Reagan began skating with Ashley Cain in April 2009. They were coached by David Kirby (son of Michael Kirby) and Peter Cain at the Dr. Pepper Star Center in Euless, Texas. Cain and Reagan finished 4th at the 2011 World Junior Championships and won the 2011 U.S. Junior title. On February 24, 2012, they announced the end of their partnership.