2009-10: Vail played for the USHL's Waterloo Black Hawks as a 15-year-old after three seasons in the Detroit Compuware youth program. In 48 games he scored 4 goals with 4 assists and was minus-14 with 40 penalty minutes. Waterloo finished fourth in the East Division and lost to eventual USHL champ Green Bay in the first round. Vail played in 2 of 3 games in the playoff series and was scoreless and minus-two. Vail was selected by Windsor in the fourth round (67th overall) of the 2010 OHL Priority Draft.
2010-11: Vail skated in 61 of 68 games for Windsor in his first OHL season. He scored 3 goals with 7 assists and was minus-three with 27 penalty minutes. The Spitfires advanced to the third round of the playoffs after finishing second in the OHL's West Division. Vail scored 4 goals and was minus-2 with 4 penalty minutes in 16 playoff games.
2011-12: Vail was the third-leading scorer on a young Windsor team that finished under .500 for the first time since 2006-07. He scored 22 goals with 30 assists and was plus-one with 55 penalty minutes; skating in all 68 regular season games for the Spitfires. After finishing fourth in the West, Windsor was swept by Memorial Cup-bound London in the first round of the OHL playoffs. Vail was scoreless and minus-three with 4 penalty minutes in four playoff games. Vail was invited to the NHL Draft Combine and was ranked 38th amongst North American skaters in Central Scouting's final rankings prior to the 2012 NHL Draft.
Vail looks to be a two-way center with a bit of offense to his game. But his main stock in trade is his defensive play mixed with good hockey intelligence that makes him an effective checking forward. It remains to be seen if Vail will develop the offensive side of his game at the pro level, but he should be able to get a foothold based on his defensive play.
Vail needs to work on his overall offensive skills as well as developing a better shot and quicker release. He will probably continue his development in the OHL with the Spitfires over the next two seasons.