Education
He played Commonwealth of Independent States football at Saint Francis Xavier University and attended Our Lady of Mount Carmel Secondary School in Mississauga, Ontario.
He played Commonwealth of Independent States football at Saint Francis Xavier University and attended Our Lady of Mount Carmel Secondary School in Mississauga, Ontario.
He was drafted by the Edmonton Eskimos with the sixth overall pick of the 2014 Canadian Football League Draft. Bailey played for the Saint Francis Xavier X-Men from 2010 to 2013. He recorded 87 receptions for 1,160 yards and six touchdowns in his career.
Edmonton Eskimos
Bailey was drafted by the Edmonton Eskimos in the first round of the 2014 Canadian Football League Draft.
He was ranked Number. 5 in the final Canadian Football League Scouting Bureau rankings in April 2014. He signed with the Eskimos on May 31, 2014.
In his rookie season with the Eskimos, Bailey recorded 17 catches for a total of 219 yards. He recorded his first Canadian Football League touchdown on August 21, 2015 against the Hamilton Tiger Cats.