New York Islanders right wing Josh Bailey David Kirouac-USA TODAY Sports

Veteran Josh Bailey is a late entrant into the upcoming free agent market after the Blackhawks officially bought out the final year of his contract earlier on Friday, basically accepting a 2026 second-round pick from the Islanders to execute that move and carry the nearly $4M combined in dead cap charges over the next two years. However, that doesn’t mean that he won’t have suitors in free agency; Postmedia’s Bruce Garrioch reports that the Senators are linked to the winger.

The 33-year-old surpassed the 1,000 games played mark early this past season but things didn’t go particularly well for him. Bailey managed just eight goals and 17 assists in 64 games. By the end of the season, he was a frequent healthy scratch and didn’t suit up at all in their first-round loss to Carolina, basically cementing that he’d be on the way out at some point.

That said, Bailey is only a year removed from a 14-goal, 44-point campaign and would be an intriguing addition if a team believes that he’s capable of having a bounce-back season. With the year he had and the fact he’s receiving nearly $2.7M from Chicago, there’s a good chance that Bailey will be signing a relatively cheap deal, limiting the risk.  If he does indeed wind up in Ottawa, the hope would be that he’d add some offensive depth to a bottom-six group that struggled to produce at times in 2022-23.

There are some ties between Bailey and the Senators.  In his junior days, he played in Windsor for two seasons where Ottawa head coach D.J. Smith was a part of the staff. Meanwhile, current Sens associate coach Jack Capuano coached Bailey for parts of seven seasons with the Islanders so if Bailey chooses to go there, he’ll have plenty of familiarity with at least two of his new coaches.

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