The biggest talking point that will surround the Edmonton Oilers organization this summer will be the future of Leon Draisaitl in Edmonton and by extension, Connor McDavid's. Draisaitl has one more year left on his 8.5 AAV contract while McDavid has two more years left on his 12.5 million dollar AAV deal. We know the cap is going to start to increase at a larger rate again, likely by at least 4 million dollars next season and probably by more the following year.

That means that contract sizes will continue to skyrocket. We've already seen some of that this season with players like Matthews (13.25), Nylander (11.5), and Pettersson (11.6) all getting their pay raise.

The reason this conversation is getting kicked up right now is because of recent comments from insider Darren Dreger, debating how likely it is that the German forward will sign right away in the off-season.

Now, let's start by saying all of this talk is far too premature. Whatever success or failure the team has in the playoffs this season will likely be a strong factor in Leon and the organizations decision moving forward. That all being said, there is still value in at least looking ahead and recognizing some of the elements and factors when considering either an extension or a trade.

The McDavid Factor

Let's start with Connor McDavid. Assuming Draisaitl wants to stay in Edmonton and McDavid wants him to stay in Edmonton than everything else is moot. The Oilers will offer Draisaitl a blank check if it means that McDavid is happy and will also sign an extension. I think of years ago when Crosby took a 8.7 million dollar deal and the following year Malkin took the exact same deal. It was the organization saying these are our guys for the long haul. Some might argue that a 15 million dollar AAV for Draisaitl would be too high but not if it means signing McDavid at 15 million as well.

Short Term Deal

Second, I don't think we are talking about an 8 year deal for any side here. We are starting to see elite players like Matthews look at shorter term deals, knowing the cap will continue to increase. Matthews knows that while he might be valued at 13 million for the next few years, when he goes to sign again it will likely be 17 or 18 million.

Assuming the plan is to extend Draisaitl, when does it need to happen? The answer has to be in the off-season. The Toronto Maple Leafs took a massive gamble with Nylander in not getting a deal done prior to the season starting. Luckily for the Leafs (and Nylander) the winger exploded with a career year and agreed to stay in Toronto, cashing in on his production.

The Leafs avoided the worst case scenario. Imagine not signing Draisaitl and going into next season with him set to be a UFA. Draisaitl has another great season and the Oilers are in the playoff picture. There is no way the GM is going to trade one of his top players at the deadline when they are pushing for a Cup, the Oilers go into the playoffs, lose in the third round and Draisaitl walks in Free Agency, leaving the Oilers with nothing for one of the best players in the NHL.

NEW GM

One key reason I don't see the above happening is that Edmonton is going to have a new GM after this season is complete. Ken Holland is in the last year of his deal and President and CEO Jeff Jackson is going to want to bring in his own guy, like he did with Knoblauch. Whoever this GM is, cannot have their first big piece of business be losing Draisaitl for nothing. If Leon wants to sign, get it done. If he doesn't want to commit, you have to trade him.

WHAT DOES A TRADE LOOK LIKE?-

So, all attempts to entice Draisaitl to extend have failed and the player and agent have laid out their intention to explore Free Agency. What does trading Leon Draisaitl, the player with the third most goals and second most points over the past three years look like?

OPTION 1 - THE BLOCKBUSTER 1 FOR 1
Option 1 is finding a singular player whose value is on par with Draisaitl. I am not saying either side would do this trade but we are talking Rasmus Dahlin for Leon Draisaitl. The Sabres get an elite centreman and the Oilers get an elite defenseman. These types of trades are typically not realistic because these types of players are often considered organizational cornerstones and almost untouchable.

OPTION 2 - THE MULTIPLE PLAYER TRADE
This is the most likely option and the one that likely would benefit the Oilers the most in the long run. Imagine trading Draisaitl to the Bruins in exchange for Charlie McAvoy and Pavel Zacha, or Dylan Cozens and Alex Tuch.

Now before anyone runs to the comment section, please note I am just throwing out player names as an example. To put it in more general terms, the Oilers would be trading Leon Draisaitl, an elite level player in exchange for a decent top six centre and really good defenseman, or for a young and rising top six centre and good winger.

The Oilers would "lose" this trade in that they are giving up the best player but could end up being a better team by addressing multiple holes in the roster. What is better, having one elite 12 million dollar player or having three solid 4 million dollar players? Depending on who those players are I think there is an argument for both.

Also for any of the above options, I think that a Draisaitl extension must be part of the deal. As elite a player that Draisaitl is, I don't think any team is giving up a large package for a rental. That is also in the Oilers best interests as an extension massively increases their own return.

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For now, we are going to focus on tonight's game against the Jets, followed by the rest of the regular season, followed by the post-season. There is plenty of time to make a decision but eventually we are going to know what that decision is and how it will effect this organization moving forward.

Thanks for reading.

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