Bailey grew up in Clarington, Ontario, playing AAA for the Clarington Toros of the Ontario Minor Hockey Association\'s (OMHA) Eastern AAA League. He was drafted in the first round of the Ontario Hockey League (OHL) priority selection by the Owen Sound Attack in May 2005. He was traded by the Attack to the Windsor Spitfires during the 2006–07 season.\n', '

Bailey was selected ninth overall by the New York Islanders in the 2008 NHL Entry Draft. The Islanders\' General Manager Garth Snow traded down twice in the draft (from fifth to seventh, and seventh to ninth) to acquire Bailey. On October 2, 2008, his 19th birthday, the Islanders signed Bailey to a three-year, $900,000 contract. \n', '

Shortly after on October 7, 2008, the team announced that Bailey would begin the 2008–09 season with the team in the NHL, but his debut was delayed by an injury sustained during a preseason game. He scored his first goal in the league on January 2, 2009, against Ilya Bryzgalov of the Phoenix Coyotes.\n', '

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