Lucky Chappy will add to his gaudy number of frequent-flier miles when he starts in the Group 2, $2 million UAE Derby at 1 3/16 miles over the Tapeta surface at Meydan on March 31. An Irish-bred colt raced by the Animal Kingdom connections of Team Valor International and trainer Graham Motion, Lucky Chappy began his career in Italy, competed on both coasts in his four-race North American campaign, and, if all goes right in Dubai, will return to Churchill Downs on the first Saturday in May for a run in the Kentucky Derby. It’s an unconventional route, to be sure, but Team Valor took an out-of-the-box approach to last year’s Triple Crown series with Animal Kingdom, a colt that had never raced on dirt before the Derby. In fact, aside from a six-furlong breeze at Churchill Downs a week before his Derby win and several short workouts at Adena Springs prior to his career debut at 2, Animal Kingdom had virtually no experience over a dirt track. That didn’t stop him from upsetting the Derby at 20-1. Along with Lucky Chappy, Team Valor currently has three other Kentucky Derby aspirants in Howe Great, winner of the Grade 3 Palm Beach Stakes on grass at Gulfstream; State of Play, who took the John Battaglia Memorial over the Turfway Polytrack; and Gulfstream maiden winner Went the Day Well. Keeping the four sophomores separated while acquiring enough graded earnings necessary to earn starting berths in the Derby gate is challenging enough. When three of the four have shown a preference for turf and synthetic racing, the task becomes even more difficult. Howe Great may opt for the Grade 1 Blue Grass Stakes over the Keeneland Polytrack, while State of Play and Went the Day Well could head for the Grade 3 Vinery Racing Spiral Stakes at Turfway. While Lucky Chappy could certainly test the deeper waters in major dirt preps like the Arkansas Derby, Santa Anita Derby, and Wood Memorial, the UAE Derby offers a huge pot over a surface he adores. The competition might be weaker as well. If he handles the trip well, it looks like an excellent spot. Foaled in Ireland on April 5, 2009, Lucky Chappy sold for 16,000 euros at the SGA yearling auction in Italy. His sire, High Chaparral, won six Group 1 races on turf, including consecutive editions of the Breeders’ Cup Turf. High Chaparral was successful at the highest level of racing between seven furlongs and 1 1/2 miles and received a 112 Beyer Speed Figure for his dead-heat score in the final race of his career, the 2003 Breeders’ Cup Turf. At stud, High Chaparral’s Group 1-winning progeny include North American Grade 1 turf winners Wigmore Hall, Redwood, and Wrote. Lucky Chappy’s dam, the Distant Relative mare Germane, won the Group 3 Tattersalls Rockfel Stakes at seven furlongs on turf at Newmarket. Germane also has foaled Granted, a multiple stakes-placed filly on turf in France and Germany. This is the female family of Running Stag, who won three Grade 2 races going long on dirt in North America after being imported from Europe. Running Stag earned a 118 Beyer in winning the nine-furlong Brooklyn Handicap at Belmont. Lucky Chappy made his career debut May 25, 2011, in a seven-furlong maiden race on turf in Italy and finished second as the betting favorite. Three weeks later, he showed good speed en route to a facile four-length win at Capannelle. Lucky Chappy handily won his final Italian start, the listed Premio Giuseppe de Montel, by three lengths on July 3 and was purchased privately by Team Valor. Although Lucky Chappy was among the early leaders in his Italian races, he has had problems getting out of the gate in North America. In his stateside debut, the Grade 3 Bourbon Stakes at 1 1/16 miles on turf at Keeneland, Lucky Chappy broke last and was far behind the field heading into the clubhouse turn. Still last turning for home, Lucky Chappy raced in a bit of traffic in upper stretch before splitting rivals. He rallied well for third and finished ahead of two next-out winners.[bc_video_id:236247:] Lucky Chappy next raced in the Grade 1 Breeders’ Cup Juvenile Turf going a mile at Churchill Downs. Again, he was off a beat slowly and raced keenly passing under the Twin Spires for the first time. Lucky Chappy was three wide at the rear of the field on the first turn and continued the overland journey on the backstretch. Widest turning for home, Lucky Chappy was a bit late to make his final lead switch, but still finished well for fourth.[bc_video_id:237900:] Lucky Chappy missed some time with a fever prior to his 3-year-old debut in the $100,000 Kitten’s Joy Stakes at Gulfstream Park. Again, he broke slow, but soon found a nice spot in midpack. Lucky Chappy made a three-wide bid on the final turn, but couldn’t reel in pacesetting Howe Great. Shipped to Golden Gate Fields for the Grade 3 El Camino Real Derby over Tapeta, Lucky Chappy showed that he could handle the main track. Yet again, he broke poorly and was far behind down the backstretch. Heading into the final turn, Lucky Chappy made an eye-catching four-wide bid and was forced six deep at the quarter pole. He battled hard with the ground-saving Daddy Nose Best for the entire stretch drive, but just fell shy at the wire. Lucky Chappy received a career-best 93 Beyer for his performance in the El Camino Real.[bc_video_id:244635:] Lucky Chappy has some ability, but he must improve his break. If he doesn’t learn to get away from the stalls cleanly, he could be prone to traffic trouble in races featuring big fields. He is bred for turf and still needs to show that he can run effectively on dirt. Plus, if he does run well in Dubai, Lucky Chappy will have to overcome the rigors of international travel prior to the most demanding race of his life. Still, if anyone can get this horse to the Derby, it is Team Valor and Motion. If he earns enough cash in Dubai, it is likely that he will get his chance to shine in Kentucky. With his late-running style, a hot pace in the Derby could work to his advantage.