NY Islanders: Lamoriello has 'difficult' conversation with Bailey after trade

As apparent it was that the relationship between the New York Islanders and Josh Bailey would come to an end this summer, it was also clear that GM Lou Lamoriello ideally wanted to work out a scenario that was both best for the player and the team if possible.

"Loyalty will never get in the way of impeding progress. We will work with him to help him," said Lamoriello earlier this month. "My priority is doing what's best for the team."

Before the second round of the 2023 NHL Draft began, it appeared Lamoriello had done just that, trading Bailey along with a 2026 second-round pick to the Chicago Blackhawks, unloading the veteran winger's $5M AAV for the salary cap-crunched team.

Soon after fans looked at the home schedule to see when the Blackhawks, first-overall pick Connor Bedard and Bailey would be visiting UBS Arena, it was reported that Chicago was placing him on unconditional waivers for the purpose of a buy-out. Blackhawks GM Kyle Davidson told the media that there wasn't a "logical place on the roster" for Bailey, so buying him out made the most sense for the rebuilding franchise.

It is unclear whether Lamoriello and the Islanders were aware of the Blackhawks' intentions when they made the trade. While meeting with the media, the Isles GM said he had a 'difficult' conversation with the previously longest-tenured Islander this morning, notifying him that he is no longer with the only team he's ever known.

"I came here as a teenager and got married. All our kids are born here, and all the roots are here, and this is where we plan on living when hockey is all said and done, said Bailey back on May 1st about his time on Long Island. "Fifteen years has been a pretty good run, and I'm very proud of that."

Bailey is reportedly on a golf trip in Europe with some of his teammates, demonstrating again how close this group has been on and off the ice. While there isn't an NHL rule preventing the Isles from bringing back Bailey on a veteran minimum contract after he clears waivers and is bought out, such a move is very unlikely.

Bailey reached the 1,000 games played milestone last season, scoring eight goals and 17 assists in 64 games while averaging just 15:08 TOI, the lowest in his career. Despite diminished stats and playing time, he's stated he still feels he can play at a high level and help teams win.

After a day where he was traded, waived, and bought out, he'll be a free agent for the first time in his career. Bailey now has options and an opportunity to find the best situation for him around the league. "I don’t think it could have worked out any better under the set of circumstances, fortunately, said Lamoriello on Thursday afternoon. " I’m delighted that it worked out this way so that he can get an opportunity where he’d like to go.”