After a decade of darkness, the Oilers had an excellent season, winning 47 games, beating the San Jose Sharks in the first round, and coming within one win of advancing to the Western Conference Final.
Back in September, if you had asked most people in Edmonton what they wanted out of this season, they would have been happy with the Oilers just playing competitive hockey after the trade deadline. Now? There aren’t any participation medals. It’s the dawn of a new era in Edmonton. With it comes new expectations.
The Oilers took a massive step forward this season, and in order to capitalize on their window of opportunity, they’ll have to take another big one next season. As a template, look no further than the Pittsburgh Penguins, who were in a virtually identical situation a decade ago, landing the golden ticket at the Sidney Crosby Sweepstakes and having their franchise’s fortunes completely changed.
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The Penguins are the gold standard for the Oilers. Through two years, it’s been very similar. Can they continue to follow suit?

How did they get there?

The Penguins weren’t quite as bad as Edmonton was during its infamous Oil Change, but between 2001 and 2005, nobody in the league was worse than Pittsburgh was. The Pens chose Ryan Whitney with the fifth overall pick in the 2002 draft, Marc-Andre Fleury first overall in 2003, and Evgeni Malkin second overall in 2004 after three seasons of finishing with under 30 wins.
The 2004-05 season was lost due to the lockout, and after a new Collective Bargaining Agreement was reached, the league decided to have a lottery decide the order of the 2005 Entry Draft. The lottery was known as the Sidney Crosby sweepstakes because whoever won would have their fortunes turned around immediately by the prospect who had just scored 168 points in 62 games in the QMJHL. 
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The Penguins, with their perfectly-timed years of epic futility, were in a luck. Teams were given lottery balls based on where they finished in the standings in the previous three seasons and whether or not they had chosen first overall in any of the previous four drafts. The Penguins had their ball drawn (unless you believe the conspiracy theories about Gary Bettman giving them the pick behind closed doors) and the rest is history. Sidney Crosby joined a Penguins franchise that already had a solid core of young players, like Malkin, Fleury, Whitney, Ryan Malone, Rob Scuderi, Erik Christensen, Colby Armstrong, and Brooks Orpik.
In 2015, the Oilers drew a magic ticket just like the Penguins did a decade earlier. When they added Connor McDavid, the Oil Change that didn’t seem like it was ever going to end got completely flipped on its head.
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And then what happened?

Crosby came flying out of the gate, putting together a rookie season that nobody realistically could have expected. As an 18-year-old in the NHL, Crosby put up 39 goals and 63 assists, good for sixth in the league in points. Remember, this was the first year after the lockout, back when everything was a penalty and scoring skyrocketed.
Despite his effort, the Penguins were terrible. They finished 22-46-12, a points percentage just as bad as the one they put up in 2003-04. Honestly, it’s incredible Crosby produced at the level he did. The team was bad. The corpses of John LeClair and Mark Recchi were third and fourth in team scoring and their blue line featured names like Josef Melichar and Ric Jackman being fed consistent minutes. For their efforts, though, the Pens were able to draft Jordan Staal with the second overall pick in the 2006 draft.
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The Penguins didn’t do too much over the 2006 offseason, but adding Staal and Malkin, who came over to North America after playing two post-draft seasons in Russia, really added depth to the team’s roster. Crosby had another spectacular season, scoring 36 goals and 84 assists, good for 120 points, which is still his career high, and the Art Ross, Hart, and Pearson trophies. Crosby’s effort, along with strong rookie seasons from Malkin and Staal, helped the Penguins finish with a 47-24-11 record, a massive 47 point improvement from where they finished the previous season. Thanks to the standings, the Pens had to play the Senators in the first round, and were knocked out in five games.
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Again, the Penguins didn’t make any big free agent investments in the 2007 offseason. Their big signings were Petr Sykora, who inked a two-year deal after a strong season in Edmonton, and Daryl Sydor, who, on the final legs of his career, signed a two-year contract. In July, Crosby was inked to a five-year extension worth $8.7 million annually that would eat up the remainder of his control years. The big move came at the trade deadline when the Penguins shipped Colby Armstrong and Erik Christensen, two solid, young depth players the team had developed, along with 2007 first round pick Angelo Esposito to the Atlanta Thrashers for Marian Hossa.
The Penguins finished with a 47-27-8 record, impressive considering Crosby and Fleury were injured for a significant amount of time. They swept Ottawa in the first round, and plowed through New York and Philadelphia, only losing two games. They were eventually stopped by Detroit in the Cup Final in six games by a veteran Red Wings squad.
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The Penguins lost Hossa in the 2008 offseason, but replaced him with two low-key signings, adding veterans Miroslav Satan and Ruslan Fedotenko on one-year deals. They gave Evgeni Malkin a five-year extension identical to the one they gave Crosby the year before. During the season, they pulled the trigger on a major deal, sending Ryan Whitney, who had developed into a good, offence producing top-four defenceman, to the Anaheim Ducks for Chris Kunitz and Eric Tangradi. They also acquired Bill Guerin at the trade deadline from the Islanders.
The biggest change the Pens made, though, was firing head coach Michel Therrien. The team had a 27-25-5 record in February, and replaced Therrien with Dan Bylsma, who led the team to a 18-3-4 finish to the season. They downed the Flyers, Capitals, and Hurricanes before going up against the Red Wings again in the Final, a series they would ultimately win in seven games.
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The Penguins remained competitive the years after their Stanley Cup victory, suffering through some down seasons as Crosby battled concussion issues. But now, with Malkin and Crosby as grizzled veterans in the league, the Penguins are better than ever. They won their second Stanley Cup with this group last spring, and there’s a very good chance they’ll win again this year.

