These questions are tough to answer because we're not GM Don Sweeney, but we can take a deeper dive into what he should do.
I saw this asked on Twitter earlier today, and it might be the biggest question revolving around the Boston Bruins' offseason:
@BruinsNetwork on Twitter hit the nail right on the head with this one as he wrote:
The Defense:
Trading a first-round pick for Hampus Lindholm and signing him to a max-term deal isn't necessarily a terrible move for Boston, as they now have a top pair of Lindholm and McAvoy who are both locked up till the end of the 2029-30 season. They're also in good shape with shutdown types in Brandon Carlo through 2026-27 and Derek Forbort through 2023-24.
If prospects like Jakub Zboril and Jack Ahcan make a strong enough case to be NHL ready, then I think Don Sweeney has to look at the possibility of moving one of Mike Reilly or Matthew Grzelcyk for cap relief, as the Bruins only have around $5,000,000 for next season right now.
The Forwards:
The biggest question on forward is captain Patrice Bergeron's future. If he doesn't retire, I genuinely believe he's returning to the Bruins and not going somewhere else. However, I think Boston still has to be aggressive in finding a top-six centre because Haula just isn't a number two centre, and Bergeron may be losing his number one centre status with age. A trade involving Jake Debrusk should still happen to try and fill that need down the middle.
The bottom six may actually be okay with Charlie Coyle, Erik Haula, Craig Smith, Trent Frederic and Tomas Nosek all still on the books. With younger guys like Marc McLaughlin and even Fabian Lysell or Georgi Merkulov with an opportunity to fight for a spot and give those older guys some competition.
The Goaltenders:
The Boston Bruins have a young and promising duo between the pipes with Linus Ullmark and Jeremy Swayman, who seem to have a great friendship and chemistry. Swayman should go into his second NHL season feeling really confident. He was in no way at fault for this year as a first-year goalie. He even got game seven experience against an excellent Carolina team and has a very bright future ahead of him. The only thing Sweeney should worry about with his goaltenders is signing Swayman to an extension.
Should Don Sweeney get aggressive this summer?
Injuries to key players may hinder the process but Sweeney does need to be aggressive.
If Bergeron retires, then Boston may slip into an area where they don't want to be mediocrity. The core in place without Bergy won't be good enough to make noise in the playoffs but not bad enough to be a bottom-feeding.
If Bergeron doesn't retire, Sweeney has to be aggressive to give him a contending team to try and win one last Stanley Cup.