even talking about it. It was done, we had no control, and Dallas has that ability to consistently be looking ahead. He acknowledges the past but he keeps looking forward.“
West Point Executive Vice President Jeff Lifson rubs shoulders with Stewart on a day-to-day basis at Churchill Downs, where Stewart won three races from five WPT starters during the just-concluded spring/summer meet. Over 15 years working together, Stewart and Lifson have developed a strong bond.
“Dallas is a remarkable person to work with,” Lifson said. “He is a ton of fun to be around and at the same time he is one of the most serious and single-minded, focused trainers I have ever been around. I don’t know how he pulls it off, but he does. He is also the guy in the shedrow you know when to step back away from because he is so micro-focused on the horses. He is an observer, and I think training horses is a lot about observation. Some guys do it because they have to. He does it because he loves to. He loves training horses.
“The other thing that shines through with Dallas is just his passion for life in general. He is nuts about his kids. He calls them every day and ends up the conversation with ‘I love you.’ His passions for life include food. You are driving to the other side of the racetrack to watch horses train and he is telling you how he cooked his fish for dinner last night, where he picked it up. He is passionate about the New Orleans Saints. He is all about family, horses, football, friendship–you’ll never have a better friend than Dallas–and all that makes him such a joy to be around.“
An infectious and affable personality, combined with results on the track–that chance encounter at Saratoga back in 1997 has been a godsend for Finley, West Point and its clientele over the last 21 years.
“It’s fun for me, seeing so many people enjoy racing through West Point,” Stewart said. “I love seeing those silks coming into the winner’s circle, I can tell you that.“
