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Peter Chiarelli’s Oilers: The 10 Worst (And 5 Best) Moves He’s Made As Edmonton GM

Peter Chiarelli's Oilers seemed to be on the right path but have taken a big step back this year. What is going on in Edmonton?

April 18, 2015 was a big day for the Edmonton Oilers organization. That’s when the club lucked out at the annual draft lottery, securing the first overall pick and with it the right to draft generational talent Connor McDavid.

The Oilers were a terrible team at the time of the draft lottery, but everything changed that day. At the time Craig MacTavish was GM of the Oilers, but he was clearly in way over his head, so the Oilers went out and hired (who they thought) was a legit general manager in Peter Chiarelli.

They were the same old Oilers in 2015-16—McDavid’s rookie year in which he missed nearly half the season due to a broken clavicle—finishing 29th in the league. But, 2016-17 offered hope, as they made it to the postseason for the first time in a decade and advanced to the second round.

While fans thought they’d turned the corner and had years and years of competitive hockey with McDavid at the helm ahead of them, early returns on 2017-18 show that may have been a bit premature. A series of moves made by GM Chiarelli appear to have handcuffed this club, and today’s list takes a close look at 15 moves Chiarelli’s made since becoming GM in Edmonton.

Since we like to be fair here at TheSportster, we wanted to point out both bad moves and good moves. And since Chiarelli has erred far more than succeeded, we had to go with 10 bad moves and five good ones. Here they are, in order of least bad/least good to worst/best. Enjoy.

17 Bad: Nail Yakupov Trade

Sergei Belski-USA TODAY Sports

This isn’t an egregious error by any stretch of the imagination, as Nail Yakupov was simply not working out in Edmonton. The former 1st overall draft pick from 2012 struggled to find consistency, and perhaps was partially ruined by former Oilers coach Dallas Eakins. Chiarelli held onto Yakupov for his first season in the driver’s seat, but decided he’d seen enough and dealt him to St. Louis prior to 2016-17 for Zach Pochiro and a 3rd round pick.

Yakupov started out hot in St. Louis, but tapered off in a big way and basically ended up a healthy scratch for the bulk of the year. The Avalanche signed the enigmatic Russian to a one-year deal this past offseason, and it looks as though Nail is maybe starting to figure it out. Either way, the Oilers are terribly shallow on the wing and Yakupov would actually improve the club there today, sadly.

16 Bad: Milan Lucic Contract

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Oh, mercy. Chiarelli signed old friend and UFA Milan Lucic to a seven-year (!!!), $42M contract in the summer of 2016, and the deal raised red flags almost immediately. It wasn't so much the dollar figure that caused concern, but more so that seven-year term. Lucic plays that “heavy” brand of hockey Chiarelli covets so dearly, but the problem is he’s going to be 34 when his deal expires, and he’s already too slow for the league.

Speed is the new wave in the NHL, and Lucic does not possess that skill in the least. Yes, he has other assets he brings to the table, but they’re getting less effective as the days go by based on the fact that “Looch” has a hard time keeping up with, well, any of his linemates or opponents, no matter where he plays. $6M is too much for Lucic now, so what’s it going to look like in 2022-23?

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14 Good: Philip Larsen Trade

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The first of five good moves we want to point out is a small, very inconsequential move. At the 2016 trade deadline, Chiarelli dealt Swedish defenseman Philip Larsen to Vancouver for a 5th-round pick. The pick eventually made its way to Arizona, so the Oilers never even used it to select anyone, but nonetheless Chiarelli got an asset here for a player who is not of NHL caliber, so that’s a win.

The very fact that this trade makes the top-five list of Chia moves really goes to show how ineffective he’s been. I mean, I was tasked with coming up with five good moves that Chia made during his now 2.5-year tenure as Oilers GM, and this trade made the top five. A trade that had zero effect on the roster. Incredible.

13 Bad: Leon Draisaitl Contract

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Leon Draisaitl is a phenomenal hockey player, and Oilers fans should be happy that he’s inked long term in Oil Country with an eight-year, $68M deal. Draisaitl will be the Oilers' number two center for the next decade or so, giving the Oilers an incredible one-two punch up the middle. With that in mind, the dollars on that contract are simply too high, even for a player of Draisaitl’s caliber.

All it takes is a quick look at other contracts around the league... Vladimir Tarasenko would be a generous comparison for Draisaitl, and his cap hit is still a full $1M lower than Leon’s. If you want to make the argument that Tarasenko’s contract was signed two years ago, fine then, let’s look at a more recent (and more balanced) comparison in Boston’s David Pastrnak. He’s making almost a full $2M less than Draisaitl per season. Is Don Sweeney a better negotiator than Chiarelli? Using these contracts, I’d say it’s a definitive yes.

