I get why Boston doesn't want to give him that kind of money, he had a good playoffs but he hasn't ever played 60 games in a season, and you have no real track record to go on. Even 8 x 8 is a huge gamble under those conditions.
As for those that think Swayman has Boston over a barrel, he doesn't, and every day that ticks off towards December 1st he loses a little more of whatever leverage he does have.
For those saying he can go play in Europe, its not going to happen, because no one in Europe is going to pay him 5-6 million for the season, and if he has an agent that is trying to get every dime out of a team he is not going to let Swayman lose that kind of money. Any way you want to look at it that would be hard to scratch back even over a 10 year career.
So yeah Boston may hurt a little while until he signs, so what? Its better to have a little short terrm pain now than to be dealing with an overpaid goalie for the next 8 years.
Based on what he has proven so far I don't think any organization would be willing to fork out an 8 year deal anywhere close to 8 a season, let alone anywhere close to 10. Thing is teams usually will take gambles on contracts like this to save a bunch of money on the back end if they really believe in a guy, but at 9-10 million a season you aren't saving enough to be worth taking that gamble.