2023 Kentucky Oaks Replay | Pretty Mischievous Holds Off Gambling Girl Late To Win

Pretty Mischievous won the 2023 Kentucky Oaks (G1) at Churchill Downs after holding off a late charge from Gambling Girl. A Godolphin homebred daughter of Into Mischief, is the Brendan Walsh trainee now the top 3-year-old dirt filly in the world? Tell us YOUR thoughts in the Comments section!

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The track press release:

Godolphin’s homebred Pretty Mischievous held off a late charge from Gambling Girl by a neck to win the 149th running of the $1.25 million Longines Kentucky Oaks (GI) for 3-year-old fillies at Churchill Downs before a crowd of 106,381 on a sun-splashed afternoon.

Trained by Brendan Walsh and ridden by Tyler Gaffalione, Pretty Mischievous completed the mile and one-eighth over a fast main track in 1:49.77. It is the first Kentucky Oaks victory for Walsh and Gaffalione.

The victory was worth $767,250 and increased Pretty Mischievous’ earnings to $1,268,560 with a record of 7-5-1-1.

Pretty Mischievous is a Kentucky-bred daughter of Into Mischief out of the Tapit mare Pretty City Dancer.

Flying Connection led the field of 14 through fractions of :23.07, :46.96 and 1:11.28 with Defining Purpose to her outside and Dorth Vader three wide just behind the leader.

Gaffalione had Pretty Mischievous in the clear four wide and launched his bid on the far turn with a four-wide move that propelled her to the front at the top of the stretch.

Pretty Mischievous opened up on the field and had enough left in the run to the wire to hold off Gambling Girl, who had rallied from far back.

Pretty Mischievous debuted here last September with a 2 ¼-length victory sprinting 6 ½ furlongs and followed that up with an allowance victory going seven furlongs.

This winter at Fair Grounds, she won the Untapable Stakes and Rachel Alexandra (GII) before finishing second in the Fair Grounds Oaks (GII).

Pretty Mischievous returned $22.74, $10.10 and $7.40. Gambling Girl, under Irad Ortiz Jr., returned $12.84 and $8.36 and finished 2 1/2 lengths in front of The Alys Look, who paid $13.80 to show under Javier Castellano.

It was another neck back to favored Wet Paint, who was followed in order by Dorth Vader, Flying Connection, Defining Purpose, Mimi Kakushi, Wonder Wheel, Southlawn, Affirmative Lady, And Tell Me Nolies, Botanical and Promiseher America.

JOCKEY QUOTES FROM THE 2023 LONGINES KENTUCKY OAKS

Tyler Gaffalione, Jockey, Pretty Mischievous, winner: “It’s amazing. I feel so blessed. The trip worked out perfectly. I stayed out her way and she took me the whole way. What an incredible filly.”

Irad Ortiz Jr., Jockey, Gambling Girl, runner-up: “She ran great. I had no excuses. We just missed. Two more jumps and we would have got it.”

Javier Castellano, Jockey, The Alys Look, third: “I had a beautiful trip. I liked the way my horse ran. I sat behind the speed and saved all the ground on the first turn and then set up two-three wide on the backside. I travelled nice and comfortable. Turning for home, I thought I had a chance to win. She was a good third place today. She deserved it.”

Flavien Prat, Jockey, Wet Paint, fourth: “I got a good trip. It set up good for me. The track isn’t as fast as Oaklawn and I think she was struggling on a bit on it. She made a move but not as good as at Oaklawn.”

Luis Saez, Jockey, Dorth Vader, fifth: “My filly tried hard. She gave 100%. The track has been fast today and yesterday, we broke right there and were in a great spot. The winner at the 3/8th came in hand and I wish my filly was like that.”

Florent Geroux, Jockey, Flying Connection, sixth: “I stayed clean on the lead. She broke well but just couldn’t keep going and hold off the other fillies in the end.”

Mickael Barzalona, Jockey, Mimi Kakushi, seventh: “She ran well. She did the maximum. She gave it her best shot.”

