Ryan has been following Indianapolis baseball for most of his life, and the Pirates since they became the affiliate in 2005. He began writing for Pirates Prospects in 2013, in a stint that ran through 2016 (with no service time manipulation played in). Ryan rejoined the team in 2022, covering Indianapolis once again. He has covered the Pirates in four different big league stadiums. Ryan was also fortunate enough to cover the 2015 Futures Game in Cincinnati.