What does it all mean?

The similarities between these two teams are obvious. And so far through two years, this Edmonton team has looked a lot like that Pittsburgh team.
In McDavid’s first season, the Oilers struggled and finished 29th in the league, just like the Penguins did in Crosby’s rookie year. The following year, McDavid led the league in scoring with 100 points, and helped the Oilers to a 103-point season, good for eighth in the league. In his sophomore season, Crosby won the Art Ross and Hart trophies, and the Penguins finished tied for eighth in the league with 105 points. Also, like 2016-17 for Edmonton and 2006-17 for Pittsburgh, both teams saw the emergence of a second elite center in Leon Draisaitl and Evgeni Malkin.
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Crazy, right?
I mean, the comparison isn’t perfect, in that these are different people in a different situation 10 years later, but you know what I mean. McDavid might be as good as Crosby, Draisaitl isn’t as good as Malkin, and while Pittsburgh had a solid group of young players out together before they got their lotto ticket, Edmonton’s years of futility resulted in them having a bigger load of young talent than Pittsburgh ever did.
The goal now, obviously, is to continue this pattern. Pittsburgh made a big step in Crosby’s third season, making it all the way to the Stanley Cup final, then they won it all the following year.
This summer, Peter Chiarelli will get McDavid and Draisaitl, the core of this team’s future, locked up long-term. Draisaitl’s entry-level deal is over, and he has five more years left of team control before he can hit free agency. McDavid has one more year left on his entry-level deal, and the extension he (likely) signs this summer will kick in in 2018-19. If I had to venture a guess, I would say that both players will be locked up at a combined cap hit of between $16-17 million, which is similar to the identical $8.7 million deals Crosby and Malkin were given.
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Beyond that, though? That’s where things get difficult. When the Penguins got over the hump in 2009, they did so after making some hard decisions.
They dealt two important depth players they had developed for Marian Hossa, but realized keeping him around wasn’t going to work financially, and let him walk. That gave them the flexibility to add names like Guerin, Fedotenko, and Satan. They also made a difficult decision on Ryan Whitney, who appeared to be developing into a top defenceman, sending him to Anaheim for Chris Kunitz, who’s worked like magic with Crosby. Another difficult decision was firing Therrien, who wasn’t the right voice for the team, and replacing him with Dan Bylsma, a rookie coach. 
One thing the Penguins didn’t do was go hard in free agency. Like I said, they avoided that big Hossa contract in 2008, which may or may not have worked out for them. Instead, they picked up veterans on short-term contracts and plugged holes around their core with low-key additions. The big deals they handed out were to players they drafted and developed themselves, the ones they identified as core players who meshed with the group.
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Chiarelli has already made some difficult decisions in his two years at the helm. He moved Taylor Hall for Adam Larsson, a one-for-one swap that was maligned by just about everybody. This summer, he has more tough choices to make. Are Ryan Nugent-Hopkins and Jordan Eberle long-term fits? Does this blue line need another piece? Which veterans can be plugged into the lineup? Where are they going to come from? Are there any worthwhile free agents even available?
There isn’t one specific way to do this, but the Penguins offer a nice blueprint for the Oilers to follow. The two teams have shown a lot of similarities so far through Connor McDavid’s first two seasons, and if Chiarelli plays his cards right, the next two years will be similar too. The bar has been set high, but it’s a realistic one. If two years from now the Oilers haven’t made it out of the Western Conference, something has gone wrong. 
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