Brian Hernandez Jr., Jockey, Defining Purpose, eighth: “She was moving well. The only negative is she got bounced around a little bit around the first turn and that got her into the bridle so she was a little keen. Going around the second turn I wasn’t able to put away the 12 (Dorth Vader), so she was always under pressure and it just got to her late.”

Joel Rosario, Jockey, Wonder Wheel, ninth: “He (trainer Mark Casse) wanted me to do something a little different. Take her back and then make one run. It looked like she was making a run but then she just steadied the last part.”

Rey Gutierrez, Jockey, Southlawn, 10th: “I was following Pretty Mischievous, and I thought I was in a great spot, following in the clear. I was so confident in her going into the race and it just didn’t work out.”

Rey Gutierrez, Jockey, Southlawn, 10th: “I was following Pretty Mischievous, and I thought I was in a great spot, following in the clear. I was so confident in her going into the race and it just didn’t work out.”

Ramon Vazquez, Jockey, And Tell Me Nolies, 12th: “I got a very bad trip—it was tough. I was lucky to not get knocked down in the first turn. After that my filly didn’t want to try any more.”

Chris Landeros, Jockey, Botanical, 13th: “She didn’t break as sharp as we wanted and got tossed around the first 50-60 yards but that’s racing. That’s the way it goes. Sometimes you have to go to Plan B. We found our stride and were comfortable running down the backside and I had a spot to go on with her. She didn’t take me there today. It’s back to the drawing board.”

Jorge Vargas Jr., Jockey, Promiseher America, 14th: “She’s a very nervous filly and right before we started loading in, she lost it a little a bit. The atmosphere here was pretty wild for us with her coming from Aqueduct. After that she was like ‘Not today.’”

TRAINER QUOTES FROM THE 2023 LONGINES KENTUCKY OAKS

Brendan Walsh, Trainer, Pretty Mischievous, winner: “This is the kind of thing you dream about, to win a Grade I, especially the Oaks at Churchill Downs, it’s a long way from Cork in Ireland. It’s indescribable, it’s exactly what we’re here for, and why these guys (Godolphin) breed these good horses, and why everybody works so hard.”

Todd Pletcher, Trainer, Gambling Girl, runner-up: “She had a really good trip. He (Irad Ortiz Jr.) saved ground most of the way, angled out and she put in a great run.”

Brad Cox, Trainer, The Alys Look, third, Wet Paint, fourth, Botanical, 13th: “It’s always hard when you have a heavy favorite and you can’t get the job done. But, at least two of three ran well. I need to take a look at the replay. I don’t really know what happened. Botanical didn’t get away very well. The Alys Look stayed on and ran really well. She got a good trip up the backside and was relatively close. Looks like you want to be close on this racetrack. Two of the three ran well. I have to go back and watch the replay to see what happened to Botanical. Flavien (Prat) said Wet Paint was traveling fine. He said when he cut her loose she wasn’t handling the track real well. She finished up off class and off heart. But, probably not her favorite surface. She was struggling with it. A very good filly won it. We had fillies finish third and fourth. They showed up to run.”

Michael Yates, Trainer, Dorth Vader, fifth: “She went pretty fast challenging on the lead and just got tired late.”

Todd Fincher, Trainer, Flying Connection, sixth: “She showed her guts. It was a very quick pace with pressure the entire way. Turning for home she continued to fight hard, but the pace took a toll on her. I’m very proud of her.”

Greg Geier, Assistant Trainer, Defining Purpose, eighth: “Like Brian (Hernandez Jr.) said, he could never get her comfortable. She got bounced around a little bit.”

David Carroll, Assistant Trainer, Wonder Wheel, ninth: “Honestly, we’re trying to digest the race right now, and will have to see what the jock says, and watch it again. Obviously, we’re disappointed, but we’re very proud of the race she ran.”

Norm Casse, Trainer, Southlawn, 10th: “It’s still pretty raw right now. I’m not sure where she finished. I haven’t even seen a replay. Watching it live it’s very difficult to see what happened. We had a little bit of a rough trip. It just wasn’t Southlawn’s day today.”

Graham Motion, Trainer, Affirmative Lady, 11th: “We didn’t have a great trip. A couple of the horses inside carried her out wide. We got shuffled back a lot further than we had planned.”