SOH Top 10: Worst Peter Chiarelli Decisions


Photo by Shaughn Butts

If there is one thing that Covid-19 is giving me a chance to do, it is reminisce.  They aren’t all going to be fond memories, but sometimes it’s fun to even look back at the bad times and laugh…no matter how fresh that wound still is for some.  And for Oilers fans, who I consider myself one of, the Peter Chiarelli era will be viewed as the absolute worst for several reasons.  Many in Edmonton believed that this was the turning point for the franchise, when in fact they hit an all-new low for incompetence under his watch.  This man was gifted McDavid, Draisaitl, Hall, Nugent-Hopkins, Eberle, Klefbom, Nurse, the 16th pick in what will likely be a top-five draft of all-time, and a mountain of cap space.  Given that, it is likely the worst job a GM has ever done in the history of the league.  Yes, worse than Mike Milbury.


I changed the title of this from “trades” to “decisions”, even though you can come up with 10 awful trades the man made.  For a top 10 list to truly be interesting, you need a little controversy and to have some solid candidates not make the list.  So without further adieu, here is the list (I know Oilers fans, you want to read it while peaking out of your covered eyes, but remember that we aren’t supposed to be touching our faces these days).


Hounourable Mention

June 22, 2017: Jordan Eberle for Ryan Strome

This one gets honourable mention because the Edmonton media (specifically Mark Spector) remember it as this horrendous decision,  but it was actually one of his better moves.  Initially, Eberle had a great bounce-back season with the Islanders, and Strome wasn’t great for the Oilers.  But since the trade, Strome has nearly matched Eberle in goals (60-56) and points (137-129) for half the money.  Yes, one problem is that Strome didn’t get it going until he went to the Rangers, but even with the Oilers he had 19 goals his first season (35 points) and had terrific analytic numbers early in the 18-19 season, it was just simply a case of not getting bounces to that point.


June 29th, 2017: Benoit Pouliot Buyout (4 years, 1.3 million cap hit per season)

This was the straw that broke Soups back…or something like that.  I texted one of my buddies after this and flat out said: “I’m done with this fuck” or something to that effect.  He did nothing with the savings (Jussi Jokinen could have been signed without the buyout).  But that aside, Pouliot was still capable of being a top-nine forward and even if he had gone to shit during that season you could have simply put him on waivers and buy him out after that season, which would have saved you a year on the buyout.  AKA, the Pouliot buyout wouldn’t still be on the books this upcoming off-season.  Sure would be nice to have an extra 1.3 million…


August 16, 2017: Leon Draisaitl signing, 8 years, 68 million (8.5 million cap hit per season)

YEP!  This at least gets an honourable mention.  One of the best bargain contracts in the NHL at this moment still gets a shoutout.  How in the hell does that happen?!  I’m certain you’re asking that question.  It is pretty damn easy for me why.  As good as that contract currently is, it was still easily…EASILY…a million per season of an overpay by Chiarelli, and it can be argued that it’s as much as 1.5 million per season.  Look at that date too.  Chiarelli wasn’t close to a pressure point yet of needing to get Draisaitl signed and get him into camp.


January 4, 2018: 4th round (conditional) pick in 2018 NHL Draft for Al Montoya

He traded a conditional 5th round pick, which with ease turned into a 4th, for a backup goaltender.  Ok, that’s not so bad.  Cam Talbot desperately needed someone who could take starts from him at the time.  So why was this such a bad decision?  Oh, because when the trigger was finally pulled on this deal, the Edmonton Oilers were out of the race for the 2018 post-season.  They so obviously, and desperately needed a backup that Todd McLellan would trust and play from the start of the season.  McLellan showed zero faith in Laurent Brossoit and in turn, Laurent Brossoit was awful playing for Todd McLellan.  A good GM would recognize this very early in the season and address the issue, but as we know Peter Chiarelli was far from a good GM…


10. February 18, 2011: Blake Wheeler and Mark Stuart for Rich Peverley and Boris Valabik

While there are four players in this deal, the main parts were Wheeler and Peverley.  This was the first of his questionable decisions, back when we all believed he was pretty competent.  But even at the time, I remember thinking “Wheeler was awesome as a rookie for them, why would they give up on him for a guy like Peverly?!”  Not that Rich Peverley was NOTHING, but he sure wasn’t a big addition to that Bruins team.  Some would say “well it worked because the Bruins won the Cup”.  Yeah…something tells me that they could have won the Cup with Wheeler instead of Peverley…


