Career
Bailey played junior A hockey for the Alberni Valley Bulldogs of the BCHL from 2009-2012 before going to play college hockey with the Penn State Nittany Lions. Having not been selected in any National Hockey League Entry Drafts, Bailey signed a two-year, entry-level contract with the Toronto Maple Leafs on March 21, 2015. He became the first Penn State player to sign an National Hockey League contract, as well as the first to play in the National Hockey League. Bailey was coming off a sensational 2014-2015 junior season in which he finished fourth in scoring within the Big Ten Conference when he signed with the Leafs.
According to Damien Cox of Sportsnet, 14 other National Hockey League teams also had gained interest in Bailey.
He adds that Bailey had previously attended training camps with the Boston Bruins and Calgary Flames. Prior to signing, Bailey was near completion on an entry-level deal with the Buffalo Sabres, however, the Sabres were unwilling to meet Bailey"s demands of playing in the final few games of the team"s season, prompting the signing with Toronto.
Bailey scored his first National Hockey League goal in the last game of his inaugural season, on April 11, 2015, against Carey Price of the Montreal Canadiens. During his first full professional season in 2015-2016, Bailey was re-assigned to AHL affiliate, the Toronto Marlies, and produced 18 points in 38 contests before he was included alongside Dion Phaneuf in a 9-player trade to the Ottawa Senators organization on February 9, 2016.
