Edmonton Oilers: Peter Chiarelli Under Pressure After McDavid Extension

After the record setting Connor McDavid extension, Edmonton Oilers general manager Peter Chiarelli is under pressure to win with his generational talent.

The pressure of being an NHL general manager is immense. In today’s “what have you done for me lately” league, one terrible mistake, signing or trade can ensure one’s ticket out of town. That’s a painfully small margin for error. Edmonton Oilers general manager Peter Chiarelli will be facing this pressure after signing Connor McDavid to a record setting nine figure extension.

Whatever he did to get McDavid to sign for less than the league maximum ($15 million), good for him. It makes his job a little bit easier from here on out. But Chiarelli’s future will be tied to the success of the Oilers with McDavid. Due to the NHL salary cap, he’ll have to make smart decisions about who to keep and who to let go.

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Looking back at his history, Oilers fans should be a little bit concerned. Typically, general managers under pressure are suckers for the “last piece of the puzzle” trade. Trades for that one last piece the team needs to win the Stanley Cup. Recent examples include the Martin Hanzal and Kevin Shattenkirk trades from the trade deadline.

Chiarelli’s history with huge trades is not good at all. Let’s review each of his major trades, both with the Boston Bruins and Oilers.

Phil Kessel Trade

In a vacuum, Chiarelli won this trade by a landslide. As a return, he got the picks that he selected Tyler Seguin, Dougie Hamilton and Jared Knight with. While the last was a bust, the first two provided the Bruins with a lot of value. But here’s the issue. Chiarelli later traded the first for an unimpressive return. Hamilton got traded too, but let’s be fair, that was Don Sweeney who traded him.

Seguin Trade

Bruins fans, you need a hug. This trade was awful for so many reasons. But I’ll just focus on the return. For Seguin, Rich Peverley and Ryan Button, the Bruins got Loui Eriksson, Rielly Smith, Matt Fraser and Joe Morrow. This trade was made in 2013 and none of them in Boston anymore. That’s really all that needs to be said.

Taylor Hall Trade

Look, I understand this trade. It made sense for the Oilers. Think of it like this. Imagine you have a Ferrari. It’s everything you could ask for in a sports car. But suddenly, your family grows. You no longer need the Ferrari, so you trade it in for a Honda Odyssey minivan. Taylor Hall is the Ferrari, Adam Larsson is the minivan.

Edmonton Oilers

While Chiarelli filled a huge need by getting Larsson, Chiarelli deserves to be chastised for awful asset management. Hall deserved a much bigger return than just a solid defenseman. So Chiarelli didn’t really lose this trade in terms of filling a hole, but he did because of asset management.

Let’s be fair to Chiarelli, though. He is very good at tinkering. Chiarelli usually does well with the minor trades. He got Patrick Maroon for next to nothing, and viola, he’s a 30 goal scorer. Chiarelli took a chance on a talented, but troubled, forward in Zach Kassian. So far, so good. The Cam Talbot trade falls in this category because Chiarelli paid an appropriate price for a backup goalie who had yet to prove himself. It’s safe to say Talbot has proved himself. Even the David Desharnais for Brandon Davidson trade made a ton of sense.

Chiarelli must get the Leon Draisaitl extension done now. And it’s not nearly as simple as it sounds. How much money do you invest in someone whose value may or may not be tied to McDavid? In a year, he’s got to worry about Patrick Maroon and Mark Letestu. After the 2018-19 season, Chiarelli has to keep Talbot.

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God speed, Peter Chiarelli. Every move you do from here on out will be judged by whether or not you are the best team in the NHL. By whether or not you win an award that only one team each year can win. Because that’s the way life is for a general manager on a must win team.