I would lose all respect for him. Going for a paycheck instead of a winner.
The paycheck will come either way.
I don't think "losing respect" is fair (and I don't mean in a personal way because I don't think that's how you meant it) but let's say he's faced with these three options (of course there will be more), but to keep it simple:
1) re-sign with Isles for 8 yrs at 11 - 88mill
- meets with Scott Malkin, assures him ownership is committed to winning, will do what he can to spend to the cap (or close) and bring in whatever it takes - GM/coach/player dev/etc. (This is still the likeliest scenario)
2) NYR or MTL offer 7yrs at 14MM - 98mill
- no closer to winning in the short tem, BUT both orig six franchises will spend to the cap and do whatever it takes. He either stays in NY area and/or to a hockey hot-bed.
(This is "taking the money" and pricing himself above what his on-ice value is, kinda making it tough to build a winner in those markets BUT he's been underpaid for so long, maybe he just takes the money - sounds pretty appealing to me)
3) TAMPA or TOR offer 7yrs at 8mill - 56mill total (extreme example)
- clearly wants to win, will take less money and enjoy the next 3-4 years which essentially guarantee playoffs and wicked on-paper teams. Both can easily fit him under the cap because they are loaded with easily movable assets and can cut payroll EASILY. And Tampa is tax free so his take-home would be pretty good
(Another scenario, more about winning than pure greed)
Frankly, if it was me, I have no idea what I'd choose.
#FirstWorldHockeyProblems ?
I'm not saying that's what I want him to sign for, but I think he'll get at least McDavid money. I'd like to see him at 10.5-11.5. Barzal has another 2 years on his ELC. Snow/Snow's replacement can get rid of Clutterbuck and/or Ladd in that time to easily keep both Tavares and Barzal.
The Rangers, Canadians would easily pay more than McDavid. No question about it.
He'll get "way above market value" because he's a 27yr old superstar centre - and those two teams are desperate for a centre and cannot ever get one.
If you look at it a different way, how much is Tavares worth relative to McDavid, that's not the same. But that's also completely unrealistic because the situation is different. And once McDavid is a UFA, he'll likely get even more - just the way things go.