Edmonton Oilers: Looking back at Peter Chiarelli’s worst moves

Peter Chiarelli ruined the Edmonton Oilers. Let’s look back at his worst moves.

Despite the Edmonton Oilers being the worst team in the league for an entire decade, the majority of them would give you the same name if you asked them who the most hated man in the city is. That name is Peter Chiarelli.

After finishing near the bottom of the standings in every single season since their cup run in 2005-06, the Oilers decided to hire in the spring of 2015 after he was fired by the Boston Bruins. This move brought excitement to the city as it appeared the team had finally gotten rid of the ‘Old Boys Club’ and instead brought in a guy who had helped construct the 2011 Stanley Cup winning Boston Bruins.

Just a few months later, the Oilers selected Connor McDavid at the 2015 NHL Entry Draft, and it appeared that they were destined for greatness after a very tough stretch.

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The first year with Chiarelli in charge was a tough one as McDavid missed half the season due to injury and the team was yet again near the bottom in the standings. However, the very next season things turned around big time. By the end of the 2016-17 season, the Oilers found themselves finishing second in the Pacific Division with 103 points.

This marked the first time the team had been in 11 years. Chiarelli was thought of as one of the big reasons the team was able to turn things around, and he was even one of the final three nominees for general manager of the year.

Unfortunately, things went downhill very quickly after that. The team missed the playoffs in 2017-18, and were struggling big time in 2018-19, which led to the firing of Chiarelli in January of that season. Though it was a quick fall from grace, it wasn’t a surprising one as he had made many questionable decisions that almost all turned out to be bad if not outright disasters. Here is a look at some of the worst moves he made during his tenure with the Oilers.

Koskinen Contract

The first season Mikko Koskinen came over to the Oilers, he was very unknown. The 6-foot7 goaltender hadn’t seen any NHL action in nearly a decade, but had posted intriguing numbers in the KHL. His one-year, $2.5 million contract ended up being a good bet by Chiarelli as he outplayed Cam Talbot and was having himself a decent year.

However, he was already 30-years-old, and while he had played solid in his short stint with the Oilers it certainly hadn’t been spectacular. That’s what made the decision to sign him to a three-year, $13.5 million extension so baffling. There was no reason to make this signing at the time as Koskinen had yet to prove himself and there was still plenty of time left in the season.

Fast forward to this season and it is much the same with the big Finnish netminder. He is a good goalie, however he isn’t consistent enough on a night to night basis to warrant a contract that pays him $4.5 million per season.

One other factor that made this signing so strange was that Chiarelli was fired by the Oilers just days later, yet it was claimed by Bob Nicholson, the teams Chairman, that the firing had nothing to do with the Koskinen deal.

Caggiula/Manning Trade

One of Chiarelli’s biggest pani’ moves came when he traded forward Drake Caggiula along with defenseman Jason Garrison to the Chicago Blackhawks for defenseman Brandon Manning and then prospect Robin Norell.

Now make no mistake, Caggiula is an average at best bottom six forward and Garrison was not an NHL level player anymore. The reason it made no sense was because neither was Manning.

The reason I consider it a panic move is because fans were growing more and more impatient of the teams struggles and Chiarelli seemed to react instantly rather than think this move through.

At the time, Manning was on a deal that was paying him $2.25 million per season and still had another year left on it, which was a bigger cap hit than Caggiula and Garrison combined. Considering the Oilers were already a team with almost no cap space and had zero forward depth, this move made no sense from the second it was made.

Of course, this deal only made Oilers fans more frustrated with Chiarelli. Not only did the move not make sense from a hockey perspective, but also from the sense that McDavid, the teams captain, had a very well documented feud with Manning. Non-surprisingly, this move never worked out, as Manning was sent down to the AHL not long after he was acquired, and spent the majority of the 2019-20 season there as well.

Strome/Spooner Trade

The Ryan Strome for Ryan Spooner trade was the other move that appeared to be made out of panic. At the time of this trade, Strome was in his second season with the Oilers. Sure, he had been struggling mightily offensively at the time, but he was still playing sound defensively and had a much higher ceiling than Spooner.

While Spooner’s NHL career appears to be over, Strome’s is really beginning to take off. The former fifth overall pick was in the midst of a career season for the Rangers, with 18 goals and 59 points in 70 games.

At just 26 years old, he appears to have truly arrived at the NHL level and will likely be a good player for the Rangers for years to come. Though the Oilers were a much better team in 2019-20, they still lack secondary scoring and Strome would be a very important player for them had he not been traded.

Eberle/Strome Trade

As bad as the Strome for Spooner trade was, the Jordan Eberle for Strome trade a year and a half prior was even worse. The fact Eberle was traded in the summer of 2017 came as no surprise. It was becoming clear the team was beginning to run into salary cap issues, and he had struggled in the team’s playoff run just a few months prior.

