The trainer with a vast empire of horses entered five in Saturday's 139th run for the roses and, as bettors expected, Revolutionary, the colt guided by Calvin Borel, moved well over the wet track — but not well enough to catch winner Orb.
Borel had Revolutionary running at the end, but ultimately finished third. A three-time winner of the race — twice in mud — Borel had spurred bettors to make Revolutionary the favorite for much of the day.
"The only thing I could have done on the far turn was creep up closer on him," Borel said. "Turning for home, I still thought we had a shot to win but he gave me a good turn of foot."
Pletcher's Verrazano, an undefeated colt who many thought would be the morning-line favorite, finished 14th.
"We had a good trip," said jockey John Velazquez. "I just don't think he liked the track. He was already in trouble on the first turn when he was trying to get a hold of the track. He was kicking a lot and overworking to keep up."
Pletcher thought the fast early pace of the race also caused Verrazano trouble.
Velazquez, Orb's original rider, opted to ride Verrazano. That put Joel Rosario, one of the hottest jockeys in the country, up on Orb. Rosario was rewarded with his first Kentucky Derby win.
Rosie Napravnik, who began her career riding in Maryland, finished fifth on Mylute. She was making her second attempt at becoming the first woman to win the Derby. The fifth-place finish was the best finish in a Derby by a female jockey.
"We were right inside of Orb the whole way and I knew we were in good shape," she said. "We did have to go around but it was a clear run. It was an exhilarating feeling at the quarter pole knowing that I had a shot."
Fifty-year-old Gary Stevens also had a path to the lead as his horse Oxbow turned for the stretch, but the D. Wayne Lukas trainee finished sixth. The three-time winner of the Kentucky Derby returned to riding in January after an eight-year layoff, much of it spent working as a racing analyst. He was serene as he led his horse to the gate and jubilant after coming off the mount afterward.
"Coming into the stretch, I had a big smile on my face," said Stevens, who also worked as a reporter during the week. "I'm going to win my fourth. But five strides later, I was attacked from the outside for a couple strides, and they went on. He was brave ... I've still got a smile on my face. I can't wipe it off."
A day of firsts
Orb delivered a number of firsts for his connections. The owners, Stuart Janney III and Ogden Mills "Dinny" Phipps, trainer Shug McGaughey and jockey Rosario all had their first victories in the Derby.