In management's defense, both times they were offering the cap room they had available. Read somewhere that before arbritration, they offered him something in the mid $3 range, he wanted something in the $4 range. I guess management knew how arbitration works and Gross didn't. I believe they low-balled and took the 1 year option as they knew the result would be in the $3's based on past experience. Gross should've realized that arbitration wouldn't get them $4+ and that the team would make him sound more average that he is. That's the way the game is played. A team can only spend what it has available to spend without either trading away an asset or not playing with a full roster. He also hadn't really proven himself at that point, their offer in the $3's for one year wasn't an insult IMO.
This time, the Bruins kept $8-$8.5 in cap room with a full roster. This time, they didn't choose the arbitration option to try to keep his salary down. According to Cam's statement, they are pretty much offering him the room they have, keeping a little bit to have some flexibility. It's certainly not a low-ball offer, very fair IMO based on his current resume. People can say that cap room isn't a player's problem, but it's a factor in the real world.
Shane Pinto faced a similar situation last year, well worse because our dumb GM at the time, Dorion, didn't have any cap room to sign him above league minimum. Then he was suspended for half the season and ended up taking the league minimum deal for the rest of the season as that was the cap space new owner/GM had to work with. His bridge contract this past summer was for 2 years, with the 2nd year paying him $5 million which means his next QO has to start with a 5 if I understand the process correctly. I think Pinto knew the pickle they were in and worked with management to come up with a viable solution. Ironically, Gross is also his agent but it is the player that has control so I guess Pinto must've been involved with the negotiations. I think he also appreciated that the Sens management team supported him throughout that ordeal.
If Swayman doesn't want a long-term deal under $70 million, then he should negotiate a bridge deal for 4 years and get his big pay day when he's a UFA. I know there are 2 comparables for the $9 million deal for an RFA goalie, but not all GMs are willing to pay top dollar for an RFA goalie with a small sample size. It doesn't make them bad GMs if the # they do offer is fair. He wants the big payday now and have the Bruins take on all of the risk if his performance declines or he gets injured a lot, and his contract becomes an albatross. Not likely to happen, but it can happen, especially with goalies. This stalemate isn't all on management IMO.