Trainer Ken McPeek may very well be in uncharted waters over the next eight days. The Kentucky-based McPeek will saddle classic runners in two of the most prestigious races in the world, with Daddys Lil Darling set to run in Friday’s Investec Epsom Oaks at Epsom Racecourse in England followed by Senior Investment’s planned start in the final leg of the American Triple Crown, the June 10 Belmont Stakes.

The transatlantic duo has been matched several times from the other side of the pond when Dermot Weld, Saeed Bin Suroor and Aidan O'Brien have sent horses to the American Triple Crown while maintaining their firm targets on the European classics, but McPeek is a pioneer among American trainers in aiming for the Epsom Oaks. 

Ken McPeek (Keeneland/Coady Photography)

He took on a similarly rare challenge in 2004 when he sent Hard Buck to compete in one of England's premier races for older horses, the King George VI and Queen Elizabeth Stakes, and came away with a solid second-place finish at 33-to-1 odds. 

Interestingly, Daddys Lil Darling, less than a month removed from a second-place finish on the dirt at Churchill Downs in the nine-furlong Longines Kentucky Oaks, also is listed at 33-to-1 for the Oaks at Epsom, to be contested over an additional three furlongs and on turf. 

"I don't know that I would call it thinking out of the box, but I like taking on challenges and trying new things," McPeek said this week from outside London. "In the worst case scenario, we will be learning something new. People are fearful of the unknown, and certainly when you are betting on horses you don't want to be wagering on the unknown, so I don't really put much weight on a horse's price for a race like this.

“I am looking at how the horse is doing and what she is cut out to do. The timing of this race, her stamina, and the way she has handled the grass, it all made sense for us to give this a shot. You take a good horse to a good race when they are thriving, and you have got a chance." 

Twenty-six years ago, a horse bred and based in New York achieved a breakthrough that is still unparalleled when Fourstars Allstar shipped across the pond and prevailed in the Irish Two Thousand Guineas at the Curragh. He remains the only American-based horse to win one of Europe's 3-year-old classics, which in each of the major racing jurisdictions of England, France and Ireland consist of a mile Guineas for both males and females, along with an Oaks and a Derby. 

"I am surprised that it hasn't been tried more," said Leo O'Brien, the Irish native who trained Fourstars Allstar. "If I had another horse good enough, I certainly would have gone again. My horse [Fourstars Allstar] had the ideal temperament for it. He was very laid-back and didn't mind where he was or traveling. When I suggested it to the owner at the end of his 2-year-old year, he said, 'What the hell is the Two Thousand Guineas?' But when I told him, he was gung-ho." 

Until Fourstars Allstar, Hard Buck more than a decade later, and the success of Wesley Ward trainees shipping over to Royal Ascot since 2009, racing's bridge between Europe and the U.S was virtually one way. European horses still ship over much more frequently than Americans going in the other direction. 

Daddys Lil Darling (Coady Photography)

"I wanted to run a horse, Java's War, in the Epsom Derby a couple years ago but the owner was against it," McPeek said. "To me, if you have a good horse that wants to go that far, why not try it?" 

McPeek figures that distance also is a favorable ingredient for Senior Investment's prospects in the 12-furlong Belmont, on the heels of a third-place finish in the 9 ½-furlong Preakness Stakes. The colt should be a much lower price than Sarava, who still represents the biggest upset in Belmont Stakes history when he scored at 70.25-to-1 odds for McPeek in 2002. 

"With the extra distance, he should be formidable, enough to make up the 4 ¾ lengths he got beat in the Preakness," McPeek said of Senior Investment, who captured the Grade 3 Stonestreet Lexington Stakes at Keeneland in April. "He is a really good horse who keeps improving, and I certainly think he has a better chance [in the Belmont] than I thought I had going in with Sarava."