Here are the worst trades that Peter Chiarelli made while with the Edmonton Oilers.
Peter Chiarelli still has his fingerprints all over the Edmonton Oilers roster. Zack Kassian was only traded last off-season and while a couple of his draft picks - Stuart Skinner, Vincent Desharnais and Markus Niemelainen all played NHL games last season.
Chiarelli's draft record was miles better than his success rate for trades. Here is a list of Chiarelli's worst trades while being the general manager of the Oilers.
This trade was not that impactful as far as the on-ice product of the Oilers was concerned. Drake Caggulia was a bottom-six forward who would jump onto the top line with Connor McDavid to mix things up. Neither he nor Jason Garrison were game-breaking talent.
Related: Oilers 2023 Off-Season Guide
The real crime here was acquiring someone who injured McDavid. Brandon Manning was the defenceman who caused McDavid's collarbone injury during his rookie season. McDavid missed 37 games because of it. McDavid also spoke to the press after a loss to the Philidelphia Flyers a year after his injury and claims that Manning boasted about injuring him on that play.
This trade was one of many in the Jordan Eberle trade tree. Ryan Strome had worked himself into a third line center role. Chiarelli's time with the team was drawing closer to an end. Seemingly, out of desperation, he made this trade. Strome was well liked and other than sharing a first name with him, Ryan Spooner wasn't a noticeable player for the Oilers.
Of all of the goalies that Chiarelli could have brought in, his choice to try and give the team some depth and have NHL calibre talent was...Al Montoya. He played nine games in the 2017-18 season for the Oilers after the trade. Since those nine games, he's never played in the NHL again. The following year he played 11 games with the Bakersfield Condors with an incredibly mediocre 3.09 goals against average and a .879 save percentage.
Mark Letestu was a great teammate and mentor to the young players on the Oilers team. He should have been traded for a 3rd round pick. Instead the Oilers received a depth forward in Pontus Aberg.
Aberg skated in 16 games for the Oilers posting eight points. At least he produced to some degree, but the weight of being sellers instead of buyers at the trade deadline would stick around for another season.
Some fans may consider this to be Chiarelli's worst trade. I would argue that it is not for one simple reason - Chiarelli actually got something in the ballpark of value for the player. It was still a big drop off in value, but not as big a drop off as the two trades that follow this one.
Adam Larsson was a great defender for the Oilers. If he wasn't the return for prime Taylor Hall, the conversation surrounding him would be a lot different. He had a huge impact on and off the ice for the team. He was one half of one of the best Oilers defence pairings alongside Oscar Klefbom.
Jordan Eberle was one of the team's best players in his time with the organization. He was a mainstay in the top-six. His departure made little sense to most. There was a clear drop off in value and production between the two players, further solidified by the Oilers' coaching staff and their stubborn refusal to play Strome on McDavid's wing.
This was an absolutely brutal trade. Griffin Reinhart wasn't anywhere near being a top-four defenceman at the time, yet Chiarelli traded away a couple high value picks as if he was. He had played eight games for the Islanders averaging just over 14 minutes a night before being traded to the Oilers. That time on ice would jump up to 18 minutes over the 29 games he would play for the Oilers.
The New York Islanders then used the first round pick to draft Mathew Barzal and the 2nd round pick was traded to acquire two additional picks. The 2nd round pick was 33rd overall. Here are a few of the names selected after 33 who were drafted in the 2nd round that year: Roope Hintz, Vince Dunn, Oliver Kylington, Brandon Carlo and Rasmus Andersson.