[2] At three, Caracortado won the 2010 Robert B. Lewis Stakes (G2), establishing himself as among the better three-year-old colts in North America when he drew off to a 1+3⁄4 length score over highly regarded sophomores Dave In Dixie, American Lion, and Tiz Chrome.
Following a six-month freshening after the Preakness, Caracortado returned under new rider Joe Talamo with a win in his turf debut in a November 11 optional claiming race at Hollywood Park, defeating older rivals in near-record time.
Entered in the December 26 Malibu Stakes (G1) on dirt at Santa Anita Park, he finished third to track record-setter Twirling Candy and Smiling Tiger.
On January 29, 2011, he returned to grass as a newly turned four-year-old in the Sunshine Millions Turf with a win in fast time over older graded stakes winners The Usual Q.T., Presious Passion, and Jeranimo.
He skipped an international campaign through the spring and focused on top North American grass races leading up to the November Breeders Cup at Churchill Downs.