12 Bad: Justin Schultz Trade

Kim Klement-USA TODAY Sports

I have a hard time dumping on Chiarelli for this trade, as Justin Schultz was probably never going to work out in Edmonton. Sure, Todd McLellan could have maybe tried to deploy him differently (he was constantly played as a number one D-man in Edmonton, in way over his head), but overall it’s not a stretch to say that Schultz had probably soured on Edmonton under the intense media scrutiny.

Other NHL teams—great ones, at that—recognized that there was a useful NHL player somewhere in Schultz, and the Pittsburgh Penguins ended up sending a 3rd-round pick to Edmonton for the defenseman. Schultz turned his game around almost immediately upon his arrival in Pennsylvania, partially due to proper deployment and perhaps partly due to a fresh start. He’s now a two-time Stanley Cup champion.

11 Good: Zack Kassian Trade

Timothy T. Ludwig-USA TODAY Sports

Zack Kassian has had a rough start to the 2017-18 campaign, and at the time of writing has scored only two goals this season. That said, he’s been a pretty good reclamation project for Peter Chiarelli since he was acquired from Montreal for Ben Scrivens in December 2015. Kassian had recently completed a 90-day NHL-mandated rehab stint and was looking for a fresh start, which Chiarelli offered.

Kassian notably had a few dominant games in the 2017 postseason for Edmonton, and he has quickly become a fan favorite in Northern Alberta. Sure, this season hasn’t gone the way Kassian envisioned, but not a lot has gone right in Edmonton and Kassian’s offensive struggles are low on the list of issues. The fact that Chiarelli turned Scrivens (a KHL star and possibly Canadian Olympian in a few months) into Kassian can only mean a win.

10 Bad: Benoit Pouliot Buyout

Perry Nelson-USA TODAY Sports

Alright, no more Mr. Nice Guy. This is where we really start to see Chiarelli’s errors, and this past summer’s buyout of Benoit Pouliot is inexcusable, really. Pouliot was coming off of his worst season as an Oiler, and his trade value was non-existent. Chiarelli decided the Oilers were better off paying Pouliot to leave rather than letting him hang around one more season to see if he could bounce back.

This was a very poor decision on many levels. First off, Pouliot’s underlying numbers were strong, meaning a bounce-back season was likely (he has seven goals through the first quarter of the 2017-18 season, so yeah). More importantly, the buyout means Pouliot will cost the Oilers' cap $1.33M per season through 2020-21. Had the Oilers simply waited until next summer to buy out Pouliot (when they might actually need the cap space, unlike this season), he would have been off the books one season earlier. It doesn’t make sense in any way.

9 Bad: Kris Russell Extension

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This signing is truly mind-boggling. The Oilers initially signed Kris Russell to a one-year deal prior to 2016-17 worth $3M. This was during the 11th hour of the offseason, meaning teams weren’t climbing over each other to get to Russell, to say the least. Russell had a decent campaign with the Oilers, but let’s not kid ourselves here; he is a solid bottom-pairing defenseman and nothing more. All stats—analytical, traditional, and everything in between—back this up.

Furthermore, after the Oilers second round playoff defeat to Anaheim last May, Chiarelli publicly identified that the Oilers needed to improve on defense, which we all agreed with. Rather than, you know, going out to find legitimate improvements, he stuck with the same group and doubled-down on Russell, inking the polarizing defender to a four-year, $16M deal. In a way, this contract means Edmonton is stuck playing Russell on the second-pairing (or at least paying him as such) for the duration of the deal, and that’s simply not good.

8 Good: Kailer Yamamoto Draft Pick

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Credit where it’s due, it looks as though Chiarelli struck gold with the 2017 22nd overall pick Kailer Yamamoto. Yamamoto is tiny in stature, listed as 5-foot-8 and 154 lbs. (I do believe those measurements are in skates and full equipment, too.) Small players tend to fall in the draft, but Chia decided to take Yamamoto at 22. He earned a nine-game stint with Edmonton out of training camp, and frankly speaking he’s been the club’s best RW to date, discounting Neon Leon’s time spent there, as he’s supposed to play center.

Oilers fans have to be happy with this pick, and honestly I was a little surprised that Chiarelli went with him here. The Oilers GM is infamous for valuing “heavy hockey” players, which I’m starting to believe means big and slow. He went with skill over size here, and I think it’s fair to say he should apply that ideology more consistently.

7 Bad: Brandon Davidson Trade

Billy Hurst-USA TODAY Sports

Another seemingly small move here, but nonetheless I’d say the Oilers were clear losers in this deal. At last season’s trade deadline Chiarelli sent defenseman Brandon Davidson to Montreal for David Desharnais. This was a rental, and Desharnais did score a pretty big OT goal against the Sharks in the playoffs.

