Pretty Mischievous stalks the whole way, then scores a Kentucky Oaks upset

Pretty Mischievous topped a 14-horse field to capture the 149th running of the Grade 1 Kentucky Oaks on a sun-splashed Friday evening at Churchill Downs in Louisville.

Trained by Brendan Walsh and ridden by Tyler Gaffalione, Pretty Mischievous stalked for most of the race on her way to emerging victorious in the 1 1/8 mile race for 3-year-old fillies, which was run on a fast dirt track.

The victory, at 10-1 odds, represents the first Kentucky Oaks victory for both Gaffalione and Walsh.

The Oaks offered a $1.25 million purse.

Pretty Mischievous held off Gambling Girl (13-1) in the stretch to win by a neck, with The Alys Look (30-1) finishing in third.

“This is the kind of thing you dream about, to win a Grade 1, especially the Oaks at Churchill Downs,” Walsh said. “It’s a long way from Cork in Ireland. It’s indescribable, it’s exactly what we’re here for and why (Godolphin) breed these good horses, and why everybody works so hard.”

“I can’t even put it into words,” Gaffalione said in a postrace interview with NBC Sports. “She’s a tremendous filly and she showed it today.”

Earlier this spring, Gaffalione won his second consecutive Keeneland Spring Meet riding title, and his fifth overall.

Wet Paint, the overwhelming race favorite at 8-5 odds, sat behind the pace in mid-pack for most of the race, and never factored into the finish. Also the morning line favorite for the race, she finished fourth.

Louisville’s Brad Cox was the trainer for The Alys Look (third), Wet Paint (fourth) and 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,” Cox said, adding that jockey Flavien Prat said Wet Paint traveled fine during the race.

“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.”

Flying Connection established herself as the early pacesetter in the race before the turn for home featured horses going four-wide.

Pretty Mischievous was on the far outside of this four horse pack, before establishing herself as the leader and moving down the middle of the track closer to the rail.

Gambling Girl — trained by Todd Pletcher and ridden by Irad Ortiz Jr. — rallied late to make it a duel between herself and Pretty Mischievous in the closing furlongs, but ran out of time at the wire.

Pretty Mischievous left from post position No. 14, the furthest post used in the race. She went into the first turn three-wide, but quickly settled into a comfortable fifth place behind the lead of Flying Connection as she hit the backstretch.

“She broke alertly, put herself in a great spot. She got in a good rhythm down the backside,” Gaffalione added in a later interview with TVG. “I just kind of let her keep building on that … She had just enough to hold (Gambling Girl) off.”

The horse now holds a 5-1-1 all-time record in seven career starts. The victory was worth $767,250 and increased Pretty Mischievous’ earnings to $1,268,560.

She’s spent her whole career racing at either Churchill Downs (3-0-1 record) or Fair Grounds (2-1-0). She was both bred and is owned by Godolphin.

The payouts from this year’s Kentucky Oaks were sizable, given that three horses with double-digit odds finished in the money.

A $2 exacta of Pretty Mischievous and Gambling Girl yielded $403.14, and a $1 trifecta that included long-shot The Alys Look yielded $3,994.28.

Pretty Mischievous won the Oaks in 1:49.77.

Something indicative of just how much Friday’s Kentucky Oaks was dominated by long shots?

No horse with single-digit odds even ran in the top three of the race, at any point, from the first turn through the finish.

Pretty Mischievous was sired by Into Mischief, who is the sire for three horses set to run in Saturday’s 149th Kentucky Derby: Cyclone Mischief, Rocket Can and Sun Thunder.

Churchill Downs announced that attendance for Friday at the track was 106,381, which is a more than 6% increase from the 100,188 people that attended last year’s Kentucky Oaks Day.

This story was originally published May 5, 2023 at 6:08 PM.

Cameron Drummond

Lexington Herald-Leader

859-242-5257

Cameron Drummond works as a sports reporter for the Lexington Herald-Leader with a focus on Kentucky men’s basketball recruiting and the UK men’s basketball team, horse racing, soccer and other sports in Central Kentucky. Drummond is a second-generation American who was born and raised in Texas, before graduating from Indiana University. He is a fluent Spanish speaker who previously worked as a community news reporter in Austin, Texas. Support my work with a digital subscription