It wasn’t a matter of if, but a matter of when. Chiarelli has finally been relieved of his duties as General Manager of the Edmonton Oilers and the city can breathe a long-awaited sigh of relief. For all his good intentions in trying to bring the Oilers back to their former glory, he has failed on every account. Disastrous trades, draft mistakes, inability to develop prospects, poor free agent signings and horrible cap management have dragged a team that should have been a perennial Cup contender down to the basement of the league.

Let’s review the timeline of what went wrong during Chiarelli’s tenure.

  • June 26, 2015: Chiarelli trades 1st and 2nd round draft picks for defenseman Griffin Reinhart. It had already been three years since he was drafted as a highly touted prospect, but Reinhart was not looking at all NHL ready. Why a GM would give up two valuable picks to gamble on a prospect whose stock was falling makes no sense. The gamble didn’t pay off. Reinhart is no longer with Edmonton and looks destined to be a career minor leaguer. Meanwhile that 1st round pick was used to draft Matthew Barzal. Barzal was last season’s rookie of the year and is one of the brightest young stars in the league. The 2nd round pick is Mitchell Stephens who hasn’t made the NHL yet but is looking good in the AHL.
  • January 29, 2016: Chiarelli trades left winger Taylor Hall to the New Jersey Devils in exchange for defenseman Adam Larsson. Larsson has no offensive value but has been a solid shutdown defender for the Oilers. Meanwhile Taylor Hall blossomed into an offensive juggernaut and league MVP in Jersey. Swapping an MVP for a solid stay at home defenseman is one of Chiarelli’s biggest blunders. It shocked the hockey world at the time and turned out even worse than anyone thought it would.
  • February 27, 2016: Chiarelli trades defenseman Justin Schultz to the Pittsburgh Penguins for a 3rd round draft pick.  Justin Schultz went on to have immediate success in Pittsburgh, blossoming offensively, winning back to back Stanley Cups and finishing 10th in Norris trophy voting. The Oilers didn’t do anything meaningful with the draft pick so essentially lost Schultz for nothing.
  • June 24, 2016: Chiarelli drafts Jesse Puljujärvi 4th overall. This move itself doesn’t deserve any blame. At the time Puljujärvi was the best player on the board. It just hurts that he really hasn’t developed into an NHL caliber player, meanwhile the next two forwards taken (Tkachuk and Keller) have been incredible. While drafting him was not a mistake, you have to wonder if Edmonton has made any mistakes with his development as he joins a list of other Oiler prospects who haven’t lived up to expectations.
  • July 1, 2016: Chiarelli signs left winger Milan Lucic to a 7-year, $42 million deal with a no movement clause. Lucic had a good first season in Edmonton but regressed the following year and this year has been horrible. He’s not the same player he once was and his $6 million per year is really hurting the Oilers cap situation and ability to make trades or sign other players.
  • October 7, 2016: Chiarelli signs defenseman Kris Russell to a 4-year $16 million contract. Russell is a 3rd or borderline 2nd pairing defenseman and hasn’t been great in Edmonton. $4 million per year and that kind of term on a player who hasn’t contributed much is just another move that hurts the cap situation. One bad contract alone doesn’t kill a team but when you fill a roster with big money contracts of players who don’t contribute it makes for a difficult hole to dig out of.
  • June 22, 2017:  Chiarelli trades right winger Jordan Eberle to the New York Islanders in exchange for Ryan Strome. It’s worth noting at the time and still true, Eberle’s worst career season was still better than any season Strome has ever had. After Strome failed to work out in Edmonton Chiarelli flipped him for Ryan Spooner. Two months after trading for Spooner, he was placed on waivers. So essentially Eberle, a perennial 20+ goal, 50 to 60 point player was traded for nothing.
  • June 29, 2017: Chiarelli buys out Benoit Pouliot’s contract. With 2 years left at $4 million per season this caused the Oilers to instead take a cap hit of $1.3 million for the next 4 years. Pouliot was good for the Oilers, he provided solid offense and could kill penalties. Buying him out after one down year may not have been the right move. He could be in the final year of his deal right now but instead, the Oilers have to count him against the cap for an additional two years after this one. This is pretty minor compared to these other moves, but still could have been handled differently.
  • December 30, 2018: Chiarelli trades left winger Drake Caggiula and defenseman Jason Garrison for defenseman Brandon Manning and defenseman Robin Norell. Maybe not as big as some of these other moves but this one is very confusing. None of these players are stars by any means but Caggiula is the best player involved in this deal. Why flip him for a lesser player in Manning? To add another bizarre layer Cagguila is Connor McDavid’s friend from high school while Manning famously ended McDavid’s rookie season with a dirty hit that broke his collar bone. Aside from not even being a good hockey move, what a way to piss off the dressing room and fanbase by trading a well liked player for public enemy number one.
  • January 21, 2019: He just had to get 1 more in, a day before being fired. Chiarelli signs goaltender Mikko Koskinen to a 3-year $12.5 million contract. Koskinen is 30 years old, basically has no NHL experience (played 4 games 8 years ago and 27 with Edmonton at the time of the signing) and has been solid but nothing special in this minuscule sample size of work. How is 27 games enough to decide to pay him $4.5 million per year? He hasn’t proven anything and there’s no book on him yet. He’s been pretty good, but 27 games could be a fluke, his next 27 might be terrible. Why rush, was anyone else clambering to sign an unproven goaltender to an eight-figure deal? This could be a steal of contract if Koskinen ends up being great, but right now it doesn’t make much sense.

And there you have it. Chiarelli’s tenure as General Manager of the Edmonton Oilers lasted from April 24, 2015 to January 22, 2019.  It’s been a long, strange and frustrating few years, but it’s finally over. For anyone saying the Oilers need a rebuild, they do not. As bad as they’ve been they still have core star players in McDavid, Draisaitl and Nugent-Hopkins as well as promising prospects like Yamamto, Bear and Bouchard. Nope, this isn’t a team that needs to rebuild, it’s a team that needs to retool and hopefully whoever takes the torch as GM can do that because if there’s any fanbase that deserves to see success and deserves to have fun watching their team play, it’s Edmonton. Good luck Oilers and here’s to the next GM finally being the right one.