It’s a feat only four trainers in history have ever managed. But with three horses across the Kentucky Oaks and Kentucky Derby, Bob Baffert was hoping to become the fifth. After all, records tend to fall in front of the 73-year-old, but then tragedy struck, leaving Baffert not just bamboozled but rather unhappy with the result.

Baffert entered the 2026 Kentucky Oaks with Explora, a 7-1 favourite to win it all. Only Todd Pletcher’s Zany (4-1) had better odds going in. Explora was scheduled to start from the No. 1 post position. “You know, one hole, it’s always… I hate to have it, but you know, we’re stuck with it,” Baffert said in an interview with FanDuel Racing before the race.

“But, if she can get away clean, and if she gets in a good rhythm, I think she’ll be real tough.”

And Explora definitely got away clean. She blitzed the early lengths, setting fractions of 23.08, 46.85, and then 1:10.78 with only a few fillies able to keep up. One of them was long-shot 30-1 Brittany Russell’s Dazzling Dame, who, shockingly, kept pace with Explora. But the filly eventually stepped off the pedal, which allowed Michael McCarthy’s Meaning (5-1) to make her move.

And she kept pace with Explora, gradually wearing down Bob Baffert’s horse. Not quite what the six-time Kentucky Derby winner wanted to see, especially with Always a Runner charging them down. Chad Brown’s filly had kept a consistent pace from the get-go, which comes as no shock. After all, she entered the race having won the G3 Gazelle Stakes and the Maiden Special Weight.

Not quite big-ticket races, but she did it amid tough competition. Thus, it comes as no surprise that Always a Runner was keeping pace with the leaders, and then she made her move. Coming up on the final turn, the filly used every ounce of speed she had, passing both Explora and Meaning. And for Baffert, that’s when tragedy struck as Explora ran out of steam in the Kentucky Oaks.

All he could do was watch Chad Brown’s filly finish first, Meaning second, and Counting Stars third, while Explora crossed the line in fourth. It marks her worst career performance, as before this, Explora had never finished outside second place. That includes the G3 Honeybee Stakes, the Santa Ynez Stakes, the Maiden Special Weight, and several other races.

It marked a poor end to the race for Baffert, but for Chad Brown, it could be the start of something special.

Chad Brown reflects on Always a Runner winning the Kentucky Oaks

In 2025, Chad Brown’s stable was hit badly, and that includes his 2026 Kentucky Oaks winner. Like many horses in his stable, Always a Runner had been hit by a serious case of pneumonia. But things took a rather dangerous turn for the filly as she was on the brink of death. 

“This filly was struggling,” Brown told ESPN. “Her career was really up in the air.”

But then her situation changed after Brown and his team ensured that she got the best treatment. That included more than a month in a veterinary clinic and treatment in a hyperbaric chamber. It meant that she wouldn’t be able to race as a two-year-old filly, only making her racing debut a year later.

And fortunately for Brown, Always a Runner thrived. She won her first two races, the Maiden Special Weight in early February and then the G3 Gazelle Stakes in early April. The three-year-old filly finished both races ahead by more than a 1¼ lengths, showing exactly what she could do. And nobody was prouder than Chad Brown when she crossed the finish line in first.

“This filly is very resilient, very tough,” Brown said, according to ESPN. “She didn’t have to be here today. She didn’t have to run again. She could never have run easily.

“I’ve had it happen with several horses. The fact that not only did she overcome it and end up here today as an undefeated horse in the Oaks is just remarkable.”

But now, Chad Brown’s focus turns to the Kentucky Derby. Much like the Oaks, Brown has only one horse, Emerging Market, in the running, and all eyes will be on him. Because what Bob Baffert was trying to do will now be Brown’s to lose. After all, he could become only the fourth trainer in the history to win both the Kentucky Oaks and Derby in the same year.

The last trainer to do it was Kenny McPeek in 2024 when he won the Oaks with Thorpedo Anna and then the Derby with Mystik Dan. Before that, Ben Jones managed it twice in 1948 and 52, HJ Thompson did it in 1933, and James Rowe Sr. in 1915. Only time will tell if Brown manages to do it, but the odds are not in his favour with Emerging Market given 20-1.

Then again, Always a Runner entered at 10-1, so the odds don’t always tell the full story. For Baffert, though, the Oaks only reinforced his frustration with a race that slipped away from the worst possible spot, leaving him to regroup quickly with the Derby still to come.