However, he was at the time the teams best scoring winger, and could be counted on for around 25 goals and 55-60 points a season, while Strome had only one fifty-point season under his belt at the time.

The one thing that did make sense about this trade was that it gave the Oilers $3.5 million in cap space, as Eberle was on a deal paying him $6 million annually while Strome was at just $2.5 million. Everyone assumed that with this cap space the Oilers would add more in order to build off of the previous season’s playoff run and hopefully go even further in 2017-18.

For some reason, that never ended up happening. Chiarelli ended up using the cap space on nothing, even as the team struggled. As a result, they took a major step backwards that season, missing the playoffs once again.

As of today, Eberle is still a member of the New York Islanders. Though his numbers aren’t what they were with the Oilers, they are in a system with Barry Trotz that teaches defensive play, and as a result many players numbers decrease while playing for him. Regardless, it appears they are happy with Eberle’s play as they gave him a five-year extension worth $5.5 million per season.

Hall/Larsson Trade

Out of all the trades Chiarelli made as the Oilers gm, this one was by far the most controversial. Immediately this trade was criticized by all members of the media, as they all mentioned Hall had much more value than Larsson. This was true at the time, and is still true to this day.

The unfortunate thing about this trade is that Larsson is a good defenceman, but often gets criticized simply due to the fact he was involved in a very lopsided trade, which isn’t his fault. For the most part, he has been quite solid in Edmonton in a top four role, and is an important part of their team. Despite that, this was a very poor trade.

As mentioned a few times previously, the Oilers lack offensive production from anyone other than McDavid, Draisaitl, and Nugent-Hopkins. Hall is one of the most dynamic wingers in the game, and proved that during the 2017-18 season when he put up a career high 93 points and was awarded the Hart Trophy.

Fast forward to where we are now, and this is still seen as a very lopsided trade. In fact, it is so uneven that it alone could be a firing offence for general managers around the league. For Chiarelli however, he was able to keep his job for a long while after, and shockingly, he ended up making an even worse trade.

Lucic Contract

Shortly after trading Taylor Hall to the New Jersey Devils, Chiarelli signed power forward Milan Lucic to a seven-year, $42 million contract that paid and continues to pay him $6 million annually. Though Lucic had been a dominant NHL forward for quite some time, many questioned this deal as the league was appearing to transition to a smaller, quicker, and skilled game. Sure enough, the pundits turned out to be correct and this contract turned out to be a complete disaster.

While the first season, 2016-17, went well for Lucic with 50 points, the next two were complete disasters. The 2018-19 season was by far the worst statistical season of Lucic’s career, as he was only able to put up six goals and 14 assists despite playing 79 games. Meanwhile, Hall, who Chiarelli ultimately replaced with Lucic, was putting up points at a very high rate.

This past offseason, the Oilers announced the hiring of general manager Ken Holland. He didn’t waste any time, as he quickly offloaded Lucic and his contract to the Calgary Flames in exchange for James Neal. The change in scenery didn’t appear to help the former Boston Bruin out, as he finished this season with yet again 20 points. Unfortunately for the Flames, this deal still has three more seasons remaining.

Reinhart Trade

While I did consider putting the Lucic signing at number one, the bottom line is he was a positive factor for the Oilers during his first season, and was still able to make small contributions over the next two seasons. The same cannot be said for defenceman Griffin Reinhart, who only played 29 games for the Oilers.

That’s what made the Oilers trading both their 16th and 33rd overall draft picks at the 2015 draft so disappointing. This trade, which was the worst Chiarelli made during his time with the Oilers, was made just two months after he was hired.

It should have been a warning sign for Chiarelli that the Islanders were willing to move on from Reinhart, who they selected fourth overall at the 2012 draft, so quickly. Clearly, they had figured out that the game was transitioning away from the bigger, slower players.

Chiarelli however, did not realize this at the time and ended up gifting the Islanders with two high picks in a very deep draft. What makes this trade sting so much more is the fact that the Islanders selected superstar Mat Barzal with the 16th pick.

Now, as mentioned, Barzal is a superstar in the NHL, and is only 23-years-old. Reinhart on the other hand hasn’t played in the NHL for four years, and just finished up his first season in the KHL. Though he is just 26-years-old, it seems unlikely he will find his way back to the NHL.

This list goes to show just how bad of a job Chiarelli did with the Oilers. Despite coming in with a good resume, it is likely his time spent with the Oilers ruined any chance of him getting another shot as an NHL general manager.

Many of these moves could be put on a list for the worst moves of any NHL gm over the last 10+ years, yet they were all made by the same guy. Somehow, despite being given a roster with the likes of McDavid and Draisaitl, Chiarelli was not only unable to turn the Oilers into a cup contender, but set them back years and years.