Winning a Stakes and Keeping Your Cool

Ninety North Racing Stable's Thieves Guild (above, warming up) won the Caress Stakes on Aug. 2 at Saratoga Race Course. (All photos courtesy of Kathryn Sharp)
It’s the dream. It’s an unrealistic, expensive, time-consuming, defeat-driven, jealousy-inducing dream, but for two kids in the racing business, it’s the only dream there is: winning stakes races.
It’s not the first stakes we’ve won. On a chilly, rainy day in October 2012, our $4,000 gelding Two Months Rent took us to Hawthorne Race Course and won us the Grade 3 Hawthorne Derby at 20-to-1. I count it among the best days of my life. Maybe they could have heard us screaming from the Drake Hotel in downtown Chicago if they’d bothered to turn down the Notre Dame football game playing at the time. I was thrilled, I was proud, I was in disbelief, but I didn’t know how good I had it. We had just won a graded stakes only a year into my journey in the racing business. It was so much fun. He was a horse we loved, and it made for a great story.
Turns out, great stories like Two Months Rent’s Hawthorne Derby win are hard to come by in horse racing. Three years later, we hadn’t won another stakes, graded or otherwise. We had plenty of chances; we ran good horses on big days, but that win was elusive. It wasn’t the only accomplishment that had eluded our East Coast-based stable of 12 horses. We had yet to win a race of any kind at the most prestigious race meet in the country: Saratoga Race Course.
We brought a knockout lineup of runners to the Spa in 2014, and we came close a number of times, but we couldn’t run our way into the winners’ circle. Justin and I watched as plenty of familiar names marched their way into that hallowed trackside oval: old pros in an impossible game.
“I want that win so badly I can taste it,” I frequently told Justin, friends and passersby. The complaint fell on sympathetic ears. They all know; they’re in the game, they want it, too.
As the meet started in 2015, we stared at our roster and like fools, we hoped. Could this be the year? When I arrived at Saratoga on Saturday morning, I walked the shedrow and looked each of our horses squarely in the eye. They looked back, munching on hay, nodding for their feed tubs, making all the smells and sounds that they always do. “Yes,” they told me emphatically, “I will take that peppermint.”
THIEVES GUILD

And that’s the reality, friends. They are horses. I love them all; I’m proud each time they run, regardless of the outcome. But I believe in them, too. We’ve taken our time with them; I know their personalities and their talent. We might occasionally be guilty, like every doting parent, of overestimating their abilities. But this game will teach you to take defeat in stride. Though we swallow the bitter pills we must, we still crave the sweetness of a win.
THIEVES GUILD

So, what’s it like to win a stakes? I have no idea how it plays out in the cool heads of the seasoned professionals. For us, it was like trying to keep a lid on a boiling pot. When we sent Thieves Guild out in the Caress Stakes at Saratoga on Sunday, we breathed the nervous exhale of cautious optimism we always do on race day. She is something special, but they all are.
THIEVES GUILD

In the paddock, she looked stunning. Ours always do. It’s one of the benefits of having a consummate horseman as your trainer. Jimmy Toner never turns a horse out looking poor. Jim’s assistant Tiffany had taken great care in braiding her mane and buffing her coat so the dapples shone. Her groom smiled as he walked her in slow turns by tree number 5. We all were smiling, but not confidently.
When we got to the box our hands were busy: Justin texted, Jim adjusted his binoculars, I paged through the program looking for clues. I glanced at the board: Are we really 2-1? We’ve never been 2-1 in a stakes. What’s taking so long? Why aren’t they at the gate? Four minutes to post? A lifetime.
THIEVES GUILD

Finally, the field entered the gate. The bell rang and I was grateful I only had to wait 5 1/2 furlongs. “Just make me proud girl,” I said, knowing that’s the only outcome.
Into the turn, she’s going :21, at the half, :43. Too fast, easy, easy. The fractions were worrisome. I feared they’d gobble her up.
Then, midway through the stretch, she kicked clear. (She kicks clear!) Before she crossed the wire, my jaw dropped. I realized that it has happened and the people around me made it happen. I hugged Jim’s daughter, Catherine, then Jim. Then l looked at Justin, my husband and partner in this crazy game, and almost cried: We did it! No crying, we won! Act like you’ve been here before. Where’s the winners’ circle? How do we get there?
We fumbled our way down the stairs, trying to find the right path. Friends congratulated us. We nodded and smiled, and I just keep looking back at Justin. Are you with me, kid?
As we walked into the winner’s circle, it felt like an arrival at a red carpet premiere. Guards on either side cleared a path and welcomed us in with smiles and congratulations. Our names were announced, people shouted. Where do I put my purse? Where’s my horse? There’s a trophy. Can I put my purse next to the trophy? Is that weird? Yeah, that’s weird. I’ll put it on the ground.
Justin told me to walk the horse in. What? My inner monologue stammers. Wh- Walk? Feet? Horse?
“No,” I told him, sheepishly, “I’m ok.”
“Oh you HAVE to,” he insisted like a veteran, “You’re gonna remember that forever!”
I hesitated. The track photographer took the lead and told Jim I was going to walk the horse in. I held onto her and we walked ourselves into the Saratoga winner’s circle. Snap snap. Is everyone here? Trophy time: snap snap.
The fanfare ended almost as quickly as it arrived, though perhaps it lasts a little bit longer than the blistering minute and four-fifths of a second it took to cross the finish line first. The text messages came in, first congratulatory, then questioning. “What’s next?”
It was far too soon for that, though. It was time for a drink, maybe a couple, and a few hours of pure immersion in the moment. We stayed for six more races and can’t name another horse that ran. This was Thieves Guild’s day, and one of the best days of my life.