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In touch with the field through six furlongs, Itsmyluckyday tired to finish a disappointing 15th in the Kentucky Derby on May 4, the worst outing of his 11-race career.
Out of multiple Grade 1 winner and champion older horse Lawyer Ron, Itsmyluckyday had been off the board only twice previously, the final two races of his 2-year-old season, the latter on turf.
This year, he opened with a 6 ¾-length romp in the $100,000 Gulfstream Park Derby before decisively beating 2012 juvenile champion Shanghai Bobby by two lengths in the Grade 3 Holy Bull, his first race under jockey Elvis Trujillo.
Following a two-month break, Itsmyluckyday was favored to win the Grade 1 Florida Derby, finishing a strong and decisive second behind eventual Kentucky Derby champion Orb.
Itsmyluckyday began his career sprinting at Monmouth Park before heading to Florida, where he won an off-the-turf sprint in the slop and stretched out to a 1-mile, 70-yard victory over a fast track in successive starts, both at Calder Race Course.

