The word “generational” is thrown around far too often.
Sure, there are generational scorers like Alexander Ovechkin and Auston Matthews, as well as generational defencemen like Cale Makar and Erik Karlsson. However, generational means once in a generation, and there can only be one generational talent in their prime at the time.
As of right now, Connor McDavid is the clear generational talent in his prime, with Connor Bedard being pegged as the next generational talent. Bedard, who is in his sophomore season, has 11 goals and 37 points in 41 games for an awful Chicago Blackhawks team. Even McDavid had a bit more firepower around him at this point in his career.
Going back in time to 2016, McDavid was the next player to be pegged as generational, while Sidney Crosby was in his prime. The Cole Harbour native was a few months removed from winning his second Stanley Cup, as well as his first Conn Smythe Trophy.
McDavid unfortunately missed both matchups against the Pittsburgh Penguins in his first season, as he broke his clavicle in early Nov. 2015, a few days before the Penguins and Edmonton Oilers were set to meet. However, the first matchup between the two generational talents didn’t disappoint.
It was a different Conor to open the scoring, as Penguins forward Conor Sheary scored about two minutes into the game to give the defending Stanley Cup champions a 1-0 lead. However, Jordan Eberle tied it with his fourth of the season with about five and a half minutes left in the opening frame, with McDavid picking up the primary assists.
Less than three minutes later, Patrick Maroon scored his fifth of the season to give the Oilers a 2-1 lead, with McDavid getting the primary assist once again. The scoring stayed the same until the second period.
Just three minutes and 20 seconds into the middle frame, Eberle scored his second of the game with the primary assist going to – you guessed it – McDavid. However, the Oilers were taking on the reigning Stanley Cup champions and the experience showed, as the Penguins rallied back with three unanswered goals to take the first McDavid/Crosby showdown 4-3.
The Penguins were in a contention window early in McDavid’s career and they won the first six matchups. In the next matchup they played that season, the Oilers fell 3-2 in a shootout that featured one of the most exciting three-on-threes I’ve ever witnessed with Crosby being held pointless for a second consecutive game between the two teams. The Penguins won the next four games, with Crosby picking up two goals and six points in the first six matchups. On the other hand, McDavid scored three goals and 10 points in the first six matchups. 
As McDavid and the Oilers got better, the matchup started to turn in favour of the Oilers. Edmonton has won the last eight matchups between the two teams, with McDavid scoring six goals and 17 points. Crosby in those eight games has been held to a goal and three points.
It’s becoming increasingly clear that the Oilers and Penguins won’t match up in the Stanley Cup Final. Crosby is in the twilight of his career (and still producing at a great pace), but the Penguins are currently tied for the final Wild Card spot. Even if the Penguins make the postseason, they just aren’t as good as they were early in McDavid’s career.
The Oilers are, of course, as they fell two goals short of winning the Stanley Cup last playoffs against the Florida Panthers. However, there was a pathway for the two teams to meet in the 2017 Stanley Cup Finals. While the Oilers fell short on Nov. 8, 2016, they went on to finish with a 47-26-9 record with 103 points, breaking an 11-season postseason drought.
In the first round, they faced the San Jose Sharks, who fell to the Penguins in the Stanley Cup Finals in 2016. The inexperienced Oilers defeated the Sharks in six games, moving on to the second round where they faced the Anaheim Ducks. Unfortunately, McDavid’s first postseason run came to an end (you can read more about that here), while Crosby and the Penguins went on to defeat the Nashville Predators to win back-to-back Stanley Cups.
On Thursday, McDavid and Crosby go face-to-face for the 15th time. The youthful McDavid has had the upper hand in the production category, while the Oilers have won the past eight matchups. With Crosby towards the end of his career, there’s only going to be a few more of these matchups between the two generational talents remaining. Savour it while you still can.
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