Given he can say no to 15 teams, and Boston can't afford to retain, if Ullmark wants to stay in Boston, you're going to have a difficult time moving him, because he can say every team that needs a goalie AND has the cap space is on his list.

Why can't Boston afford to retain? Otherwise, I agree with what you are saying. He and his agent can make it very hard to trade him for a worthwhile return.

Also, I think he'd potentially be willing to waive if a team offered him a good contract in order to do so, but that would be risky for that team to do. Sounds like something that would typically happen at the TDL, but it is still possible in the offseason.

Because you're not going to sign a 1C for 3 mil as a UFA.

But let's dig deeper into this, what teams need a goalie and can afford to spend 5 mil on the position? LA was already declined, Minnesota can't afford it, Buffalo probably can but would Ullmark go back? Ottawa needs one but probably can't take the cap without sending one back, Edmonton's goaltending is feast or famine but they'd need to move Campbell. Philly needs a good goalie and should be able to afford him, Colorado can't afford him and just resigned their backup, New Jersey is looking but affordability is questionable, if Andersson is done then Carolina could use a goalie, Chicago and San Jose don't care about winning right now, Toronto can't afford the cap hit, maybe Arizona, Columbus and Detroit are both looking but need to unload their similarly priced goalies to do so.

NYR, NYI, FLA, TB, ANA, SEA, CGY, WPG, VGK, DAL, STL, NSH, WSH, all don't need a goalie.

So who's the match?

You gave a long-winded answer to the part I agreed with and a short flippant answer to my actual question. I personally think that the Bruins can retain up to half for a year and still sign 2 guys in their top 6 and one in the top 4 on the backend as long as they are not targeting the top UFAs at those positions. Not each of those needs to be premium players, but they do need to be able to play the part at least. If they target one positional top UFA like Hanafin, then maybe they can't get one of those slots filled, but so be it. While they would love to get back into contention, they need draft picks if they ever want to get a true 1C, so another bridge year could be worth it.

There is no true 1C available as a UFA this offseason, and they should sign players based on their long-term value to the team (probably a 2C). No need to overpay someone, so you don't need to earmark part of their cap space for a $9m+ player. They should continue to maintain their flexibility while in the re-tool.

The cap is going up for the first time in years, guys are going to be out there looking for a payday as UFAs. I doubt you'll be able to get a 3C capable guy for 3 million. Middle 6 guys have been getting 4-5 mil AAV, I would add ~10% bump to previous salary comps from the past two years.

You might get some guys who are well into the back 9 of their careers to sign cheap, but I don't believe anyone who's capable of top 6 play is going to come to Boston on a discount.

You did find an issue with my argument -- I said top 6 guys, but what I should have said was middle 6 guys who can play well on the 2nd line or aging top 6 guys. I am not sure why you keep saying $3m, but I have always assumed that their 3 main holes would cost on average about $5.5m to fill. I am thinking that guys like DeBrusk, Stephenson, Toffoli, etc can be had in the $5-6.5m range. On LD, there are also some impact guys potentially available who will be between 1-3m cheaper than Hanafin like Skjei and Dillon. I'd be totally fine with signing something like DeBrusk, Toffoli, and Dillon (or something similar). Throw in Swayman's raise, and we are talking about ~20m in cap space even with Ullmark on the team, which is pretty much what they have. I also wouldn't be upset if they brought in Hanafin and opted to sign a single top 6 forward and had someone play above their paygrade for a year, although I doubt that is how things play out.

They would still need to re-sign Boqvist (~1m I'd guess), but that is about it. If they traded Ullmark in this scenario and retained half or took back a 2.5m contract, they would still have enough to do that and sign or call up a 1.5m backup. Obviously this is all back-of-the-napkin, but hopefully I'm making it clear that retention (or a returning contract) are not necessarily the big hurdles this offseason. It is mostly just the no-trade list.

Why on earth would he do that? It will likely be the exact opposite of the advice his agent will give.

He can leverage a no trade clause for an extension. He covets stability. I understand why he didn’t want to leave his family during the offseason, but he isn’t getting an extension in Boston and locking into his next stop probably has appeal.

Boston can easily afford to keep him in 2024 if they can’t get the return necessary. Boston could easily afford to retain next year, but they will need to be compensated for it.