The good news is Jaywalk won last November's Tito's Handmade Vodka Breeders' Cup Juvenile Fillies (G1) at Churchill Downs and the Eclipse Award as the nation's top 2-year-old filly. The bad news for her connections—owners Leonard Green's D. J. Stable and Chuck Zacney and trainer John Servis—is she's trying to win the May 3 Longines Kentucky Oaks (G1).
It's a tough trifecta. Only two fillies have pulled it off in the last 30 years: Open Mind in 1988-89, and Silverbulletday in 1998-99.
However, Servis may have an edge: He saddled Zacney's Catherine Sophia to win the Oaks in 2016, and he's followed a similar prep schedule with Jaywalk.
Wintering in South Florida, Jaywalk made her 3-year-old debut in the March 2 Davona Dale Stakes (G2) going a mile at Gulfstream Park. The daughter of Cross Traffic tired, finishing fourth behind Jeltrin, and then made her way to Keeneland for the April 6 Central Bank Ashland Stakes (G1). In the Ashland she showed improvement, but was still third behind Out for a Spin and Restless Rider. Jaywalk remained at the Lexington track, not getting her first gallop over Churchill's main track until April 29. Later that morning, she drew post 7 for the Oaks.
In 2016 Cathryn Sophia won the Davona Dale and was third in the Ashland before winning the Oaks by 2 3/4 lengths.
"It's a process," Leonard Green's son, Jon said. "After Jaywalk won the Breeders' Cup, we knew we wanted to give her some time off. She'd earned it. We sent her to Hidden Brook South and got about six weeks of R&R. The end goal was always the Oaks; That's always been what we have been shooting for.
"John Servis has had a process in winning the Oaks with Catherine Sophia and we basically have gone along with that same plan that was successful previously. We all expected her to run a bit better in the Davona Dale, but the important thing was not how she ran in March, but how she'll run May 3.
"When we ran her in the Ashland, we were encouraged that she ran her race more like the ones she had previously. She ran a good, solid third. She lost by two lengths, but to two legitimate horses. Restless Rider is going to be the one to beat in the Oaks along with Bellafina coming in from California. We're just hoping Jaywalk is able to continue to improve and it will be her day come Oaks day."
Leonard Green runs an accounting firm that specializes in the horse industry. His son has his own financial planning firm. In the racing game for decades, D. J. Stable now has about 20 mares in Kentucky split among Taylor Made Farm, Hidden Brook, and Betz Thoroughbreds. The focus has shifted to quality with use of commercial stallions, while still shopping the yearling and 2-year-old sales for prospects.
Bred by Gainesway Thoroughbreds, Jaywalk was a $190,000 purchase from the 2017 Keeneland September yearling sale. By a first-year stallion, Jaywalk is out of the Orientate mare Lady Pewitt.
"We try to go to the Keeneland September sale with a criteria," Jon Green explained. "Horses have a certain amount of pedigree, and, of course, they have to have good conformation and vet clean. John Servis and Jim McGreevy head that team. Once they get together on a short list, we actually walk around with them and look at the horses. My father and I do a lot of the pre-work. Our goal is to get about six or seven horses out of that sale.
"After years of analysis, the Ocala Breeders' Sales April sale also gives us the best bang for our buck and we try to get between six to eight horses out of that sale," he continued. "The other sales are wonderful sales, but we've found if we have a certain amount of money to spend on a horse, we get a better buy out of these larger sales. The boutique sales are great to sell in, but tough to buy in."
With Zacney, D. J. Stable has been on quite a roll, and the hopes are for it to continue May 3.
"We've only been partners for two years and we've run in and won grade 1 races and we've run in multiple graded stakes with him between Diamond King, Jaywalk, Lucky Lee, and the list goes on," Green said. "He's a phenomenal partner and friend. When Jaywalk is running, the excitement is amped up even more because we get to do it with someone like Chuck."