Pretty Mischievous overcame the outside post in a 14-horse field to win the $1.25-million Longines Kentucky Oaks with a sweeping rally under Tyler Gaffalione May 5 at Churchill Downs. (Eclipse Sportswire)
She broke from farthest outside in post 14, leading her to be three-to-four wide around the first turn. She was still taking the long way around turning for home in the demanding 1 1/8-mile contest, getting caught four wide as the crowd of 106,381 cut loose with a tremendous roar.
But then everything Pretty Mischievous had going for her on this sunny afternoon kicked in – a regal pedigree, a helpful change made by astute trainer Brendan Walsh, and an unflappable ride by jockey Tyler Gaffalione.
Gaffalione and Walsh celebrate the Oaks win. (Eclipse Sportswire)
All of that allowed Pretty Mischievous to fend off Mike Repole’s Gambling Girl by a desperate neck to provide owner Godolphin with its first triumph in the nation’s premier race for 3-year-old fillies.
“To win this race is unbelievable,” said Michael Banahan, director of bloodstock for Godolphin USA. “It is a tremendous achievement for everyone all around.”
The Godolphin homebred undoubtedly had pedigree on her side as she prevailed with a winning time of 1:49.77. She is a daughter of Into Mischief out of the Tapit mare Pretty City Dancer. “I think the Into Mischief speed and the Tapit stamina worked out really well,” Banahan said.
Still, bloodlines alone do not win prestigious races such as the Kentucky Oaks. Expert handling also is required, making the right decisions at the right time.
Walsh grew up on a small dairy farm in County Cork, Ireland. He was a teenager when he began his career with Godolphin. He has an innate sense of what horses want and need and he sensed that he needed to do something to help Pretty Mischievous focus just a bit more. Blinkers were the answer.
“I don’t know if it was a difference-maker,” he said. “But it definitely helped her finish the race.”
This was the first Oaks win for Walsh and Gaffalione. Banahan praised Gaffalione’s role in the breakthrough victory for Godolphin, a massive operation with bases in Dubai, Europe, Japan, and the United States for Sheikh Mohammed bin Rashid al Maktoum, prime minister of the United Arab Emirates.
“What a wonderful ride by Tyler Gaffalione after a very wide draw,” Banahan said. “He had to use all of the skills he has to get her in a great position. We are very grateful for the ride he gave her.”
The thrill of a Kentucky Oaks victory (Eclipse Sportswire)
Pretty Mischievous and Gaffalione most likely felt very much at home beneath the famed Twin Spires. The bay filly made a winning debut at Churchill Downs on Sept. 18. Gaffalione is a seven-time leading rider at the iconic track.
“I can’t even put it into words,” said Gaffalione, when asked the meaning of his first Oaks. “I’m so happy I was able to accomplish this, especially being in my home track now, Churchill Downs, and my family is here.”
Riders and their agents are often forced to make difficult calls when it comes to their mounts in major races. Gaffalione had enjoyed a magical ride aboard Wonder Wheel when she won the NetJets Breeders’ Cup Juvenile Fillies last November at Keeneland to end his Breeders’ Cup drought. But he left Wonder Wheel after the 2-year-old champion finished a perplexing sixth in the April 7 Central Bank Ashland Stakes at Keeneland.
He was always aware of the talent of Pretty Mischievous. “I have been on her since before she ever ran,” he said. “We have been able to develop a good relationship. Like I said, she gives me so much confidence. She’s a big, strong, beautiful filly.”
Many handicappers had expected the win to go to a different Godolphin homebred, Wet Paint, who had gone 3-for-3 at Oaklawn Park to begin her 3-year-old campaign. She is typically a closer from the clouds.
With the track playing for speed throughout the undercard, jockey Flavien Pratt positioned Wet Paint mid-pack. She lacked her usual tremendous closing kick for trainer Brad Cox and came in fourth, a neck behind third-place finisher The Alys Look, her stablemate.
“The track isn’t as fast as Oaklawn and I think she was struggling a bit on it,” Prat said. “She made a move, but not as good as Oaklawn.”
Pretty Mischievous won for the fifth time in seven career starts to go with a second and a third. With the lion’s share of the $1.25 million purse, her earnings spiked to $1,268,560. She paid $22.74, $10.10, and $7.40 across the board.
Jockey Irad Ortiz Jr. lamented what might have been in his bid to give owner Mike Repole his first Oaks victory with Gambling Girl. “She ran great. I had no excuses,” Ortiz said. “We just missed. Two more jumps and we would have got it.”
Repole also settled for second last year with Nest. He came make up for all of that if 2022 champion 2-year-old male Forte delivers as the favorite in Saturday’s Kentucky Derby Presented by Woodford Reserve.
