Which NHL franchise (team or one from a specific season) over the last 25 years are you most disappointed did not win a Stanley Cup and why?

JOEY: I know they made it to a Stanley Cup Final in 2016, but the fact that the Sharks have never hoisted the Stanley Cup is pretty disappointing. The other California teams (Anaheim and Los Angeles) have each won at least one, but the Sharks just couldn’t get over the hump.

How can you not feel sorry for Joe Thornton, Patrick Marleau, Joe Pavelski and company? Those guys played at a high level for so long and it’s unfortunate that they could never win it all.

Since the start of the 2000-01 season, this is where the Sharks have finished in the Pacific Division standings: first, fifth, first, second, second, first, first, first, first, second, third, second, fifth, third, third, third and second. That’s a lot of good seasons. To have only one Stanley Cup Final appearance to show for it is just brutal.

Even the Vegas Golden Knights, who have turned into a bitter rival for the Sharks, have made it to one Stanley Cup Final and that was in their first year of existence.

What’s even more frustrating for San Jose, is that based on what we’ve seen from them in 2019-20, it looks like their window to win is pretty much closed. Can general manager Doug Wilson turn things around quickly? Maybe. But they don’t even have their own first-round pick this year.

There’s been some great Sharks teams over the last 25 years, but they’d trade all that regular-season success for a single Stanley Cup.

SEAN: I agree with Joey. You can count on two hands how many in the last 15 years that the Sharks have been my preseason Cup winner pick. But I’m going to go in a different direction. The 2010-11 Canucks were a team that conquered demons along the way to reaching Game 7 of the Cup Final.

That Canucks roster was a total package. There were some likable characters (Daniel and Henrik Sedin, Roberto Luongo) and others who played the heel role very well (Alex Burrows, Ryan Kesler, Max Lapierre, Raffi Torres). There was also Kevin Bieksa, who could probably find a place in both groups.

Years of playoff disappointment were carried like baggage heading into the 2010-11 season. After back-to-back Round 2 playoff exits at the hands of the Blackhawks, the Canucks were again Cup contenders, and needed to finally finish the job. They did their part initially, becoming the first team that season to clinch a playoff spot and picking up the first Presidents’ Trophy in franchise history.

Every Stanley Cup championship DVD has those flashpoint moments on the road to a title. The Canucks had that. From their regular season success to Burrows “slaying the dragon” with his overtime series clincher against Chicago in Round 1 to Bieksa ending the Western Conference Final against the Sharks in double OT to Vancouver winning the first two games of the Cup Final against the Bruins. It appeared as if the stars had finally aligned.

We know the rest of the story, but that team was both incredibly fun to watch with the talent on it and so easy to root against given the villains employed on the roster. All they needed was just one win in Boston to change history.

JAMES: Joey beat me to the Sharks, but honestly, I’m glad. In having to dig deeper, it conjured some great/tragic hockey memories and interesting thoughts.

For one: the last two Stanley Cup-winners emptied out metaphorical tonnage of angst. The Blues have been tormented by “almost” basically from day one, when they were pulverized in three straight Stanley Cup Final series (1967-68 through 1969-70) without winning a single game against the Canadiens or Bruins. There’d be ample angst if they didn’t win in 2019, and the same can be said for the Capitals. It’s difficult to cringe too hard at the Boudreau-era Capitals falling just short when Alex Ovechkin won it all, anyway.

My thoughts drift, then, to quite a few Canadian teams that rode high.

It’s tempting to go with the Peak Sedin Canucks, in and around that near-win in 2011; after all, while I didn’t grow up a Canucks fan, many were fooled into believing so because of my handle.

But, honestly, the team that might bum me out the most in recent years is the really, really good Senators teams that fell short of a Stanley Cup. (No, I’m not talking about the group that was within an overtime Game 7 OT goal of being willed to a SCF by Erik Karlsson and a few others.)

The 2005-06 Senators rank among the more galling “What if?” teams for me.

During the regular season, that Senators team scored more goals than anyone else (314) and allowed the third-fewest (211). Dany Heatley and Daniel Alfredsson both enjoyed 103-point seasons, and Jason Spezza (90) probably would have hit 100+ if he played more than 68 games. This was a team that also featured Zdeno Chara, a Wade Redden effective enough to convince the Senators to choose Redden over Chara, and other talented players like Martin Havlat, Antoine Vermette, and Mike Fisher.

The biggest “What if?” there revolves around Dominik Hasek getting injured during the 2006 Winter Olympics, a groin issue that kept him out of the ensuing postseason. Even at 41, Hasek was dominant, posting a .925 save percentage. Ray Emery couldn’t get it done, and the Senators were bounced in the second round.

While the 2006-07 Senators were the rendition that actually made it to the SCF, they no longer had Chara or Hasek on their roster.

Instead of a possible Stanley Cup victory, the memorable images of those peak Alfredsson-era Senators teams were ugly ones. Marian Hossa lying, dejected on the ice after Jeff Friesen beat Patrick Lalime and the Devils won a Game 7 in 2003. Alfredsson snapping at shooting a puck at Scott Niedermayer. And then plenty of unceremonious exits.

For more casual hockey fans, that Senators’ surge will probably be all but forgotten, but it’s really stunning just how talented that team was.

(Side note on almost-Canadian champs: I’ll likely go to my grave believing that Martin Gelinas scored that goal for the Flames.)

ADAM: I want to see great players get their championship, especially when it is the one thing that their otherwise great resume is lacking. The Sedins are obviously in that discussion, as are those great Sharks teams with Thornton, Marleau, Pavelski.

I will add another name to that list: Henrik Lundqvist and the New York Rangers. Especially that 2013-14 team that actually made it to the Stanley Cup Final only to lose to the Kings. I know they lost that series in five games but I still feel like it was a lot closer than that because they literally lost three games in overtime. Lundqvist was outstanding in that entire postseason — and that series — and it would have been the capper on his career.

On one hand, I feel like Lundqvist is absolutely respected for the goalie that he has been. But it still seems like there is a “yeah, but…” that always follows him around because he doesn’t have that championship that will keep him from being remembered as one of the all-time greats at the position. He has been a great goalie, a sensational playoff goal, and was always taking the Rangers to levels that they probably shouldn’t have been at.

So which team am I disappointed didn’t win? At least one team with Henrik Lundqvist on it.

SCOTT: The 2018-19 Lightning were an elite team that not only didn’t reach the Cup Final, they didn’t even win a game in the postseason.

The Blue Jackets won their first playoff series as a franchise in stunning fashion as they won four straight against a big Cup favorite.

The Lightning were a victim of their own regular-season success. With 14 games remaining in the regular season, Tampa Bay secured a playoff spot and had little to play for the rest of the way.

“In the end, it’s just we just couldn’t find our game,” Lightning coach Jon Cooper told reporters after the disappointing finish. “That was it. It had been with us all year, and for six days in April we couldn’t find it. It’s unfortunate because it puts a blemish on what was a [heck] of a regular season.”

The Lightning won 62 games that season and finished the regular season with 128 points. The Bruins, who ended up representing the Eastern Conference in the 2019 Cup Final, finished with 107 points.

“You have a historic regular season doing what we did and have basically a historic playoff in defeat,” Jon Cooper said.

Tampa will always be one of the most successful teams to not win the ultimate prize.

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Sean Leahy is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @Sean_Leahy.