Will 2020 Stanley Cup be the toughest ever to win?

During the latest episode of “Our Line Starts,” Keith Jones and Patrick Sharp argued that the 2020 Stanley Cup might just be the toughest to ever win.

However you feel about that, others argued similarly. Back in mid-April, Golden Knights forward Max Pacioretty also argued that the 2020 Stanley Cup might require the most from players.

“I think this will be the hardest Stanley Cup to win out of all of them,” Pacioretty told Gary Lawless of the Golden Knights’ website. “Look at all the obstacles. Who knows when we’re going to play, where, fans or no fans, everything is up in the air …”

Again, Pacioretty made that observation in April, before the NHL announced its return-to-play plans. Jones and Sharp argued their point with more information about the process. The larger arguments remain pretty similar, though.

Of course, as Jones and others also note, there are still a lot of hurdles to clear. Laying out a play to hand out the 2020 Stanley Cup doesn’t mean you’ll reach that destination.

But Pacioretty and others provide some room for debate. Could a run for the 2020 Stanley Cup prove to be the toughest of them all?

How a run to the 2020 Stanley Cup could be especially difficult

While the sheer uncertainty of the situation provides the best fodder, you could also lean on the nitty gritty details. Consider how difficult the path could be for a Qualifying Round team trying to win the 2020 Stanley Cup.

Said team would jump into a high-stakes, best-of-five series with a potentially dangerous opponent. Only then would they make the typical “Round of 16” you’d associate with the postseason.

The NHL hasn’t announced how long each (traditionally best-of-seven) First Round and Second Round series would be. However, we do know that the league aims for best-of-seven series during the Eastern and Western Conference Finals, along with the 2020 Stanley Cup Final.

So … yeah, that could present a treacherous path. Especially for teams in that Qualifying Round, but Round Robin teams like Pacioretty’s Golden Knights wouldn’t have it easy, either. And that’s before we get into the logistics of living in a hub city, potentially away from family, friends, and other comforts.

NHL seasons have faced other extraordinary/unusual challenges

Yes, these are strange times — in some ways, unprecedented — but the NHL’s seen other serious challenges.

As you may know, the league faced serious disruption from another epidemic. The 1919 Stanley Cup was not awarded thanks to “The Spanish Flu.” (Gare Joyce recently looked back at that, and how it may illuminate the league’s struggles with COVID-19, for Sportsnet.)

If the NHL manages to award the 2020 Stanley Cup, it won’t be alone in the league forging on during tough moments. Back in 2017, Stan Fischler looked back at the NHL operating during World War II, and all of the challenges that ensued.

Each team had many players who were on active service during the war. In hockey’s “Victory Lineup” at the start of the 1942-43 season, the Boston Bruins had 16 players, the Canadiens 11, the Chicago Black Hawks seven, the Brooklyn Americans eight, the Detroit Red Wings eight, the New York Rangers 19 and the Maple Leafs 14.

Pacioretty himself weighed the significant challenges of going for the 2020 Stanley Cup with some unusual advantages. Most obviously, players will be as healthy as they’ve ever been this late in a season.

Considering how people often complain of rigorous travel, one perk of the “hub city” system would involve far more limited movement. (From a quality of life standpoint, that’s probably mostly negative. Players would prefer to see friends and family, and the comforts of home. But still, it’s worth at least mentioning in passing.)

2020 Stanley Cup not the only unusual circumstance

Thanks to lockouts and/or lockout-shortened seasons, we’ve also seen players enter postseasons in less typical circumstances. Sure, some will worry that the 2020 Stanley Cup winner might get the “asterisk treatment.” There are people who probably still discredit, say, the 2005-06 Hurricanes for winning it all during an unusual season.

Overall, Jones, Sharp, and Pacioretty all have decent larger points. The sheer uncertainty of this situation should make it difficult. That’s especially true for the NHL players who are most aptly “creatures of habit.”

Panthers defenseman Anton Stralman candidly spoke about the many obstacles the NHL faces in determining a 2020 Stanley Cup winner while managing risks. It won’t be easy to win it all, but then again, it rarely is, right?

Check out the full episode of “Our Line Starts” below:

James O’Brien is a writer for Pro Hockey Talk on NBC Sports. Drop him a line at phtblog@nbcsports.com or follow him on Twitter @cyclelikesedins.

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