Josh Bailey Bob Frid-USA TODAY Sports

Often overlooked among a given year’s unrestricted free-agent class are the late additions — unqualified restricted free agents and bought-out players. Longtime New York Islander Josh Bailey falls into the latter category. Unlike other prominent bought-out names, such as Matt Duchene and Oliver Ekman-Larsson, he remains unsigned as we enter August.

Bailey was one of the more underrated franchise cornerstones in the league for quite a while. Never really viewed as a high-end piece, Bailey didn’t let that stop him from being one of the more consistent Islanders forwards throughout the 2010s. A gifted playmaker, Bailey was money in the bank for between 40 and 60 points and played well enough, no matter who you put him with. He’d begun to drop off after his 30th birthday like so many others, however, leading the Islanders to deal him to the Chicago Blackhawks, along with a 2026 second-round pick, for future considerations last month. Chicago promptly bought him out, making Bailey an UFA for the first time in his 15-year NHL career.

It’s been all quiet on the western front for Bailey as of late. However, reports immediately after Chicago bought out Bailey suggested the Ottawa Senators were circling the veteran winger. It’s a fit that makes a fair bit of sense for both sides given Ottawa’s lack of scoring depth, especially on the fourth line.

His built-in versatility makes him an attractive option for a bottom-six role as he ages, and he’s still a valuable playmaker and penalty-killer in isolation. His declining speed and skating limit him from being effective in a top-six role, but there are far worse veteran additions to plug-and-play this late into the offseason.

Stats

2022-23: 64 GP, 8-17-25, +3 rating, 2 PIMs, 72 shots, 48.2% CF, 15:08 ATOI
Career: 1057 GP, 184-396-580, -48 rating, 241 PIMs, 1591 shots, 48.1% CF, 16:32 ATOI

Potential Suitors

Any team with any cap space to spare could likely fit Bailey in. He’s unlikely to command over $1M on a one-year deal and is ineligible for performance bonuses. While he’s unlikely to take a role with a team already filled out on the wings, quite a few teams could use Bailey as an upgrade on their bottom two lines.

As mentioned earlier, Ottawa is quite a clear fit in the Eastern Conference. The Sens have over $5M in cap space to spare, per CapFriendly. While they still have Shane Pinto to re-sign, he won’t command all of it. Bailey is a significant upgrade over the team’s currently projected fourth-line wingers, Parker Kelly and Egor Sokolov, and he could help catalyze some offense from the team’s third and fourth lines. The Sens could use it after taking a goal-scoring hit in their top six by swapping Alex DeBrincat for Dominik Kubalik.

He could also head out to a team with a winning pedigree, the Colorado Avalanche. After a flurry of offseason additions, including Ross Colton and Ryan Johansen, the team still has a handful of depth forward spots available for competition. Bailey’s a more experienced option than Fredrik Olofsson, whom Colorado acquired from the Dallas Stars in exchange for future considerations earlier this summer and promptly extended on a league-minimum contract. If nothing else, he’d give Avalanche head coach Jared Bednar more options to organize his second, third and fourth lines. There are many question marks regarding how the Avs’ opening night lineup card will look in any event.

Projected Contract

Bailey did not appear in our top 50 UFA rankings list, nor was he eligible thanks to his buyout. There’s no feasible way his next deal lands anywhere close to his previous $5M cap hit or even his $3.5M salary that he was due for 2023-24, especially at this point in the summer. However, a handful of playoff-hopeful or contending teams (as outlined above) could afford the veteran on a deal worth $1M or less. Given his declining role and production, he’s likely to receive a number in that range from any team that approaches him, regardless of contention status.

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