The saga of Cruisewithbrandon might best be summed up in one statement: What's meant to be will always find a way.
Before she ever made it to the races, the daughter of Colonel John went through the sales ring four times. Bred in Pennsylvania by Brian O'Rourke and Derry Meeting Farm, she was the 2012 foal of the Tale of the Cat mare Baby Lets Cruise.
As a weanling, Cruisewithbrandon went to the Keeneland November sale and sold to Giddy-Up Ranch for $26,000. Ten months later, Paramount Sales offered her at the 2013 Fasig- Tipton Midtlantic fall yearling sale at Timonium, Md., and doubled her Keeneland price to $52,000. Not finished with the auction ring, she twice went to Florida's Ocala Breeders' Sales Company as a 2-year-old in 2014. She failed to meet her reserve in April and two months later brought $45,000 from John O'Meara.
She made her debut at Parx Racing Sept. 30, 2014, for trainer Louis Linder Jr. and Bran Jam Stable and David Clark, her owners for all 21 starts. Breaking her maiden in her second outing, she spent the next four years in allowance and claiming events from Laurel Park to Belmont Park.
Her second and final win came at Penn National July 7, 2016. Her final start came more than two years later, Sept. 28, 2018, and she was retired after a dismal try that spurred the Equibase chartcaller to note that she "drifted four wide into the stretch, then ventured onward to the finish line, placed to a protective hold." With a record of 21-2-2-2
and $75,643 earned, Cruisewithbrandon was retired.
Her owners placed her with Turning For Home, the aftercare non-profit run by the Pennsylvania Thoroughbred Horsemen's Association, Parx Racing management and the Pennsylvania Horse Breeders Association. She was adopted but later returned to the program, and was sent to the Giangiulio family's Castle Rock Farm in Unionville, Pa.
Managed for the past 31 years by June Hillman, Castle Rock is part of Turning For Home's 22-farm network. There, Cruisewithbrandon crossed paths with Hillman's son, Jason Hillman.
"She had gone through another partner farm that had put her somewhere prior and she ended up just sitting in like a backyard for about a year," Jason said. "They decided she wasn't the right horse, and they didn't have the means to take care of her the way they wanted, so they returned her to the program and she came to my mom. Mom offered Brandon to me just as a casual hack-around ride. That's when I first started riding her."
Jason, 33, moved to Castle Rock with his parents when he was 2 years old. He grew up showing his pony "with moderate interest" before gradually becoming more involved in "teenage boy stuff " as he got older. At Unionville High School, he and a friend learned that the school had a polo team as a club sport.
"We thought, 'All right, let's give that a try.' We joined the polo team and ended up playing interscholastically through high school. We got to go to Cornell University, University of Virginia, we played all over the place."
The friend played in college and Jason joined some professional teams in Florida as a groom and playing in practices. He also developed a serious interest in becoming a farrier.
Realizing he would not make a living playing polo, he enrolled in Heartland Horseshoeing School in Missouri. Initially, he considered shoeing as a source of income while he continued to play polo.
"After going to school and riding with some full-time farriers, I got so interested in it that I really buried myself in the blacksmithing side of everything," he said. "As I started to lean away from playing polo and that lifestyle, I delved deeper into becoming a farrier and got out of riding again for another five years or so."
He achieved his certification, dabbled in horseshoeing competitions, built his business and immersed himself in his profession, naming Andrew Neilson and Dave Werkiser as mentors. But before long, Jason began to feel that something was missing in his life.
"Even though it was giving me a ton of success and I was reaping a ton of benefits from it, I realized the riding aspect had been lost," Jason said. "I reached out to my mom and said I wanted to ride. Something away from work 24/7."
June Hillman put her son on Cruisewithbrandon. The original plan was for him to enjoy casual hacks and trail rides with the understanding that the mare would eventually be placed in a suitable permanent home. After a failed prepurchase exam -- a vet deemed her "unfit for even trail riding" due to an ankle chip -- June posted a for-sale advertisement for the horse. And Jason felt a gut punch.
"Oh my God, I can't actually let Mom sell this horse," Jason thought to himself. Then he talked to his mother. "Hey, I absolutely want this horse," he said. "I will buy her from you. I can't see her go."
At that point, Cruisewithbrandon could steer, but that was about it. The ankle chip proved easily manageable through maintenance.
"Knock on wood, she's been one of the soundest animals I've ever dealt with," Jason said. "She's held up amazingly."
With help from June and some riders who board at Castle Rock, Jason taught the mare to jump. While reluctant to even hop over logs at first, she soon caught on, and Jason discovered her natural talent. Their first competition came on a whim when they joined several Castle Rock horses and riders heading to an event at St. Augustine Pony Club in Warwick,
Md.
"I saw no reason why I couldn't do the starter [level]. I think it was probably a month out or so," he said. "I just real quick tried to learn everything I could to at least get around. I had never done a dressage test before, and I think we scored like a 45 percent. It went very poorly. I'm sure in show jumping she was charging around. But we made it over and I remember crossing the finish line and a couple people were there to greet me. And I remember one of the first things out of my mouth was, 'Is Plantation [Plantation Field in Unionville] still open?' I wanted to sign up for that."
Two weeks later, the pair competed at Plantation Field. Jason was hooked on eventing, and so was Cruisewithbrandon. Now in their fourth season, they finished the modified level last year and are pointing toward their first one star in 2026. Jason boards Cruisewithbrandon at Castle Rock and rides her four to five times per week. He works with Ashley Norris and credits his mom and fiancée Melanie Mills, a veterinarian, as his support group. Jason credits eventing with forcing him to find the right work/life balance, realizing that competing and progressing requires the same dedication he applied to shoeing horses.
And as for his horse?
"This mare is my friend. I don't think I would be confident doing what I'm doing with any other horse. We've learned together," he said. "Both of us were green. I didn't have much formal riding instruction, and she was the same deal. She learned with me, and it's been impressive to me how the partnership has grown. She's super bold, so she is willing to do anything. If I point her at something, I'm confident that she is going over it. Once she got a taste for this, it was like a light switched on in her head. 'Oh yeah -- this is fun! I want to do this!' She takes really, really good care of me."
