Craig started skating at the age of six, follwoing in the footsteps of his older sister. After he finished 11th at the 2004 Nationals, Craig didn't receive any international assignments. However, he felt he had improved a lot over the summer and sent a videotape of his programs to the Canadian Federation, asking for an international competition. The officials assigned him to the Nebelhorn Trophy in September 2004, and Craig won the event.