After several months, he said, "I think it's time for you to start [competitive] riding," she recalled. "I was like, 'I am?' I couldn't believe he'd become as gung-ho as I was."
When she was 17, in June 2005, he finagled to get her onto Ringofdiamonds, a mount at Pimlico. She won and never looked back. Now 26, she's one of the best and most celebrated jockeys in North America and a winner of more than $63 million in purses.
With Boyce, Small used tough love. When she started as a rider at Pimlico, she said, she hadn't quite outgrown her youthful partying ways.
Every time she showed up late, he'd berate her in front of the whole barn. If the effects of a late night lingered, he'd put her on the roughest horses that day.
"He absolutely tortured me, and I'm sure he was chuckling inside," said Boyce, who has gone on to win 47 races and more than $11 million in purses in a five-year career. "He knew how to get his point across."
Small, a man who trained at least one stakes winner in all but one of his 40 years in the business, never claimed credit for his proteges' successes, Bowman said, though he quietly reveled in them.
That included the moment last year when the twice-divorced Small, who had no children, was in the hospital for treatment and Napravnik won a major race.
"I was with him, and I turned around and he had tears in his eyes," Bowman said. "He couldn't have been more proud of that girl if she was his own daughter."
Pimlico dubbed Friday the "Ultimate Girls' Day Out," using the common parlance for women at the track. The day featured the 90th running of the Black-Eyed Susan race for fillies, a lineup of vendors owned and operated by women, and speakers from the Susan G. Komen cancer foundation.
Infield vendor fees also went to Suited to Succeed, a local nonprofit that backs low-income women entering business, and for the first time, Saturday's main race features a female jockey (Napravnik), a female trainer (Linda Rice) and a filly (Ria Antonia).
Napravnik, third on the North American leader board in earnings for 2014, feels she has a "good shot" at upending Kentucky Derby winner California Chrome aboard Bayern, an outcome that would make her the first female rider to win the Preakness.
But for the first time since 1974, the man who got her started won't be there.
She and other legends will mourn Small today, but not in a maudlin way. That, Knight said, would diminish what he believed in most.
"Will I be thinking of Dickie?" she asked. "Probably not. My hands are going to be full just trying to stay on the racehorse. I can't think of him without crying, and my goodness, he'd never want that."