Watching Rafael Weiss with his hands on the sides of his head, pushing his vocal cords to their limit as he urged longshot Ocelli homeward to a third-place finish in the 152nd Kentucky Derby, it's hard to picture this being a man who wanted out of horse racing just a couple of years ago.
But that's what grief can do to a man.
Weiss took over his family's Rosedown Racing Stables operation following the death of his father, the Boca Raton-based real estate CEO Jeff Weiss, in January 2024, and he wasn't sure sure if he wanted it. The elder Weiss brought his son into the sport, and they'd enjoyed success that took them to heights as lofty as starting gate stalls in the Breeders' Cup and inaugural Pegasus World Cup Invitational Stakes, back when the purse was a world-topping $12 million.
The Weiss family had a small broodmare band and an even smaller racing operation, and just four days after saying goodbye to his father, Rafael had to make his first major decision as head of the stable. In his mind, it could have easily been one of the last.
It was time to consider whether to keep any of their modest crop of Kentucky-based yearlings, born and raised at Taylor Made Farm in Nicholasville, Ky., or enter them for auction.
Among them was a crooked-legged colt sired by Connect who the younger Weiss liked more than his advisors did. Keeping any of the foals to race would have meant a long-term commitment to the industry, carrying those horses through training and hopefully years-long campaigns. Selling the youngsters and consolidating to strictly be a commercial breeding operation would have given the younger Weiss an opportunity to put at arm's length a part of his life that, at the time, reminded him of a painful loss.
He elected to sell.
"I was abandoning racing completely," he said. "I was really not trying to race anymore at all. I was just trying to breed and sell…I wasn't thinking straight at the time, that's for sure."
That Connect colt would become the classic-placed Ocelli in a few years' time, but in the summer and fall of 2024, he was simply a young horse whose commercial appeal was flagging with each check-in heading into October's Fasig-Tipton Kentucky Fall Yearling Sale.
His mother, the Scat Daddy mare Zalia, was purchased privately after finishing under her reserve at the 2018 Ocala Breeders' Sales Co. Spring 2-Year-Olds in Training Sale, and she showed promise winning on debut, but her career was cut short due to injury. Ocelli was her second foal, and her first, the Violence colt Red Thorn, was still a year away from racing, owing to a throat issue.
The produce record wasn't helping Ocelli's case heading into the final yearling auction of the season, but he didn't do himself any favors either.
"I look back at my texts and was looking through them and I said, 'Man, I like that Connect colt. He looks halfway decent," Weiss said. "My team, unfortunately, was telling me that he's a little bit turned out, this and that. He was very incorrect."
The market agreed, and the colt hammered to Legion Bloodstock for $12,000. Ocelli stepped out of the sales ring, another horse stepped in, and the day went on.
Between the stud fee, carrying costs, and the expenses to go to the sale, Weiss took a financial beating on Ocelli during their time together. At the time, though, the important thing was getting the horse off the books so Weiss could begin the process of moving on.
"I mostly breed to sell, so I see what happens with the market, and we just have to put them out there, and what the market gives us is what they give us," he said. "It doesn't feel good, obviously.
"I don't know what Legion saw or what faith they had, but they had some amazing foresight," Weiss continued. "There were other horsemen that were looking at him, but nobody took the gamble except them, and it paid off."
Jeff (left) and Rafael Weiss of Rosedown Racing StableCourtesy Rafael Weiss
Life went on for both Weiss and Ocelli. Weiss sent Zalia on dates with Early Voting and Mitole and came back with a pair of colts. He remained engaged on the breeding side, even retiring his Grade 3 winner Champions Dream to stud in Florida, but his presence on the racetrack was limited to just one horse: Ocelli's older brother Red Thorn.
In his day job, Weiss became CEO of JW Advance, his family's Florida-based commercial real estate development company, and branched out to found Sytes, a tech company that connects tenants seeking a property with potential developers and landlords.
