Spending his entire career on Long Island is something the 36-year-old takes pride in. He knows how special it is to wear just one sweater throughout an NHL career and is proud to have done it with the Islanders.
"It was one of the greatest honors of my life to put on that jersey and play my entire career here in front of this fan base," Bailey said. "As a kid growing up in Ontario, I didn't know much about Long Island or the history of the team when I got drafted. I've lived here longer than anywhere else in my life, and it really feels like home."
Bailey was selected to the 2018 NHL All-Star Game during a season in which he recorded a career-high 71 points (18G, 53A) in 76 games.
Bailey elevated his game when it mattered most with 50 points (16G, 34A) in 71 playoff games. He was a key member of the Islanders runs to the third round of the playoffs in 2020 and 2021 and led the team with 20 points (2G, 18A) in 18 games in the 2020 playoffs.
Bailey scored two playoff overtime goals, including the Game 1 winner in the 2019 Eastern Conference First Round against the Pittsburgh Penguins, burying a rebound on a play forever linked with Brendan Burke's "Game 1, to the Island" call.
Bailey remains a familiar face to Islanders fans. He joined the Islanders Radio broadcasts before the 2025-26 season as an analyst.
"It was never something on my radar," Bailey said. "I love watching the game and analyzing it. Alan [Fuehring], Cal [Clutterbuck] and Hicks [Thomas Hickey] do such a great job, so they made my job very easy coming in."
He has remained on Long Island since retiring and is grateful for the support he has received from both the Islanders organization and its fan base.
"My family and I love it here, and it's become our home," Bailey said. "It's got the perfect mix of everything. You put all those factors together, and it's just a fantastic place. I'm proud to have played here for so long."