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WWYDW(FE): Armchair GM The Trade Deadline

The Oilers have put themselves in an excellent position at the All-Star break as they sit in a tie for fifth in the Western Conference. But, as well as they’ve played thus far, nothing is guaranteed. What Ken Holland does at the trade deadline will play a big role in what happens down the stretch in the incredibly unpredictable Western Conference.

The trade deadline is one month from today, so while the Oilers enjoy their much-needed break and we sit here anxiously awaiting the stretch drive, let’s play armchair GM. In this What Would You Do Wednesday FRIDAY EDITION, here are three deals that I would make if it were up to me…

Deal 1: Trade Raphael Lavoie, Joel Persson, Jujhar Khaira, and conditional 2020 first- and third-round picks to the Ottawa Senators for J.G. Pageau and Ron Hainsey.

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The first-round pick is protected and becomes a 2021 first-round pick if the Oilers draft top-10 in the 2020 draft. If the Oilers re-sign Pageau OR win a playoff round, the 2020 third-round pick becomes a 2020 second-round pick. If the conditions aren’t met and the Oilers give their 2020 third-round pick to Calgary as a condition for the Lucic for Neal trade, it becomes a 2021 third-round pick. Ottawa retains 50 percent of the cap hits.

I tried to base this deal around the Taylor Hall deal the Coyotes and Devils struck, as Hall was the top rental on the market this season. Arizona gave up three prospects and two draft picks with similar conditions. Ottawa gets two quality prospects, a reclamation project roster player in Khaira, and a couple of top draft picks while the Oilers have some security on the picks based on the success they have.

Pageau immediately gives the Oilers a very, very good third line, making their lineup significantly deeper in the process. He’s a proven playoff performer who can play a strong defensive game while also providing offensively. Through 49 games, Pageau has already tied a career-high with 19 goals this season. He also has far and away the best plus/minus on the roster despite playing heavy defensive minutes.

Hainsey, another rental, is a veteran with Stanley Cup pedigree. Given the question marks surrounding Matt Benning after his concussion, finding a solid, right-handed defenceman to play on the third pair is important. Hainsey is logging 20:04 per night with the Sens this year and is a positive in terms of goal differential despite playing heavy defensive zone minutes.

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This would be the trade deadline splash we haven’t seen the Oilers make since 2006. Much like that year, the team is currently on the bubble, but it seems worthwhile to take a gamble on what could be a magical year. I would also pish hard to re-sign Pageau, much like the team did with Dwayne Roloson after trading for him.

Holland avoided using the first-round pick in a Taylor Hall trade, but Pageau seems like a better, more multi-dimensional fit for the Oilers.

Deal 2: Trade Cooper Marody and a 2020 fifth-round pick to the Los Angeles Kings for Kyle Clifford. Los Angeles retains 50 percent of the cap hit.

Looking through deals made over the last few seasons, trades for depth rental players like Clifford are all over the grid. A deal I found that seemed somewhat similar last year was Ben Lovejoy going from New Jersey to Dallas for Connor Carrick and a third-round pick.

In exchange for a solid depth player, the Kings get a close-to-NHL ready prospect and a scratch ticket of a draft pick. It’s hard to imagine a fourth-liner getting more than that at the trade deadline. Meanwhile, the Oilers add some quality veteran depth to their bottom-six in the form of Clifford who has two Stanley Cups on his resume.

Sep 17, 2018; Calgary, Alberta, CAN; Edmonton Oilers left wing Tyler Benson (49) during the first period against the Calgary Flames at Scotiabank Saddledome. Mandatory Credit: Sergei Belski-USA TODAY Sports

Deal 3: Call up Tyler Benson. This isn’t a deal, per se, but I think it’s a necessary thing for Holland to do down the stretch. We’ve spoken at length about how the Oilers need to acquire wingers for their top-six, but, as Kailer Yamamoto has shown, that upgrade could very easily already be in the organization.

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Benson has been playing excellent hockey for the Bakersfield Condors and could nicely fit alongside Connor McDavid and Zack Kassian on the team’s top line. That would slide James Neal down the lineup where he isn’t playing as many minutes. If Benson isn’t ready, he can go back down, Neal can slide back up to the top line, and Kyle Clifford can play on the third line.

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Here’s what I have after all of my deals…

Tyler Benson – Connor McDavid – Zack Kassian

Ryan Nugent-Hopkins – Leon Draisaitl – Kailer Yamamoto

James Neal – J.G. Pageau – Josh Archibald

Kyle Clifford – Riley Sheahan – Alex Chiasson

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Sam Gagner, Gaetan Haas

Oscar Klefbom – Adam Larsson

Darnell Nurse – Ethan Bear

Kris Russell – Ron Hainsey

Matt Benning

Obviously, it’s really, really difficult to come up with trade ideas that make sense for both sides from your armchair. That’s why I tried to go on similar deals that we’ve seen in recent history.

My goal, ultimately, when finding trades for the Oilers was avoiding giving up young NHL-ready talent in Kailer Yamamoto and Tyler Benson while also hanging on to the organization’s top two prospects in Phillip Broberg and Evan Bouchard. The reality involved giving up a lot of draft pick capital this spring and some other quality prospects. But you can’t have it all and you have to give to get. Given Edmonton’s situation, I would rather hang on to already-drafting-and-developing talent than picks in this summer’s draft.

The Oilers have worked incredibly hard to put themselves in a position to make the playoffs this spring, so it’s important that Ken Holland rewards them. Acquiring Pageau, Hainsey, and Clifford, in my mind, gives Edmonton a deep enough roster to not only make the playoffs but also possibly do some damage in a wide-open Western Conference.

What say you, Nation? How do you approach the trade deadline? What deals do you have in mind? 

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