The Derby didn’t exactly turn out as Repole had hoped, as Uncle Mo became ill and never made the race, and his other contender, Stay Thirsty  , finished 12^th. If you haven’t heard Repole’s name much recently it’s not because he hasn’t been active—the New Yorker was a major player at both the Keeneland September yearling sale and the recent Ocala Breeders' Sales Company's select sale of 2-year-olds in training, and his smart claim Calibrachoa has won a couple of graded races at Aqueduct this winter. But being that it is Triple Crown season and that’s where most people are focused, Repole is no longer in the spotlight.

“Last year was a special year. I wasn’t naïve about it even as I was going through it,” Repole said. “I knew it was a once in a lifetime type of year to have two of the top 20 3-year-old colts in the country. I was thankful and appreciative then, and knew I may never ever get back to the Derby again. Looking back on it, even though I had a lot of fun going through the experience, it was pretty stressful.

“This year we also had high hopes. We had Overdriven  , who was undefeated as a 2-year-old but unfortunately got injured, and we had Giant Surprise  , who ran a 90 Beyer in his first race but also got hurt and is now breeding 75 mares in New York this year. That's how it goes. Now we have one more good one with Our Entourage. But he was a May foal and a late bloomer, so we’re going to have to see where he takes us.”

For Now, Our Entourage is taking Repole and trainer Todd Pletcher to the $500,000 Illinois Derby (gr. III) on Saturday, April 7 at Hawthorne Race Course, where he is expected to be part of a large field of mostly unheralded sophomores all in need of graded earnings in order to punch their tickets to the May 5 Kentucky Derby. Repole has had high hopes for the son of Street Cry ever since he bought him for $350,000 at the Keeneland September 2010 yearling sale, but because he is out of a Dynaformer mare and after seeing how he has trained and raced, his preferred surface is turf.

Both of Our Entourage’s wins have come on turf, including a one-length optional claiming score Feb. 25 at Gulfstream Park, but because it is that time of year Repole and Pletcher have decided to try him again on dirt. Last year, he was a distant second in his debut on dirt at Saratoga and a decent fifth (beaten just two lengths) in the Remsen (gr. II) at Aqueduct. But it has been his recent dirt works at Palm Meadows that have encouraged the connections the most, and so for a chance at a $300,000 winner’s share and a trip back to Louisville, they figured—why not give him another chance?

“We can take him to Keeneland to run for $100,000 on turf or we can take him to Illinois for a shot at the Derby,” Repole said. “Where else am I going to run him? He’s been working great in company with Todd’s best 3-year-olds all winter. He’s worked with Windsurfer two works ago and El Padrino before that, and you couldn’t separate them. He’s also worked well with Discreet Dancer and Gemologist. Then on Sunday he breezed with Stay Thirsty and you couldn’t separate them either. They both went :47 and 4/5 and galloped out well. Granted, it was only the second four-furlong work for Stay Thirsty this year, but he’s also the Travers winner, so obviously Todd has enough confidence in Our Entourage to work him against good horses.

“I definitely think his better surface is turf, but he hasn’t raced on dirt since the Remsen, and he looks like a turf horse that can dirt. We saw what happened in some of these recent Derbies with Big Brown and Animal Kingdom (both raced on turf before winning the Kentucky Derby), so you never know. He’s matured as he’s gotten older and he’s going in there with five starts and a couple of two-turn wins, and no matter what happens he’ll gain some experience.”

With the Wood Memorial and Santa Anita Derby (both gr. I) being run on the same day, Repole locked up one of his favorite New York-based riders for the Illinois Derby—Eddie Castro. Castro’s instructions will likely be to put Our Entourage near the pace and give him a chance turning for home. With a pedigree that suggests he will enjoy longer distances, the 1 1/8-mile Illinois Derby might be right up his alley. And if not, Repole said it’s not the end of the world.

“I’ll compare it to the NCAA tournament,” Repole said. “He’s not a powerhouse from the Big East who already has his berth locked up. He’s from a mid-major and he needs to win his conference tournament to get in. This is his chance to get to the Big Dance. If he doesn’t take advantage we’ll probably send him back to turf.

“It would be nice to go back to Louisville for the Derby, especially with this horse who I named for the large entourage I take with me. Of course, my entourage is a little different than most; mine is with my 7-year-old niece and my 86-year-old grandmother, and all my family and friends, but it’s still an entourage.”

Repole said Overdriven, last year’s Sanford (gr. II) winner, is back in training and being pointed toward a May return. He also said Stay Thirsty is rounding into shape and is close to his return as well, perhaps the Westchester (gr. III) on April 28 at Belmont Park as a starting point.

The Illinois Derby is expected to attract a full field of 14. The top name so far is Currency Swap, who won last year’s Hopeful (gr. I) and was second to Gemologist in his season debut in an allowance race last month at Gulfstream. The field will be drawn Wednesday, April 4.