As she sat inside her office at Keeneland on the morning of April 13, everything around Shannon Ritter seemed to radiate calm.
Situated in Barn 1 away from the main track, Ritter's surroundings were among the most peaceful on the grounds with only the occasional rustle of hay as a disturbance.
The 45-year-old trainer and Minnesota native remained unfailingly unruffled as she spoke of the enormity of the situation she is facing. Ritter may be preparing for the biggest test of her career, but she is far from an ordinary newcomer to the Kentucky Derby scene.
On the evening of March 28, Ritter's life was thrown for the best kind of loop when her stable star, the WinStar Farm-owned colt Endorsement, rolled to a 3-length win in the Grade III, $800,000 Sunland Derby, earning himself and his upstart trainer a spot in the Kentucky Derby.
While the names Pletcher, Baffert, Zito and Lukas are commonplace in the entry box for the first Saturday in May, Ritter will be saddling her first Derby starter — a feat made more impressive by the fact the former jockey has been training on her own for only five years.
If Ritter seems to be taking it all in stride it's because she has first-hand knowledge of what she's in for. For seven years, Ritter was an assistant to former trainer and current WinStar Farm vice president Elliott Walden, and she counts Derby runners-up Victory Gallop (1998) and Menifee (1999) among the proteges she helped develop.
"It's kind of slowly sinking in," Ritter said of her Derby reality. "I think with all the people congratulating me and saying they're happy for me, that's kind of what is keeping me thinking that we're really going.
"It will definitely help being through it before and, because it's a WinStar horse, I'm still working with Elliott so it will kind of be like old times really."
Ritter has never been afraid to extend herself or test her abilities. From 1988 to 1996, Ritter carved out a solid career as a jockey, booting home 266 winners and earning the riding title at Portland Meadows for the 1990-91 season.
When she decided to shift from that side of the industry, Ritter literally walked into Walden's barn one day seeking a job. Shortly after becoming one of the stable's exercise riders, her horsemanship and determination allowed Ritter to ascend to one of Walden's lead assistants, even traveling to Dubai with Victory Gallop when he ran third in the 1999 Dubai World Cup.
"She was always a great worker, very dedicated and earned her way up to a role of traveling with the better horses," Walden said of Ritter. "She is really just a great horsewoman. I'm very comfortable with her because ... she's held my Derby dreams in her hands before when she was working with Victory Gallop and Menifee."
In 2005, the same year Walden stepped away from training to become WinStar Farm's racing manager, Ritter took all she had learned as an assistant and started building a stable on her own.
"It just started to where I needed to challenge myself to do more and so that's how I made the decision to go out and try it," Ritter said.
With her diligent hands-on style and riding background, Ritter often gets on her horses herself and is subsequently able to feel little nuances that might escape some of her brethren.
However, even with a modest-sized stable, getting on every horse every day is difficult.
"The real key for Shannon was to translate what she felt on their backs when she was galloping to what she could see as a trainer because you can't get on all your horses," Walden said.
"Elliott would always challenge me to watch them go because I always relied on just getting on them to see what I thought of them," Ritter added. "It works both ways. You can watch and see something you might not feel or you might feel something that you can't see watching them."
Ritter's steady development as a trainer is no shock to those familiar with her work ethic. The rise of her Derby contender, however, was more meteoric.
Unlike fellow WinStar-owned Derby hopefuls Rule, Super Saver and American Lion, Endorsement was under the radar at the start of the season having made just one start as a juvenile — finishing seventh in a 6-furlong maiden race at Churchill Downs last November under the care of WinStar's farm trainer Richard Budge.
Since joining Ritter, the chestnut son of Distorted Humor has blossomed in each of his three starts in 2010. After breaking his maiden third time out at Oaklawn in February, Endorsement executed a perfect stalk-and-pounce trip in the 11⁄8-mile Sunland Derby when he collared graded-stakes winner Conveyance in the lane en route to giving Ritter her first graded-stakes win.
"We were hoping for that kind of race," Walden said. "He was training well coming into it so we felt good about the whole situation."
If Ritter earns her second graded-stakes win a week from now, it would be an unprecedented milestone. None of the 12 female trainers to saddle a Derby starter has emerged a winner.
"I think about (winning) a little bit, but not too much," Ritter said. "I'm just focusing on the fact that gosh, we have a chance. And we do have a chance."