As Peter Chiarelli and his staff search for scoring around the National Hockey League, I can’t help but shake my head. How does the organization still have enough faith Chiarelli to allow him to make a significant deal?

As TSN’s Ryan Rishaug tweeted early on Monday it seems as though the Oilers are not only aggressively pursuing a forward but are also willing to part with some valuable assets.

So as we all wait for the ball to drop on another Chiarelli deal I’ve decided to give you a look at the five worst deals he has made so far. Once again the management team that pulled the trigger on these five deals is going to be allowed to make at least one more significant change.

To Edmonton: Griffin Reinhart
To New York: 16th & 33rd overall picks

If a GM was ever going to be fired after making one trade this deal could have very much been the one. There aren’t many trades in the history of the National Hockey League where you immediately identify one team being fleeced, but this certainly fits the bill.

Chiarelli deserves to take the heat for pulling the trigger on this deal but anyone within the organization who told him Reinhart was a good pick up needs to take the blame as well.

I don’t even care who the Oilers were or weren’t going to pick this was embarrassing from the beginning. I know everyone talks about Barzal but the real story is that the Oilers were also going to take Joel Eriksson Ek over the likes of Kyle Connor, Thomas Chabot and Brock Boeser.

To Edmonton: Brandon Manning
To Chicago: Drake Caggiula

Clearly, this deal isn’t as impactful of a few other moves on the list but it’s so mind boggling I had to put it at number two.

A team full of 5-7 defensemen that is desperate for scoring trades their 5th leading goal scorer for at best a 7th d-man. This deal will never, ever, ever make sense. Even with some of the bigger deals, you can understand what Chiarelli was hoping to accomplish but this trade will never make sense to anyone. Drake Caggiula, who was sent to Chicago, summed it up best, “There were a lot of defencemen in Edmonton already and I thought they might want to bring in another forward but I’m not the one making the decisions.”

In the end, this deal won’t end up making a long-term impact on the club but that doesn’t mean it’s not troubling to see a General Manager do the exact opposite of what the team needs.

To Edmonton: Ryan Strome
To New York: Jordan Eberle

To Edmonton: Ryan Spooner
To New York: Ryan Strome

I absolutely have to tie these two deals together as Chiarelli somehow managed to lose a deal involving Ryan Strome twice.

Eberle was coming off a playoff campaign in which he scored failed to score in 13 games but the main focus of this move was to save some cap space. The issue for Chiarelli is that he never did anything significant with the added wiggle room not to mention he had enough space to keep Eberle for at least another season anyway.

Strome would play 100 games with the Oilers before Chiarelli traded him for Ryan Spooner, hoping to replace the very offence the team lost when they moved Eberle.

To Edmonton: Adam Larsson
To New Jersey: Taylor Hall

I know I’m in the minority but I still don’t hate this deal, however, that doesn’t mean it wasn’t a loss for Chiarelli. After completely blowing it on the Reinhart deal he found himself still desperate to land a defenseman.

Taylor Hall would have never won a Hart Trophy here in Edmonton riding shotgun with Connor McDavid but that doesn’t mean you can’t be frustrated watching him win the award with the Devils last season.

Adam Larsson is a good NHL defenseman and has become an important piece of the Oilers but he still should have come with another player or draft pick. I still wonder how much Chiarelli shopped Taylor Hall before deciding Larsson was the best return he could get.

To Edmonton: 91st overall pick in the 2016 NHL Draft
To Pittsburgh: Justin Schultz

The Oilers have been looking for a d-man like Justin Schultz since the moment they traded Justin Schultz. I understand things weren’t going well for Schultz but to simply give up on him for a mid-round draft pick when you literally had nothing else on the blueline was horrible, and I mean horrible asset management.

Schultz had two 30 points seasons under his belt and did not have a chance to play a full season on the power play with Connor McDavid before being moved.

In his first season after the trade, the once coveted college free agent put up 51 points with the Stanley Cup Champion Penguins

When you look at the deals above how can you possibly have any faith in Chiarelli not screwing up again? If the Oilers come out on the wrong end of another significant deal they have no one to blame but themselves, yet again. Be afraid, be very afraid.