Oliver Cromwell’s 16.605 at the 2024 Pink Buckle changed the game for Kaiden Ayres, and it’s been a whirlwind adventure that led to more than $100,000 earned in less than a year’s time in the barrel racing arena.

California barrel racer Kaiden Ayres was the surprise of the 2024 Pink Buckle when she blasted a 16.605 to win the second round of the $925,000 2D Futurity aboard her “diamond-in-rough” Oliver Cromwell.

Not only did their time top the Futurity round, but it also won the second round of both the Sale Graduate Futurity and Open, the Owner/Rider Sidepot as well as the Premier Pink Sidepot for first competitors. It was also good enough for second in 1D of the $1.375 million Open. 

That one run was worth $73,475, including the stallion owner’s and breeder’s share.

“It was life changing for sure,” the 23-year-old from Woodlake said.

Ayres, an all-around hand who was born into a family of team ropers, started dabbling in the futurity world during the doldrums of the COVID shutdown. With no rodeos to attend and her college plans on hold, she purchased her first two greenly started futurity colts, finished them out and campaigned them. 

“I fell in love with it as I learned about the process and what it takes, training colts and watching them progress,” she said. “It was really fun learning with the two of them because they were so different. I was just learning so many new things. The futurity world is so huge, and I was learning how much money there was out there (to win). I was just taken aback by all of it.”

Kaiden Ayres’ mother actually stumbled across Oliver’s advertisement on The Premier Horse. Although she wasn’t instantly impressed, she was intrigued by the 2019 gelding, by Tres Seis out of the graded stakes winning Dash Ta Fame mare Dash Ta Moon, a half-sister to racing champion and National Finals Rodeo sire First Moonflash. 

Bred by Bobby and Catherine Simmons, Oliver had run on the track for the Simmons and partner Johnny Trotter. He won a race and placed twice in eight starts—mostly futurity and derby trials—earning $16,602 and a high speed index of 92. 

The Simmons put Oliver in barrel training with Lance Graves, and he eventually sold at the 2023 Pink Buckle Sale. Todd Trask had purchased the gelding for a mere $14,000 and had him with Lacey Donegan when Ayres made an offer on the gelding after seeing his ad in May 2024. 

After a few attempts at home and one run at jackpot resulted in disaster, Ayres decided to switch Oliver from the right-barrel first to the left. For the entire month of June, Ayres trotted the pattern every day and focused on repositioning his feet.

“I’m lucky he’s as smart as he is because I don’t know if another horse would have been as open to changing his style,” she said. “He feels like a completely different horse. I think a lot of credit has to go to him for being so smart and willing to change. I don’t think a lot of horses a like that.”

In July, Oliver made his first runs to left. They were slow but he showed that he was willing.

“Oliver just kept doing his thing,” she said. “I never put any pressure on him. I took him to his third jackpot, second to the left, and he was a 17.7 on a (WPRA) standard (pattern), and I was just ecstatic! I thought he was getting super confident.”

They had a small setback at the Royal Crown Race in August.

“That’s when I realized this horse might be a little more fragile than I realized,” Ayres admitted. “It scared him. He didn’t like the atmosphere. He didn’t like the setup. I had to backtrack again after Royal Crown because I scared him.”

Oliver was back on track by the Nampa (Idaho) Xtreme Mini Million in September, placing in the 2D with a 17.5 on a WPRA Standard.

“I just kept letting him figure it out on his own,” she said. “I wasn’t going to jam on him or put pressure on him. I was going to let him show me when he’s ready.”

By the time the West Coast Barrel Racing Finals rolled around at the end of September, Oliver was finding his groove. After catching a barrel the first round, they posted the fastest time of the event to win the second go.

“I don’t hardly kick this horse,” she said “I just put my hand down and let him work. He ended up running the fastest time there by two or three tenths. It was crazy! He blew them out of the water!”

Ayres had entered Oliver in the Pink Buckle thinking that she had a shot at 2D money and sale sidepots but got more than she expected. 

“I rolled in there a little more confident, but I still wasn’t sure of what I was going to get,” she said. “I messed him up and hit a barrel in the first round, but he still had a good time. I remember talking to a friend that night—I still have the texts. I told her I feel something. I feel like there’s a 16.7 in there.”

What she felt was the second fastest time of the entire event behind Kay Blandford and 10-year-old Born Ivory James’ 16.531.  

“I remember being overwhelmed with emotion,” Ayres said. “There was this thought in the back of my head, ever since I switched him to the left, that there was something there. I was just waiting for it to come. When it finally did, I was just a wreck.

While the money she won was super helpful—she purchased her first horse trailer—it was the connections she made, especially with Oliver’s breeders, that made Pink a life-changing event.

“More so than the money were the connections it brought me,” she said. “It was eye opening. It was also the realization that I could make a living doing this. I felt like I was on the right track. It also opened some doors with Catherine and Bobby. They are letting me train a 3-year-old half-sibling to Oliver.”

Ayres’ next goal was to get Oliver across the $100,000 mark. And in mid June 2025, they crossed that mark and are still climbing. Head to QData to keep up with Cromwell’s earnings.