Davidson is basically a less-expensive, younger, superior Kris Russell. With the Oilers suddenly embarrassingly shallow on defense again, the club elected to claim Davidson off waivers from Montreal, hinting that perhaps Chiarelli had some regret in trading Davidson last year. One would think he’ll fair better in a second-pairing role than both Russell and Matt Benning, which is the current situation in Edmonton with the Andrej Sekera injury.

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5 Bad: Taylor Hall Trade

Perry Nelson-USA TODAY Sports

The fact that Chiarelli traded Taylor Hall to fix the D, only for the defense to be a catastrophe really is impressive. Hall is legitimately one of the top-five LW in the entire NHL, and Chiarelli traded him for Adam Larsson—a good defenseman, but is probably in over his head in a top-pairing role. Side-bar: by blasting Chiarelli for this trade I am not crapping on Larsson. It’s possible to both like Larsson yet hate the trade.

The Oilers had a stellar season last year while the Devils struggled, leading a group of blowhard Oilers fans to boast that this was in fact a good trade. When I’d argue that statement, they’d say something like “look at the standings! Where’s Hall’s team? Where’s Larsson’s? Case closed.” Just curious: with the Oilers wallowing in the league’s cellar and NJ holding their own in the ultra-competitive Metropolitan Division, does that argument still apply?

4 Good: Patrick Maroon Trade

Perry Nelson-USA TODAY Sports

We’ve already said how much Chiarelli likes his heavy hockey, and the acquisition of Patrick Maroon is more evidence of that. The Oilers got bigger with the addition of Maroon, but they also got a fairly decent goal scorer too, which was a pleasant surprise to many fans and surely even Chiarelli himself.

There are several reasons this was a dynamite move by Chiarelli. Number one, Maroon has been a goal scoring machine ever since coming to Edmonton, averaging a goal every three games with the club so far. Number two, the price to acquire him was paltry—failed prospect Martin Gernat and a 4th-round pick. What’s more, though, is Anaheim is also still paying one-quarter of Maroon’s salary. A steal by Peter Chiarelli, really.

3 Bad: Jordan Eberle Trade

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Jordan Eberle has been a consistent top-line producer for his entire career. Sure, he’s prone to stretches of ineffectiveness, but when it’s all said and done, he finishes every season with somewhere between 20-30 goals and 50-65 points. These players don’t grow on trees, and hold a lot of value across the league.

Eberle had the worst offensive year of his career (rookie season not included) in 2016-17, finishing with 20 goals and 51 points. He added insult to injury by scoring zero goals and just two assists in 13 postseason games. Fans and media were not thrilled with this performance. Neither was Peter Chiarelli, apparently, so he traded away his consistent top-line winger for a crappy third line center. Now, he’s reportedly regretting that decision (duh). At least with the Hall trade they got a somewhat good player in return. The return on Eberle here is flabbergasting.

2 Bad: Griffin Reinhart Trade

Perry Nelson-USA TODAY Sports

Here we have it, the worst deal made by Peter Chiarelli as GM of the Edmonton Oilers. Shortly after taking over from MacT, Chiarelli dealt the 16th and 33rd overall picks from the 2015 draft to the Islanders for defenseman Griffin Reinhart. The 2015 draft year was supposedly the deepest since 2003, so needless to say both of those picks had high value.

I get making a trade that mortgages the future if it makes you better in the present, but that’s just the problem here. The Oilers got Reinhart in return for these two valuable assets, who had only played eight NHL games at the time. Nobody could say if they were competent NHL players at that point, let alone a good one. They’ve since, of course, lost Reinhart to the expansion draft (he's in the AHL), but the reason this deal qualifies as THE WORST move by Chiarelli is the 16th overall pick, Mathew Barzal. You know, the rookie who is averaging nearly a point a game this season and leads the rookie scoring race?

1 Good: Cam Talbot Trade

Bob DeChiara-USA TODAY Sports

Since this article was predominantly me taking a big dump all over Chiarelli, I thought it only fair to end it on a high note. When it comes to Chiarelli’s Oilers, hands-down the best trade he made was when he acquired goaltender Cam Talbot for three draft picks in 2015 (2nd, 3rd, and 7th round). Talbot had been playing second-fiddle to Henrik Lundqvist, but had definitely shown signs he’s capable of more.

Chiarelli was validated by his gamble on Talbot, who had an incredible campaign in 2016-17, playing more games (73) than any other goalie by a lot. He’s stumbled a bit in 2017-18, but so has the whole team and the ills of the Oil can’t be pinned on him. He’s simply a legit starter in a bit of a funk, and to get that piece for just draft picks was a savvy deal made by Chia.

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Peter Chiarelli’s Oilers: The 10 Worst (And 5 Best) Moves He’s Made As Edmonton GM