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Josh Bailey, Islanders Nearing Contract Extension?

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Something around 5-6 years at $5 million is close, says league insider Bob McKenzie

New York Rangers v New York Islanders
Making money, keeping it in the family.
Photo by Abbie Parr/Getty Images

This is not something I’d have ever expected to write before this season, but Josh Bailey and the New York Islanders are closing in on a contract extension that would average around $5 million per season for five or six seasons, according to longtime NHL insider Bob McKenzie. Brian Compton of NHL.com re-iterated that things are “close” but not official yet.

McKenzie speculated what we all have wondered: that assuming the sides close the deal, it would be a factor(?) in John Tavares’ deliberations over his own future.

Both forwards are linemates on the first line and are the two longest-serving current Islanders players. They are both on pace for career years — always a red flag when re-upping players to long-term deals that take them into their 30s, but so goes the league.

Bailey will turn 29 at the start of next season, so such a deal would take him through his age 33 or 34 seasons. Drafted as a center and thrust into the NHL right away on a bad team (so bad they were able to draft Tavares at first overall the next summer), he had an up-and-down adjustment and was converted to wing.

Throughout his career he’s been a decent middle-six winger and penalty killer usually scoring at about .5 points per game. But over the past 100 games he has hit a new groove as a point per game player (62 points in 57 games this season), finding chemistry and striking gold on the top line and power play, where he’s logged 28 of his 62 points. (His previous season-high point total was 56 last season, when he also recorded his previous season-high power play point total of 12.)

Bailey’s ascendance this year holds some dangers for the Islanders:

  • Have they finally found, along with Anders Lee, long-term solutions to wingmen for Tavares? They certainly are betting so.
  • Has that cost them by coming in Bailey’s walk year, when his leverage is at its highest? Yes.
  • And if part of this, and other pending moves, are designed to keep Tavares happy and comfortable...is it going to work?

The Islanders are accustomed to letting top-six scorers leave or depart in rental trades (P.A. Parenteau, Mark Streit, Matt Moulson, Kyle Okposo) once their market power got pricey. Sometimes those decisions have looked good in retrospect, particularly in the later years of the deals they signed with other clubs.

But the Islanders also have locked up bottom-of-the-lineup players to long-term deals and committed long and pricey to new players heading into their 30s (Johnny Boychuk, Andrew Ladd).

So it’s hard to infer there was too much financial consideration involved here, assuming this deal completes. Bailey wanted to stay and the Isles believe in him, so they are giving him nothing more (and probably less) than what he was likely to find on the open market as a guy producing at a point a game.

(And again, it doesn’t hurt if this truly does positively impact Tavares’ decision this summer.)

If they had let him walk and gambled on finding a “true first line winger” on the open market, they’d surely pay more — if one could be found and coaxed to choose them — with Mathew Barzal needing a contract extension just over two years from now and Jordan Eberle ($6 million cap hit) and Lee ($3.75 million) entering their walk years next season.

Clearly, they’ve decided Bailey is part of the long-term solution and the part of the team, offense, that isn’t broken. Tavares and coach Doug Weight have each spoken this season of their belief that Bailey finally put it all together, beginning midway through last season and continuing through this year and his first-ever All-Star Game appearance.

Lots of fans will pile on him, as they’ve done for years as a magnet for frustration about the management that has been in place for his entire 10-year tenure. This contract will only amplify that segment. But say this for him, he will keep on keeping on, toiling for the only NHL team he’s called home.

If he’s lucky, they’ll even fix the defensive half of the roster before his next UFA period arrives.