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 played parts of two seasons with the Attack, scoring eighteen goals and adding thirty four assists. He was traded by the Attack to the Windsor Spitfires during the 2006–07 season. He played two seasons with the Spitfires.[1] In the 2007–08 season, Bailey registered 29 goals and 96 points in 67 games.[2]
Professional
Bailey during his first season in the NHL, December 2008
Bailey was selected ninth overall by the New York Islanders of the National Hockey League (NHL) in the 2008 NHL entry draft. The Islanders traded down twice in the draft (from fifth to seventh, and seventh to ninth) to acquire Bailey.[3] On October 2, 2008, his 19th birthday, the Islanders signed Bailey to a three-year, $900,000 contract.[4] Bailey made his NHL debut in the 2008–09 season.[5] Bailey made the team out of training camp.[6] He scored his first goal in the league on January 2, 2009, against Ilya Bryzgalov of the Phoenix Coyotes.[7] Bailey finished the season with 25 points in 68 games.[6] The following season Bailey started slowly but finished strong, registering 35 points in 73 games.[6] However, at the end of the season Bailey suffered facial fractures after being boarded by Alexei Ponikarovsky of the Pittsburgh Penguins. Bailey would miss the final two games of the season and Ponikarovsky was suspended for two games.[8]
After a better start to the 2010–11 season,[6] he was injured with a hip pointer, missing two games.[9] Upon returning, he had no points in a 13-game stretch, prompting the Islanders to send Bailey to their American Hockey League (AHL) affiliate, the Bridgeport Sound Tigers, in late November. Bailey had played 159 games in the NHL to that point,[10] one game before Bailey would have had to clear waivers to be sent down to the AHL, which starts at 160 NHL games. Bailey played 11 games in the AHL and scored six goals and 11 assists before being brought back up to play with the Islanders again in December.[6] At this point in his career, Bailey was cited as an example of part of the nadir of the Islanders franchise.[11] Bailey finished the season with the Islanders, registering 22 points in 52 games.[6] On September 15, 2011, he signed a two-year contract with the Islanders.[12]
With the 2012–13 NHL lockout in effect, Bailey was signed to a temporary lockout contract with German second division club SC Bietigheim Steelers on November 9, 2012.[13] Bailey accumulated 11 points in six games with the Steelers before returning to North America. The Islanders announced on January 15, 2013, that they had suspended Bailey due to sustaining an injury while playing for the Steelers, and that he would not collect any pay from the team during the suspension.[14] After the lockout ended, Bailey returned to the Islanders scoring 11 goals and 19 points in 38 games.[15]
Bailey signed a five-year, $16.5 million contract with the Islanders on July 15, 2013.[15][16] He finished the 2016–17 season with new career highs in goals (13) and points (56).[17] During the 2017–18 season, Bailey scored his first career hat trick in a 6–4 loss to the Columbus Blue Jackets on December 14, 2017.[18][19] Posting 18 goals and 53 assists for a career high 71 points, he was selected to his first NHL All-Star Game on January 10, 2018.[20] On February 23, 2018, Bailey agreed to a six-year contract extension with the Islanders.[21]
Bailey with the Islanders in December 2017
Bailey was named an alternate captain ahead of the 2018–19 season.[22] On April 10, 2019, Bailey scored his first playoff NHL overtime winner against the Pittsburgh Penguins.[23] He scored his second overtime winner on May 24, 2021, again against the Penguins, on a turnover from Pittsburgh goaltender Tristan Jarry.[24]
On October 28, 2022, Bailey played his 1,000th NHL game against the Carolina Hurricanes and became only the third player from the Islanders to play all 1,000 games with the team.[25] At this point, the view of Bailey as a player had improved among fans, though still "polarizing" to many.[2] Bailey finished the 2022–23 season with eight goals and 25 points, his lowest total since his rookie season.[26]
In the off-season, on June 29, 2023, Bailey was traded to the Chicago Blackhawks along with a 2026 second-round draft pick for future considerations as the Islanders intended to dump his contract on a team with more space under the salary cap.[26] The Blackhawks immediately placed him on unconditional waivers with the intent of buying out his contract.[27] Approximately two months later, on September 14, Bailey was signed to a professional tryout (PTO) agreement with the Ottawa Senators.[28] He was released by the Senators from his PTO on October 8.[29]
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