Meanwhile, Ocelli was placed in the barn of trainer Whit Beckman for owner Ashley Durr, who was later joined in the partnership by Anthony Tate and Front Page Equestrian. Though the winner's circle remained elusive, the colt's connections kept giving him chances against high-level competition, even when it led to off-the-board finishes in the listed Sam F. Davis Stakes and Virginia Derby.
He came from way back to get a piece of the action in the G2 Wood Memorial, finishing third and giving him 25 qualifying points for the Kentucky Derby. That number looked well south of the line to even make it into the Derby program as an also-eligible, but he was never removed from consideration, and he made it to the Derby draw's waiting list through attrition. Two scratches from the main body of the field later, Ocelli was guaranteed a shot at the roses with jockey Tyler Gaffalione.
Bettors and prognosticators were justifiably unimpressed with Ocelli's credentials when they were forced to consider him after he scratched into the race. While the prognosticators (this writer included) turned up their noses, Weiss was too busy trying to navigating booking tickets and travel to Churchill Downs on short notice to see the horse he bred run in the Derby to pay attention to what people were saying about them.
"I was just shocked to even have that horse in the Derby," he said. "I couldn't even believe the fact that he was going there. I ended up buying tickets last-minute just to be able to go. Of course, everyone, says, 'Oh, the horse isn't meant to be there,' and this and that, and guess what? He earned his right. He did it."
Ocelli left the gate with the longest odds on the board at 70-1, and Gaffalione worked to steady his mount through the jostling that most Kentucky Derby runners experience during the race's chaotic opening jumps. He settled near the back of the pack and made his move in the final turn, getting past Danon Bourbon to assume the lead in the middle of the stretch for a few jumps before the winning exacta passed him battling down the middle of the track.
It was an emotional rollercoaster for Weiss, going from "happy to have a Derby starter, even if it's a longshot," to "my longshot is making a move in the Derby," to "the horse I bred might win the Kentucky Derby," to "the horse I bred just ran third in the Kentucky Derby at huge odds."
"I couldn't believe it," he said. "I literally couldn't believe it. I was excited. I know what this means for Rosedown Racing as a breeder, and what it would do for the family."
"The family" in this case means a few different things. The first is obvious. This is the business his father brought him into, and getting a horse to the Derby was one of the white whales the elder Weiss never got to bag.
As the colt crossed the finish line, the younger Weiss couldn't help but think of what his father would have done before, during, and after the race if he were there to see it.
"Oh my God, first of all, he would have killed a couple of our advisors over there at Taylor Made and down here (in Florida) who told us to sell the horse," he said. "Number two, he would have probably tried to buy back in at an exorbitant price, which probably would have been smart, honestly. He would have just been going crazy. My dad was a wild guy."
It also means a lot for Ocelli's family. Weiss had a show ticket on the colt, so he went a fair bit toward getting the breeder out of the red on his lifetime investment in the horse, but his real return on investment will come on the pedigree page, with all of his future brothers and sisters that are sent through the auction ring being a sibling to a classic-placed runner.
Ocelli's dam Zalia has already redeemed her commercial momentum, with her Early Voting colt selling as a yearling last year for $475,000. Now a 2-year-old, the colt is currently in the barn of trainer Cherie DeVaux, who conditions Golden Tempo, the horse that passed Ocelli to win the Derby.
Zalia lost her Newgate foal during the 2026 foaling season, and she was sent back to Early Voting for 2027.
That leaves Zalia's yearling Mitole colt, and a decision to be made about the future.
Weiss had made the decision a few years ago to focus on commercial breeding, but watching Ocelli nearly get the job done on the biggest stage, and the thought of what his father would have done with the horse had he still been around, has the younger Weiss taking a moment to consider his options.
This time around, the decision comes out of joy, not grief.
"After everything, I just don't know if I want to sell him," Weiss said. "I think I might have to take a shot. As much as I try to maintain discipline, when you see something like that, it's really hard to, stick to selling these horses.
"I won't sell him for $12,000. I'll tell you that right now."
This story was originally published by Paulick Report on May 5, 2026, where it first appeared in the News section. Add Paulick Report as a Preferred Source by clicking here.
