Mike Smith, a 59-year-old jockey, is set to compete in his record 29th Kentucky Derby, where he was 17 when he rode in the Kentucky Derby for the first time in 1984. Smith will be riding So Happy, the winner of the Santa Anita Derby for trainer Mark Glatt. If Smith wins, he would be the oldest jockey ever to win the Run for the Roses, currently held by Bill Shoemaker at 54. Smith, who has won the Derby twice and seven Triple Crown races, said he's dreamed his whole professional career he'd win three. He has been riding most of his life, starting at age 11 at the bush tracks in his native New Mexico.