Which NHL team is furthest from winning a Stanley Cup?

The parity in this year’s NHL is borderline unprecedented. Almost every team remains in the playoff hunt somehow. It’s thus tougher than usual to understand whom the contenders and pretenders are.

Still, I want to revisit an annual question for the Roundtable. Which NHL team do you feel is furthest from a Stanley Cup right now? 

MATT LARKIN: My angle of attack for this question is always: which team is only just beginning the journey toward bottoming out? In my mind, the in-denial franchises are worse off than the lottery contenders, because the in-denial clubs are years away from accepting their fates and beginning to accrue assets for their next generation. The Toronto Maple Leafs earn that dubious honor from me. They’ve slowly become an older, slower, defensively weaker team with each year since Brad Treliving took over as GM. A more pugilistic Toronto team had a shot to make a deep playoff run…but that shot was last year. With Mitch Marner gone, the team’s best Stanley Cup window shrunk. Now a perennial contender has downgraded to more of a Wildcard-caliber team. With Auston Matthews and William Nylander still in town, the Leafs will remain competitive enough to compete in the murky middle, so any teardown – and march toward the next era of true Cup contention – might be half a decade away.

SCOTT: I certainly agree with Matt’s take on Toronto, but I’m going to go a similar route with the Winnipeg Jets. Outside of some defensive improvement last season (only to go the opposite direction this season), this Jets’ core’s legacy will be a team that struggled to drive play and was carried to the playoffs every year by Connor Hellebuyck’s excellent goaltending, great offense from Mark Scheifele and Kyle Connor, a stellar blueliner in Josh Morrissey and having a play-driving second-line led by Nikolaj Ehlers. This year has proven that removing one of those pieces in Ehlers was detrimental to their success, so then losing Hellebuyck to injury took the floor out from underneath their Cup window. They also lack enough significant prospects to inject into the team to improve right now. Look at their draft record since 2016. Only Dylan Samberg and Cole Perfetti are consistent mainstays making an impact in Winnipeg. And somehow Kevin Cheveldayoff has never been on the hot seat despite having few accomplishments in his time as general manager. I guess if the Jets continue to be this bad, then I’ll be wrong here, because they’ll get a top draft pick which could rejuvenate the team this year. But I feel like Hellebuyck, Scheifele, Connor and Morrissey will be just good enough to get them back into the murky middle this season and keep them as the Stanley Cup pretenders they’ve been for five-plus years until Hellebuyck’s game falls off. At that point, they’ll be able to rebuild, but that could still be another five years out.

ANTHONY TRUDEAU: There are cores around the league that have probably missed their last, best shot, including Toronto, Winnipeg, and the New York Rangers. What those clubs do have is enough very good or great players to fool themselves into trying again. They have clearly identifiable plans to win the Stanley Cup, if not very inspiring ones. After four-and-a-half seasons of existence, the Seattle Kraken still haven’t gotten that far. No team pursues third-line forwards or second-pair defensemen with greater enthusiasm, and the result is a team that’s too good to draft a true star and too bad to compete. Don’t get fooled by the Kraken’s sudden surge into a playoff position, either; strong goaltending (.904 team SV%, fifth) that covers for brutal even-strength hockey (43.6% expected-goal share, last) has been a hallmark of the murky middle since time immemorial.

PAUL PIDUTTI: The NHL really is in a strange place right now where only a handful of deep, legitimate threats exist. With the Central Division situation in mind, I’ll take the St. Louis Blues. Yes, they looked dead in 2019 and went on an improbable run. But I just don’t see a path for this group to relevance any time soon. Just within their own division, how could they get past all of Colorado, Dallas, and Minnesota in the next half decade? Other division rivals Utah and Chicago are years ahead in stockpiling talent for the future. The Blues are on the playoff fringes right now, and a big second half would only worsen their outlook and ability to add to a mid prospect pool. General manager Doug Armstrong has admirably kept them from tanking, and the Blues haven’t been a bad outfit in nearly 20 years. But Armstrong is signing off in the spring and handing the keys to a rookie GM in Alex Steen with a so-so roster, so-so pipeline and unreliable goaltending. In the summer, I envisioned what the NHL standings might look like in 2030 — sure enough, St. Louis ranked 19th.

STEVEN ELLIS: I’m going with the Vancouver Canucks. I just don’t know where this team goes from here. Their pipeline is just below average at best, and their actual NHL lineup is a total mess. This team was supposed to be set for the future with Elias Pettersson, J.T. Miller, Quinn Hughes, Brock Boeser and Thatcher Demko. Instead, two of them are gone, two of them are underperforming and Demko simply needs goal support (and to stay healthy). There seems to be more discussion about the team’s off-ice issues than on the ice, and the distractions have been hard to ignore. The Canucks are just an absolute disaster, and I’m not sure how they fix it.

MIKE GOULD: The Seattle Kraken aren’t a terrible team, but I don’t think they’re even close to winning a Cup, and they’re too high in the standings to be in position to get a true game-changer anytime soon. I think the Kraken have over-invested on forwards through the draft over their first five years of existence and they don’t have the premier piece they need to build a championship-calibre blueline. At the same time, I don’t see a competitive nucleus with the forwards they’ve added over the years, with Shane Wright and Matty Beniers both falling into the “supporting” category for me as opposed to being true leads. I think the Kraken are far, far away, and I think they’ll need to tear it all down and start over before too long. But we’ll see.

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