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Filly Friday: Good Cheer wins the Kentucky Oaks 2025

Racehorses on a muddy track
Giselle Rhoden
/
LPM
Texas residents Valerie and Jay Freeman say they've been coming to the Oaks for the last four years.

Good Cheer, the heavy favorite, is the winner of the 2025 Kentucky Oaks.

After nearly a full day of sun, rain hit Churchill Downs shortly before the Oaks race.

That didn’t stop Good Cheer, who charged in the final stretch and beat out a dozen other 3-year-old Thoroughbred fillies on a recently-muddied track. Along with jockey Luis Saez, Good Cheer finished the 1-⅛-mile race in just over 1 minute and 50 seconds, according to the unofficial time provided by broadcaster NBC.

Longshot Drexel Hill and and Bless the Broken followed in second and third place.

Trainer Brad Cox, a Louisville native, notched his third Oaks win with Good Cheer.

“She’s awesome,” Cox said after the race, citing her perfect record. “Seven for seven, she’s a perfect cheer.”

A colorful experience

Earlier in the day, as spectators prepared for the main event, they sported their best pinks for the Run for the Lillies.

Thousands of people from all over are in Louisville for a weekend of horse racing, bourbon, Derby hats and fashion.

Valerie and Jay Freeman from Farmers Branch, Texas at Oaks Day 2025.
Giselle Rhoden
/
LPM
Texas residents Valerie and Jay Freeman have been coming to Oaks for the last four years.

Valerie and Jay Freeman are from Farmers Branch, Texas, about 30 mins from Dallas. The two are part of a Texas-based horse racing group.

“I never miss an Oaks,” Jay said, tipping his bright pink fedora.

The Freemans said they consider themselves horse-racing aficionados, but Valerie said there’s more to see at Churchill Downs than fillies.

“The people-watching is over the top,” Valerie said. “Even the men like Jay like to dress up, and it's really fun to people-watch.”

Jovan and Brittany Fleming returned to Louisville for Oaks and Derby. The husband-and-wife duo live in Atlanta and are Louisville natives. They said they decided to stray from the traditional pink for Oaks Day and wear green from head to toe.

Louisville natives Javon and Brittany Fleming at Oaks Day 2025
Giselle Rhoden
/
LPM
Jovan and Brittany Fleming said they're hoping to win big on their Oaks bets.

Brittany said her color scheme represents wealth, prosperity and good luck.

“We want to win some money here today,” Brittany said. “Usually, if the name sticks out to me, I'm going with it. We did that last year and won $700! It was like a $20 bet.”

For Jovan, there’s more at stake than the races. He owns a cigar company called Kapito’s Way.

“It's just a good time and networking,” he said. “You never know who you’ll meet.”

Sydney Ecker is sporting a hat she made herself. Ecker — a Michigan native — started her millinery shop Eckuine Creations this year.

Jaylynn Montgomery-Lewis (left), Sarah James (middle) and Sydney Ecker (right) at Oaks Day 2025
Giselle Rhoden
/
LPM
Jaylynn Montgomery-Lewis (left), Sarah James (middle) and Sydney Ecker (right) at the 2025 Kentucky Oaks.

Jaylynn Montgomery-Lewis and Sarah James are hoping to give back to the community at Oaks. The two are Miss Kentucky winners and are selling raffle tickets at Churchill Downs. Half the proceeds will go to different charities around Louisville.

“We are here on behalf of the Miss Kentucky Scholarship Organization pageant, which offers us amazing opportunities like these to be in places like this,” Montgomery-Lewis said.

James said coming to Churchill Downs in person is a dream come true.

“I've always watched it on TV because I live in Lexington, so I usually just go to Keeneland, but seeing all the outfits in person and actually seeing the horses race has been phenomenal,” she said.

Post time for the Oaks is 5:51 p.m. The 1-⅛ mile race has a $1.5 million purse, most of which goes to the winner.

This story will be updated.

Giselle is LPM's engagement reporter and producer. Email Giselle at grhoden@lpm.org.

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