If there's one thing the Edmonton Oilers should have learned from this past season and a disappointing early exit from the playoffs, it's that there's no longer space to take Connor McDavid's contract for granted. 

When the best player in the world chose not to take a raise, the Oilers got a gift from their captain. They turned around and squandered it.

One could argue they did worse than nothing, making the team weaker after being as close as it gets the previous two seasons, then being blessed with one of the better contract deals in the NHL. 

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McDavid spent most of this past summer deciding on his contract. In the end, he signed for two more seasons at the exact same money. The explanation was that he wanted to give the core another window to make a run at the Stanley Cup, leaving millions on the table for management to fill holes around him. He didn't just badly want to win; McDavid wanted to ensure Leon Draisaitl, Darnell Nurse, Zach Hyman, and others were along for the ride. 

What did the Oilers do? 

GM Stan Bowman made questionable move after questionable move. He signed Trent Frederic to an eight-year contract. He gave Jake Walman seven. Both were arguably overpaid when the market dictated deals were available. He also traded Stuart Skinner for Tristan Jarry (who is locked in for two more seasons) and let depth guys walk, while not really recovering from two offer sheets the organization handled poorly and still likely regrets. 

Not every decision was a bad one, and Bowman is not the only GM to have signed a bad deal or two. However, the pressure not to mess up following McDavid's gesture and with the team's window to win was unique to his position. It was essential that he not look a gift horse in the mouth.

To say the least, he didn't take advantage of a golden opportunity. 

Fast forward a few months, and both Draisaitl and McDavid noted they've got concerns. Agreeing that the team took a step back this season, they have ground to make up, and it's incumbent upon Bowman and the organization to get better. It's going to be a challenge and interesting to see if either superstar trusts this management team to make the important decisions. 

Frankly, why would they? 

The good news is that Draisaitl is locked in. He's less of a concern to bail, and the fact that he's building a brand-new house in Edmonton suggests he has no plans to go anywhere.

McDavid is another story. 

He gave the Oilers a clear window. Beyond two years, there was no guarantee, and for Edmonton, the window isn't even that wide. Two more seasons is just what he can play before he's got the choice to leave. If he loses faith in the organization, he'll be able to handpick his next stop. The Oilers can't let it get that far. They'll need to get another commitment from him well before the day he can test free agency. If there's any indication he'll be open to doing so, the Oilers need to talk trade with other teams. 

This season proved the Oilers are not close enough to being a contender to afford letting McDavid play out his contract year in an effort to make a Stanley Cup run. Before this early exit, that might have been on the table -- risk McDavid leaving if the Cup was a real possibility.

It wouldn't have been ideal to play a season with McDavid's future up in the air, but if Edmonton was on the cusp, it could have been an acceptable calculated risk. Worst-case scenario, he sees no reason to walk, nor does he see another team with a better chance of winning. 

The way this current team is assembled, all of that is now gone.

If he's not sold on the team's future or his trust in management to make this roster better has eroded, there's no reason for him to commit again. He definitely won't be quick to take a deal. Sure, Edmonton will gladly give him what he's worth, but what if that's not even enough? Money is clearly not his priority. Winning is. 

In Edmonton, it's a neck-and-neck race between winning and asset management.

Trading McDavid would allow the Oilers to acquire multiple pieces that could improve the team. It would give management a chance to dump bad deals as part of the blockbuster transaction. If McDavid doesn't commit, the Oilers can't afford to drop the ball again. They're not a good enough team to ride out his decision and try to win.

Using all of McDavid's current deal to make playoff runs without certainty on his future is not an option management should consider now. That means this summer has become one of the most important in the franchise's history. 

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