1000+ game NHL veteran may be forced to consider retirement after failing to secure new contract

Bailey had a good preseason, scoring 6 points (1 goals, 5 assists) in six games, so his release comes as a surprise. There is still a chance another NHL team may sign him, but it seems doubtful.

Bailey was selected 9th overall in 2008 by the New York Islanders. They remain the only NHL team he's suited up for. Following a sharp decline over the last few years, he was traded to the Chicago Blackhawks this summer offseason, packaged with a 2nd round pick in 2026, for future considerations. It was a pure cap dump, with the Blackhawks immediately putting Bailey on waivers to buyout his deal.

In February of 2018, Bailey was signed to a new six-year contract with the Islanders that carried a $5 million per season cap hit. Former Isles GM Garth Snow negotiated the deal, and it serves as a good example of why he's no longer with the organization.