Bailey is 23-years old, a restricted free agent and coming off of a 19-point season in 38 games. He likely sees himself as part of the 'core' of the Islanders that have all been homegrown players who have been given multi-year deals (see: Tavares, Moulson, Okposo, Grabner, and most recently Hamonic). Whether it's the length or the value of the contract that's the hold up, we don't know, but my hunch is that Bailey may be looking for his own multi-year deal.
While the shortened season skews numbers, Bailey was on a career high pace for points over a full 82 games. Of course the other side to that coin is, could he have kept up that pace over a full 82?
He stepped up his game this year and looked like a much better player on the wing having moved over from center, but there is still the lingering question as to whether he can become an offensive threat in the league. With prospects like Brock Nelson and Ryan Strome expected to make a push in training camp plus Cal Clutterbuck's four-year deal, Bailey's spot, in the long-term at least, could be somewhat of a question mark.
We'll see how this plays out in the next month or so. Arbitration hearings usually take place in late July/early August.