9. June 21, 2018: Eric Gryba Buyout (2 years, 300K cap hit per season)

WHAT……….IN THE BLOODY FUCK……….WAS……….THE FUCKING………. POINT……….?  Chiarelli here decides that while he is already up against the cap to push his team even further against the cap by buying out Eric Gryba who would have been $0.00 against the cap by simply spending the season in the AHL.  It was 300K against the cap and I very vividly recall Bob Stauffer laughing on air one day that some people were upset about this.  Sure, it’s not much of a dent in the cap.  But there are two things: A) it further showed the incompetence of Chiarelli, and B) they were so tight to the cap that they shouldn’t have been doing something they didn’t have to like putting 300K towards it when they don’t have to.  This decision doesn’t rank high (if at all) in terms of impact, but the sheer stupidity of it is off the charts!


8. June 23, 2018: 5th Round pick for Hayden Hawkey

This one flew under the radar for most people, but it sure drew my ire!  He moved a 5th round pick for a goaltender entering his senior season in college and then didn’t sign him.  WHAT?!?!  So you blindly gave up a 5th round pick, with no conditions on it at all, for a goaltender he didn’t know if he could sign, or if he’d have room on the roster for him if he did want to sign him.  Holy FUCK.  If he was so eager to get Hawkey’s rights, why wouldn’t the deal have at least been a 7th that turns into a 5th if they sign him?!  I don’t know how much I can type the words “mind-blowing”, but we’re going to find out!


7. February 28, 2017: Brandon Davidson for David Desharnais

Do you remember the logic behind this?  “We have to move Davidson, otherwise we’ll lose him in the expansion draft”.  So, instead of losing one asset for nothing, he lost two.  It’s as though he believed that if he gave up Davidson for an asset that he was set to lose (David Desharnais) then Vegas couldn’t take another player from his organization.  Instead, he cleared the path for Vegas to take a player they had invested the equivalent of two 1st round picks in (given the quality of that draft), while also hurting the depth of the Oilers blueline, for a very minor upgrade that they likely could have acquired (or got someone similar) for a mid-round pick.  That is QUITE the logic by Pete.  I am well aware of the goal that David Desharnais scored for the Oilers in game 5 of the 2017 series vs San Jose.  I also am well aware of the fact that the ice time would have gone to another player in that spot who likely also could have scored that goal.  Desharnais outside of that solid game in game 5 (also set up the tying goal) wasn’t much of an addition for the Oilers, and when the blueline got beatdown in the next series against Anaheim they sure could have used a guy like Davidson to step in.


6. November 16, 2018: Ryan Strome for Ryan Spooner

Strome for Eberle is surprisingly sneaky good, but this is where he should be crucified.  In fairness, I thought it was actually a good move at the time.  The career numbers suggested it was a solid move, which is why perhaps I have this lower in my rankings than most would.  But this was such a disaster.  The icing on the cake was that Strome was tight with McDavid, and Spooner from everything I’ve heard (this could be wrong so don’t hold me to it) was pretty immature and not well-liked in the room.  While Strome has been a home run in Manhattan, Spooner was bought out by the Canucks after the 18-19 season and played this past season in Europe (and didn’t even stick with one team or even one league over there).


5. December 30, 2018: Drake Caggiula and Jason Garrison for Brandon Manning and Robin Norell

This one was more obviously worse from the get-go.  The final trade as the Oilers GM, and likely as an NHL GM.  Little Petey thought that it would be a good move to shed one of the fastest forwards on the roster, a roster which severely lacked speed, and one of his franchise players best friends on the team, for a defenceman who in no way whatsoever was a need, and was notorious for not only being the player to break Connor McDavid’s clavicle but then getting into it with McDavid the next time the two played.  To top all this off, his roster that was already rubbing up against the cap added 750K to it, and another year at 2.25 million.  That man was SOMETHING ELSE.


4. January 21, 2019: Mikko Koskinen extension

This one is very similar to the Draisaitl contract.  It’s not so bad NOW, but he drastically overpays for a player for no reason whatsoever.  Koskinen was already digressing after a hot start, and Chiarelli gave him 1.5-2 million more per season than he was worth at the time, and as we found out that value would continue to fall as the season wore on, to the point where people were openly asking whether or not the Oilers should buy him out of the deal before it begins (which they couldn’t have unless they had a player going to arbitration which opens up a 2nd buyout window after July 1st).  He didn’t just give Koskinen 4.5 per, he also added a modified no-trade clause.  Because simply just overpaying players wasn’t enough for Peter.


