2009-10: Justin Bailey played for the Amherst Knights U14 team that reached the USA National Championships after attending USA Hockey's Select 14 Development Camp the previous summer. Bailey is the son of former Buffalo Bills linebacker, Carlton Bailey.
2010-11: Bailey skated in 12 games for the Buffalo Regals U16 team – missing much of the season due to a shoulder injury. He scored 4 goals with 1 assist for the Regals. Bailey was selected by the Indiana Ice in the first round (11th overall) of the USHL Entry Draft and by Kingston in the seventh round (128th overall) of the OHL Priority Draft.
2011-12: Bailey joined the the Pat Lafontaine-coached Long Island Royals midget team in the Atlantic Youth Hockey League and played two USHL games with Indiana. He had 1 goal in two games with the Ice. In 22 games for the Royals he scored 21 goals with 13 assists and had 52 penalty minutes. Bailey played in the 2012 USA Hockey Select 17 Festival in July 2012. He committed to playing college hockey at Michigan State in January but signed a contract to play for Kitchener in July.
2012-13: Bailey played for the USA in the 2012 U18 Ivan Hlinka Memorial tournament before joining the Kitchener Rangers for his first OHL season. In 57 games for the Rangers he scored 17 goals with 19 assists and was plus-22 with 34 penalty minutes. Kitchener finished third in the Midwest Division and reached the second round in the playoffs; falling to eventual OHL champion London. Bailey scored 1 goal with 2 assists and was minus-two with 4 penalty minutes in 10 playoff games. He scored two goals, including the USA's first goal of the tournament in a 2-1 shootout loss to Russia, in four games at the Ivan Hlinka Tournament. Bailey was ranked 38th amongst North American skaters in Central Scouting's final rankings prior to the 2013 NHL Draft.
Bailey has the potential to be a power forward in the NHL. He possesses good size at 6’3 and his playing weight is expected to be well over 200 pounds. He is difficult to contain coming out of the corners and though he is not particularly fast, he has a strong stride and difficult to stop at top speed. Bailey is an adept finisher around the net but finds it difficult to put everything together and play consistently every night.
Bailey is considered a project, having played less hockey than most of his peers. He is expected to play out his junior career and spend a few seasons in the AHL before becoming a regular NHL player.