Pretty Mischievous holds off Gambling Girl in Kentucky Oaks
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LOUISVILLE, Ky. – It's rare to make an equipment change in a race of the magnitude of the Kentucky Oaks. But trainer Brendan Walsh, with the full faith of owner-breeder Godolphin, added blinkers to Pretty Mischievous’s equipment for Friday’s 149th running of the Grade 1, $1.25 million filly classic, hoping to cure her tendency to wait on horses.
The move proved a difference maker, as Pretty Mischievous ($22.74) and jockey Tyler Gaffalione held off a charging Gambling Girl by a neck.
The victory, his first in the Oaks, was particularly meaningful due to Walsh’s long association with Godolphin. When he was just starting his journey in the Thoroughbred industry, he worked for the international operation as a rider in his native Ireland, and then in Dubai and elsewhere. When Walsh hung out his own shingle in the United States in 2012, they became staunch supporters. He won his first Grade 1 with homebred Maxfield in 2019, and has since trained horses such as multiple Grade 1 winner Santin under the Godolphin blue.
“They’re such a pleasure to work for,” Walsh said. “The guys were always on board with whatever we wanted to do. They were more than happy to let us [make changes]. They trust in you, and let you do what you think is right – there’s a reason they’ve got you working for them. That’s what makes them such a great operation to work for.”
Pretty Mischievous, a daughter of four-time reigning leading sire Into Mischief and the Grade 1-winning Tapit mare Pretty City Dancer, won her first two career starts at Churchill Downs in the fall of 2022, then was third in the Grade 2 Golden Rod Stakes in November before heading to Fair Grounds for the winter. She put herself atop that sector of the division by winning the Untapable Stakes by 3 1/4 lengths on Dec. 26, then the Grade 2 Rachel Alexandra Stakes by three-quarters of a length on Feb. 18.
However, in the Grade 2 Fair Grounds Oaks, the final race of that local prep series, on March 25, Pretty Mischievous cleared the field by 1 1/2 lengths in the stretch, but was reeled in late by Southlawn and beaten 3 1/4 lengths.
"At the top of the stretch, we thought she was going to win by five or six," said Michael Banahan, Godolphin’s American director of bloodstock. "She still had plenty to give."
Walsh thus thought it was time to add the blinkers, something he had considered for a while to help the filly focus her natural talent.
"She has that high cruising speed, and it's like it just comes so easy to her," Walsh said.
The Godolphin team and Walsh discussed the equipment change at dinner the night of the Fair Grounds Oaks and left that evening fairly confident in that plan. In the weeks leading up to the Kentucky Oaks, Pretty Mischievous breezed several times in her new blinkers. Gaffalione, who had been the filly’s regular rider – Brian Hernandez, Jr. rode her in the Fair Grounds Oaks as Gaffalione was riding the Dubai World Cup program the same day – was aboard for the works.
"We concentrated on the finish of her works, and her gallop-outs, and just getting her to finish up her works," Walsh said.
Pretty Mischievous drew post 14, in the outside of the full starting gate, for the Oaks. While Walsh was philosophical about the luck of the draw, Gaffalione was not displeased, feeling the space on the outside would allow him to get his filly settled in a comfortable rhythm early. When the gates opened Friday evening before a crowd of 106,381, Pretty Mischievous broke well, and Gaffalione settled her in fifth the first time beneath the twin spires.
"We were able to just kind of let her get out there and get her legs underneath herself," Gaffalione said. "She's a big, long-striding filly, and we didn't want to get in her way."
Meanwhile, just to the eventual winner's inside, Sunland Oaks winner Flying Connection (from post 10), Grade 1 Ashland Stakes winner Defining Purpose (11), and Grade 2 Davona Dale Stakes winner Dorth Vader (12), as expected, all headed for the lead, with Flying Connection the best of that trio by a length through an honest opening quarter of 23.07 seconds on the fast main track. In an unexpected development, Botanical, the front-running winner of consecutive stakes on the Tapeta at Turfway Park, was not involved early.
“She didn’t break as sharp as we wanted and got tossed around the first 50, 60 yards, but that’s racing,” jockey Chris Landeros said. “That’s the way it goes. Sometimes you have to go to Plan B.”
Down the backstretch, Pretty Mischievous continued to hold her position in the vanguard as Flying Connection continued up front through the half in 46.96 and six furlongs in 1:11.28 while coming under increasing pressure from Defining Purpose. Pretty Mischievous began to rev up in fourth, in the clear on the outside, and was pressing the leaders while still in hand at the quarter pole.
“I had a lot of horse around the turn,” Gaffalione said.
When Gaffalione asked for run, Pretty Mischievous responded and kicked away by three lengths with authority. But meanwhile, Gambling Girl, who had been a late-charging second in the Grade 2 Gazelle Stakes last month at Aqueduct, was again revving up for a big run. The filly was 10th after six furlongs, but when Irad Ortiz, Jr. tipped her out six wide nearing the quarter pole, she readily lengthened her stride and began eating into the ground.
It was much like the Fair Grounds Oaks – Pretty Mischievous was in a clear lead, and someone was coming. But this time, the filly kept her focus.
"Today, she went on off the turn," Gaffalione said. "So I was feeling pretty confident. I knew somebody was going to be coming, but I felt we had enough to hold her off."
At the wire, the final margin was a neck for the Godolphin filly.
"She produced a big run down the middle of the track, and just got there a jump too late," said Todd Pletcher, Gambling Girl’s trainer.
The final time for the nine furlongs was 1:49.77. She earned a career-high 92 Beyer Speed Figure for the effort.
After the top two, it was 2 1/2 lengths back to The Alys Look, who held off her Brad Cox-trained stablemate, favored Wet Paint, by a neck for third. Wet Paint, also a Godolphin homebred, had a three-race win streak in stakes at Oaklawn Park snapped.
“The track isn’t as fast as Oaklawn, and I think she was struggling on a bit on it,” jockey Flavien Prat said. “She made a move, but not as good as at Oaklawn.”
Wet Paint was fourth by a neck over Dorth Vader, with fellow pace influences Flying Connection and Defining Purpose next across the line. They were followed, in order, by Mimi Kakushi, last year's Eclipse Award champion juvenile filly Wonder Wheel, Southlawn, Affirmative Lady, And Tell Me Nolies, Botanical, and Promiseher America.
Godolphin, Walsh, and Gaffalione will look forward to teaming up with Santin on Saturday to chase a repeat victory in the Grade 1, $1 million Old Forester Turf Classic on the Kentucky Derby undercard. But for now, they were relishing in the “delight,” Walsh said, of their work with Pretty Mischievous coming to fruition.
“We've planned this for a very, very long time,” the trainer said. “Just thanks to everybody on the team, my team, that work for me. They did great work, tireless work. Michael and Dan [Pride, of Godolphin] and everybody in Godolphin who are just the greatest people to work for. Everything is discussed, and they're just a dream to work for.”
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