3. June 29, 2016: Taylor Hall for Adam Larsson

Some, maybe most, would have this higher on their list than I do.  I have always at least been able to see some logic in this one.  Don’t get me wrong, nobody in their right mind should ever have believed that this trade was worth doing one for one (as Bob McKenzie for some reason loves to constantly remind us of…I’d hate him if he weren’t the best).  They saved nearly two million in cap space, got an extra year on the deal coming back than the one going out, got a specific need, and in 2016 it looked as though Larsson was just beginning to grow as a player rather than having already maxed out.  I also did somewhat understand the logic behind “making it McDavid’s team”.  Having said all this, again I want to make it extremely clear that I wouldn’t have even given this deal a thought.  I would have done it perhaps if Jersey had kicked in a 1st round pick and another prospect (remember too, Jersey’s 1st in 2017 ended up being 1st overall).  There was a big need for the organization at the time to rebuild their system as the entire time to that point which they had been rebuilding, they still had next to nothing in the system.  But not a FREAKING CHANCE would I have even considered this one for one.  My man Pete sure did though.


2. July 4, 2013: Tyler Seguin, Rich Peverley and Ryan Button for Loui Eriksson, Joe Morrow, Reilly Smith and Matt Fraser

This is what they were willing to put on camera, who the hell knows what the real conversation was.  Just like Hall, it’s not that they dealt him.  I’m not a huge Tyler Seguin fan and wasn’t at that time so I understand their frustrations.  But it’s that they simply made up their minds on trading him rather than making sure they could get the right deal rather than simply taking the best deal.  That seems to be the pattern with Chiarelli.  He makes up his mind on a player, and if he’s made up his mind that he no longer wants the player, then he’ll just take whatever the best deal is for him.  Even if you go back to that time, I can pull out all the positives and make it sound as good as possible.  Loui Eriksson was one hell of a two way forward.  Joe Morrow was still a decent prospect.  Reilly Smith looked like he had top nine, perhaps top-six potential.  Matt Fraser was…not much.  But he got three respectable pieces.  And Seguin was not only pure trash in the 2013 playoffs, but there were also rumours EVERYWHERE that he was a complete shit show off the ice.  Having said this, you’re still giving up a 21 year old kid who not only has franchise centre potential but at times Seguin had lived up to that potential just three years into his career.  Add to that, you also move out the guy that you just traded Blake freaking Wheeler for in Rich Peverly in the deal.  So he essentially gave up Seguin and Wheeler for three average pieces.  Three pieces/players who can be signed every summer in free agency.  Even with what Eriksson was, he still wasn’t worthy of being the key piece to fetch a potential franchise centre.  It was a very bad trade at the time that got so very much worse as time went on, much like the Hall/Larsson swap.


1. June 26, 2015: 16th and 33rd overall picks in the 2015 NHL Draft for Griffin Reinhart

This is the one I tweaked about more than any other because I knew what they were giving up, and I knew the value on what they got back had greatly diminished.  It wasn’t that I had a hate on for Griffin Reinhart, but to give up the 16th and 33rd picks in a draft that was being compared to the 2003 draft (and five years after the fact it has lived up to that billing) for a prospect who was scuffling and his organization had clearly soured on him was as foolish as it gets.  Mat Barzal is the one that always gets pointed to as who they passed on, but Ilya Samsonov WOULD have made sense and SHOULD have been a target for the Oilers, Kyle Connor, Thomas Chabot, Brock Boeser, Travis Konecny was one of my favourites in that draft, even the guy who it is rumoured they would have taken…Joel Eriksson Ek would have been a much wiser play.  And when you look at Eriksson Ek, one thing you have to keep in mind is that the Minnesota Wild rushed him and messed up his development.  And even then, he seems to now be progressing.  None of the players I mentioned were guys who look good in hindsight.  They were all very serious contenders to go in that range and perfect fits for the Oilers needs at the time.  The other side of this coin that drives me nuts isn’t even that Reinhart didn’t pan out, nor is it that they lost him in the expansion draft.  The thing that drives me insane still to this day is that he was NOTHING of a need!!!  The left side of the blueline moving forward was fine!  They had two kids in Klefbom and Nurse who were progressing very nicely at that point.  Brandon Davidson was a solid prospect at that point, at least as good as Reinhart at that time.  It was mind-blowing.  Now, you might have it further down on your list because it is highly unlikely that Chiarelli had done any of the leg work to make this deal happen, and I understand that logic.  I even subscribed to it for a long time.  But he was still in charge and still greenlit the deal.  He had the power to tell the guys who were still around who believed everyone on the 12-14 Oil Kings were going to the hall of fame that they weren’t, and he didn’t.

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