In winning a mile allowance at Gulfstream Park, he set a new track record of 1:34, slicing a second off the old record. His win in the Grade II Coolmore Lexington Stakes at Keeneland punched his ticket for the 2006 Kentucky Derby. Tagg said of the Derby, "They're only a 3-year-old once. I decided to make the switch to the grass because I thought Barbaro would win the Triple Crown. I can't imagine he'd have beaten Barbaro who went into the Preakness undefeated in six races. I thought Showing Up might have a chance to be the national champion turf horse." He added, "He did beat 14 horses in that race. He's no slouch."