Oilers Have Opportunity to Make 4 Blockbuster Pre-NHL Deadline Deals

It would require the Edmonton Oilers to pull out a little of the same magic Kevin Lowe found in 2006 when he added numerous pieces and the team made a run to the Stanley Cup Final, but GM Ken Holland has an opportunity to make at least three big deals ahead of the 2022 NHL Trade Deadline that could make the club immediate contenders.

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If the franchise wants to be considered a serious threat this season, they know they need better goaltending, a top-six goal scorer, and another left-shot defenseman. If they can add a depth center, even better. There is the potential for moves that could work if the cards fall just right and while making all of these moves this season would be next to impossible, that doesn’t mean it can’t be done.

Oilers Could Land Their Rental Goaltender

Marc-Andre Fleury’s name has been linked to the Oilers and while it’s not clear how real those rumors might be, a trade could work if the Blackhawks and Fleury see the potential fit in Edmonton. The salary cap is an issue, unless both the Blackhawks and another team retain salary. Should that happen, Fleury becomes available at a prorated cost of $1.75 million.

Marc-Andre Fleury, Chicago Blackhawks
Marc-Andre Fleury, Chicago Blackhawks (Photo by Brian Babineau/NHLI via Getty Images)

A pure rental, the Oilers would have to give up a first and another draft pick, plus either bury or move Mikko Koskinen’s contract. It’s difficult but doable, assuming Fleury approves the trade.

Fleury will immediately improve the outlook for the Oilers in goal. A trio of he, Mike Smith and Stuart Skinner would work and answers many of the questions Edmonton has in that regard. So too, because the Oilers have recent trade history with the Blackhawks and a conditional pick still part of the Duncan Keith trade, it’s reasonable to assume more business can be done between the two teams if Fleury is up for another temporary move.

The Blackhawks will have teams asking about Fleury so the Oilers are guaranteed to lose at least two draft picks or their first-rounder and a decent prospect (going to the third team). There’s no way around that if Holland wants to make the move. Remember, Holland isn’t just competing with other teams for the player, he’s got to wet the beak of a third team helping the deal along.

Oilers Could Land Ben Chairot

The Montreal Canadiens will trade defenseman Ben Chiarot, it’s just a matter of where and for what return? Most believe he’ll fetch a first-round pick and if the Oilers move theirs in the Fleury deal, the best Edmonton can do is move their 2023 first-rounder. The alternative is to convince Montreal to part with Chiarot for a second-rounder and a prospect. If the prospect is good enough, it’s workable.

Ben Chiarot Montreal Canadiens
Ben Chiarot, Montreal Canadiens (Jess Starr/The Hockey Writers)

Phillip Broberg immediately comes to mind, and most fans won’t like the idea of moving a future blue line staple for a rental, but the team’s move towards Markus Niemeläinen as a regular could be telling. If Holland likes the element Niemeläinen brings and with other prospects in the system, the Oilers could move Broberg and the Canadiens would be intrigued.

Related: 5 Canadiens Who Should Be Moved at the 2022 Trade Deadline

The reality is, choosing a top-notch goaltender or a reliable and experienced defenseman is what Edmonton will have to do. It’s not likely the team can have their cake and eat it too. That said, if the Oilers are willing to get creative and offer up something the Canadiens might find more appealing than a first, it’s possible. Again, the Canadiens will likely need to retain salary in the deal and that’s why Edmonton doesn’t get away with less than a decent pick and a prospect like Broberg.

Sign Evander Kane

One of the few deals that won’t cost the Oilers significant assets is the signing of a player like Evander Kane. After clearing unconditional waivers on Sunday, the San Jose Sharks are going to begin the process of terminating his NHL contract, a move that would make him a UFA. If he sees the Oilers as an opportunity to rehabilitate his career, there’s a lot to like about the idea of playing Kane in a top-six role with either Connor McDavid or Leon Draisaitl.

Colorado Avalanche's Cale Maker Philipp Grubauer San Jose Sharks' Evander Kane
Colorado Avalanche’s Cale Maker watches as San Jose Sharks’ Evander Kane scores on Colorado Avalanche goaltender Philipp Grubauer (AP Photo/Josie Lepe)

The Oilers will have to decide if Kane is worth the risk as his off-ice antics have been well documented. If a number of teams don’t want to go near the potential mess that is Kane in their locker room, there’s an opportunity for this to be a short-term home run.

I’ve made plenty of arguments about why I’d consider this. You can see those here.

Sign Eric Staal

He’s not found a team willing to sign him, but Eric Staal absolutely wants to keep playing in the NHL this season. While his preference is to play for a US team, his options are running out and he’s played with Canadian clubs in the past.
Could he be the third or fourth-line center the Oilers could use, splitting time with a player like Ryan McLeod? This is a league-minimum gamble for the Oilers, at best.

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Staal doesn’t fall under the category of “blockbuster”, but he could be considered a difference maker. He’ll be motivated, rested and experienced. Even if he’s not giving you everything you want on the ice, in limited minutes he should be effective and he’d be a strong presence in the locker room.

Is It Worth It?

If the Oilers can pull off most of these moves, it means mortgaging a good chunk of the team’s future, thus it’s fair to ask if it’s worth it. Theoretically, the Oilers would be moving this year’s first, a second (probably next year’s), Philip Broberg, Koskinen, and at least one roster player to make space (potentially someone like Kailer Yamamoto), while probably another draft pick in a later round. In exchange, the Oilers get Fleury, Chariot, Kane and Staal, with absolutely no guarantee any of them staying after this season.

It’s a big price to pay and two other teams need to be willing to play ball. The Oilers would be bringing in around $5 -$6 million — Fleury ($1.75 million), Chairot ($1.75- $2 million), Kane ($1 million), Staal ($750K million) — with about the same amount going out should the team move Koskinen ($4.5) and Yamamoto ($1.175).