What the Islanders are betting is that Bailey's best years are still ahead of him. Or that at the least he keeps up the approximately .5 point per game pace he's had over the last 80 or so games (since he has been playing on the wing and looks like a totally different player).
Is it a risky deal? At face value.The Islanders have just made Bailey the second highest paid player on the team based on cap hit, depending on how his contract scales (we don't know if the cost of each season varies). That just sounds weird; Josh Bailey as #2 on the payment chart. But part of that is because Matt Moulson is entering a contract year and will surely be looking for more money on average in his next contract than the one he currently has (Moulson has a salary of $3.9M this year, but his average value is $3.13). And part of it is because the Islanders have locked up players at below market value. *cough* John Tavares' contract *cough*. Bailey was signed right at, or slightly above, fair market value.
Bailey's deal might sound weird; five-years and more than $3 million for a guy who, only just recently, is showing that he can contribute regularly.But it's pretty close to the going rate for players of Bailey's ability.
A few weeks ago, the Blue Jackets signed Artem Anisimov to a three-year deal. Anisimov is about five months older than Bailey and was also a RFA this summer. He had 18 points in 35 games this past season and has 126 in 279 career games. Compare those to Bailey notching 19 in 38 and 139 in 329. Anisimov's deal is for $3.28 per year and, if you didn't know who they were talking about, the "eh he's good but $3 million is a lot" vibe on the Hockey's Future CBJ board is sure similar to the complaints people may have about Bailey's deal.
Another comparable is Clark MacArthur of the Senators. At 28, MacArthur just got a two-year deal worth $3.2 million per. He's hit the 20-goal mark twice in his career, something Bailey hasn't done, but MacArthur was 20 in 40 this year for Toronto and is right around .5ppg for his career.
If Bailey's deal sounds weird, that's because what you think $3 million buys in today's NHL is a bit off. It's what players of his ability, or slightly better, are making these days. Of course we have to assume he'll keep up the pace he's been playing at over the last season and a half. With Bailey at only 24 years of age, that's not a bad bet to take. And if Bailey improves and players better than that, he'll be a steal in a couple years.