Here's one that I'm surprised wasn't on here. The 2010s Boston Bruins. Now I know they won in 2011, but made it back in 2013 after beating Toronto in game 7 they ran over the Rangers and Penguins and were the better team vs the Hawks. Remember in game 1 they had a 3-1 lead in the 3rd that they blew, and had a chance to go back to Chicago up 3-1 in game 4 but lost in ot after coming back to tie the game 3 times. In 2014 they ran over evreyone and were the odds on favorites heading into the playoffs after beating Detroit easily in round 1, the wheels fell off after blowing a 3-2 series lead and a series that could have ended in 5. And last year in 2019 after the big favorites in Tampa went down early it was the Bruins to lose. After losing game 5 on a controversial call, they won game 6 only to lose the cup on home ice on game 7.
It's hard to pick which year i want to go with.
2009, 2012, 2013, 2014, or 2019.
2009 might've been my favorite team in some respects- the franchise was dead in the water for a long time, and they grew from the ruins of the Thornton trade into a 1-seed. And they don't even get beat by another contender like Pittsburgh, Washington, or Detroit. They get knocked out by frigging Carolina. That really sucked and was really hard to take after such a fun season.
2012 was another fun year. They had like a 14 game winning streak at some point and were on fire, but injuries to Horton kinda slowed them down, and they drew a really bad match-up with Washington in the first round and got bounced in OT again.
2013 was a really fun ride with a crappy ending, but I'm at peace with losing to the Blackhawks because I do think they were a better team. Still, if Daugavins doesn't f*** up the empty net in triple OT, who knows what happens in the rest of the series.
2014 is the year they should've won it all though. Going into the playoffs, nobody had any business challenging them and they went ice cold and hit a million posts against Montreal of all teams. That hurt too. They'd have run over the Rangers and Kings if they get through the second round.
As for 2019, everything fell right for them in the first round with all the top seeds getting knocked off. They weren't favorites going into the playoffs but after round 1, they probably were. And should've beaten St. Louis soundly if they don't headhunt Grzelcyk in game 2.
In the end, though I think 2009 and maybe 2012 were the more fun seasons and 2013 the most memorable playoff run, 2014 is really the year that you say they absolutely 100% should have won.