The following year, the turf course was built and the condition book and nature of Colonial Downs fundamentally changed. It worked out well for Victory Gallop, whose Belmont Stakes win, in a hypnotizing photo finish, foiled Real Quiet’s Triple Crown bid.

Plenty of horses have raced at Colonial Downs as three-year olds after Kentucky Derby starts, testing the turf after running on the dirt of Triple Crown, usually targeting the Virginia Derby. The longstanding Colonial-to-Derby drought made sense, though, as Colonial sometimes ran over 90% of its races on the turf..

With the reopening of Colonial Downs in 2019, Jill Byrne, then Colonial’s vice-president and director of racing, wanted to utilize what she considered an undervalued asset, Colonial’s dirt course. Byrne and racing secretary Alison De Luca started to mix more dirt contests in race cards, and last summer dirt races were regular feature; one card even included more dirt than turf races.

Trainer Larry Rivelli had made his first trip to Colonial Downs after the closing of Arlington Park, which left Illinois without live racing during that time of year. Colonial became an attractive option to Rivelli, who was the leading trainer of Arlington’s last eight seasons, and other Illinois horsemen. 

“Colonial was a fantastic place for us to be at least last year,” said Rivelli. “We shipped most of my stable there.”

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Speaking of which, last July 18, Colonial’s first race of the day was a $62,000 Maiden Special Weight for two-year-olds going six furlongs on the dirt. That’s where jockey Jareth Loveberry first teamed up with Two Phil’s, a maiden breaking score by over two lengths.

“We were just hoping to have a nice horse and was working through the progression of breaking the maiden and such,” recalled Rivelli. “He actually had a bad trip and ran sneaky good. Jareth gave us input after the race. He said he liked him more much now than before.”

Two Phil’s progression continued as he won the Shakopee Juvenile going six furlongs at Canterbury Park in September. In his first attempt at a mile and a sixteenth, he finished seventh in October’s Breeder’s Futurity (G1) at Keeneland, a race won by Forte. Despite the setback, his speed figures moved forward once again. 

Later that month, Two Phil’s won the Grade 3 Street Sense at Churchill Downs over a sloppy racetrack and Rivelli’s thoughts got bigger.

“After winning the Street Sense, we knew that this horse could really be something special,” remembered Rivelli.

Without winning, Two Phil’s’s rise continued in stakes races at the Fairgrounds. He finished second in the Lecomte Stakes (G3) and third in the Risen Star Stakes (G2), improving figures with each start.

“Numbers-wise and maturity wise, he’s definitely progressed in every race,” observed Rivelli on Off to the Races Radio prior to the Risen Star stakes in March. “Usually when you stretch them out their numbers tend to go backwards a little bit, but he’s continued to go forward and he’s maintained soundness. He’s a very smart horse. He doesn’t sweat the small stuff, which I like.”

That progression eventually resulted in a win in Two Phil’s’s next start in the Jeff Ruby Stakes (G3) at Turfway Park. After the change of venues – and change to synthetic surface – Two Phil’s won by more than five lengths. He again improved his speed figure, but more importantly, he also earned enough points to get him into the Kentucky Derby starting gate.

It’ll also be Loveberry’s first Derby mount. Rivelli doesn’t have any reservations about staying with his  jockey riding in his first Kentucky Derby. Instead…

“If you’re driving a Corvette and I’m driving a Pinto, I may be the best racecar driver in the world but you’re going to beat me every time,” acknowledged Rivelli. “He’s skilled and experienced; he just hasn’t been on this kind of dance floor before.”

Two Phil’s is by Hard Spun out of the General Quarters mare Mia Torri, a homebred for Phillip Sagan, who owns the horse in partnership with Rivelli’s Patricia’s Hope LLC.

“We’re a tight-knit group. We stay loyal to each other, which makes this experience much more special,” praised Rivelli. “He went to Colonial because I went to stable at Colonial.”

So, sure, Saturday’s Derby will be the first for trainer and jockey, and the biggest stage yet for their horse. And Victory Gallop’s Colonial-Derby act is a tough one to follow. But it’s already a winning day for Team Two Phil’s.