This run ... the Bruins have been fun to watch for the last 15 years. This core - Bergeron, Marchand post-2010, Krejci, Lucic for half of it, McAvoy/Pasta for the other half, Chara for most, Rask, Thomas for the first part, Krug in the middle - was just incredible to watch. The Bruins had an identity, retooled, and maintained their status as one of the league's elite teams for 15 years, which is unheard-of in the cap era.
They've left a lot wanting, though. 3 Cup Finals, a President's Trophy and one Stanley Cup in that run ... 2019 will always sting because that was there for the taking, but the two that hurt most next to it were 2012 (when they lost Game 7 in OT at home to a mediocre Washington team and the bracket *completely* broke open after that ... they'd have played the Devils in the second round and I'd have liked their chances against the Rangers/Flyers & Kings) and 2014 (when they were an absolute wagon, but Dennis Seidenberg went out for the year in February and their D was decimated by the playoffs). They hit about 157 posts against Carey Price and every single Montreal scoring chance ended up in the net. Again, you like their chances against the Rangers & Kings in the last two rounds, even with a young and decimated D corps.
2020, there's a whole what-if if the world doesn't come to an end. The Lightning were dealing with injuries, the Bruins were flying ... and after the pause, the B's never really seemed to get their mojo back, Tampa healed up and then Tuukka had to take care of a family emergency. The B's weren't beating the Lightning and a dialed-in Vasilevskiy with Halak in goal. 2021 - that series turned when Carlo got hurt and again, Tuukka was playing hurt (and in hindsight, should've given way to Swayman because of it).
It's the best sustained Bruins era of my lifetime ... the 1988-92 run was fun, with two Cup Finals. Again, they should've won in 1990 (when they were a better team than Edmonton but never recovered from the 3OT loss) and probably 1991 (when they went up 2-0 on Pittsburgh, but then Ulf Samuelsson's cheap shot on Neely and Milbury overreacting by dressing all of his tough guys the next game flipped the series and a Penguins team they should've beaten went on to beat Minnesota for the Cup. That window slammed shut with "May Day" and the scapegoat trade of Andy Moog that summer and the B's were largely a nonfactor for the next decade and a half (1994 felt like this year - yes, unlike this year, they won a playoff round and won two games against NJ, but they never really felt like a team that could challenge for a Cup).