On April 24th, 2015 the Edmonton Oilers announced they hired former Boston Bruins general manager Peter Chiarelli. Considering Chiarelli was fired by the Bruins just a few months prior, the Oilers likely should have explored more options. As we know that is not at all what happened, and not long after he was hired Chiarelli's destruction of the Oilers begun.
The first trade Chiarelli made was arguably the worst. Of course the Taylor Hall trade was brutal, but when you look deep into the Griffin Reinhart trade it's evident they're fairly equal when it comes to the lack of thought put into them. The trade consisted of a first round pick in 2015 and a second round pick in 2015 sent to the New York Islanders for defensemen Griffin Reinhart, a player who was believed to be a bust even before the trade was made. It didn't take long for Reinhart to be sent to the Oilers AHL team, and while Reinhart was on the demise, those they could have had began to rise.
The first round pick was used to draft Mathew Barzal, a Canadian centre who later had 85 points in 82 games in his first NHL season. As if that isn't bad enough, using the second-round pick the Tampa Bay Lightning (VIA NYI) drafted forward Mitchell Stephens, another centre who is currently developing nicely in the AHL with the Syracuse Crunch. Just in this one trade, the Oilers traded away a promising prospect and a franchise centre who would have been dangerously scary with McDavid and made each others statistics skyrocket. Even if the Oilers only gave up a second-round pick for Reinhart, they still would have lost the trade (See below.)
Mitchell Stephens
Griffin Reinhart
The other worst trade of his career with the Oilers would obviously be the Taylor Hall trade, which happened on July 296h, 2016. For those who don't know, on that date the Oilers traded their 2010 first overall pick to the New Jersey Devils for second pair defensemen Adam Larsson. The imbalance of value in this trade was and still is incredibly painful, especially for Oilers fans. As if it couldn't get any worse, Taylor literally cried during an interview when he was traded, meaning he had zero interest in being anywheres but Edmonton. Hall, Nugent-Hopkins and Eberble all had great chemistry, were great buds and were all three Canadian. The Oilers needed a right-shot defensemen, but this trade was nowhere near equal in value, and shouldn't have even included Hall in the first place. Even though Hall should have never even been considered being traded, if they did they should have got way more in return.
A year or so ago the Bruins gave up a first round pick, Ryan Spooner, Matt Beleskey and prospect Ryan Lindgren for (then) thirty-three year old Rick Nash. There's no questioning Nash is an incredible player, but he started producing less as one can see the last few years before he was traded. He's producing basically less than half a point per game in the last three seasons before the Bruins traded for him, whereas in comparison it's evident Hall is producing magnificently well over half a point per game (and is almost ten years younger, not even in his prime, etc) before he's traded to the Devils (see below.)
Rick Nash
Taylor Hall
Jordan Eberle
Ryan Strome
It continues to get worse, somehow.
Many of the Oilers contracts Chiarelli dealt made zero sense; most were way too long and way too big for players who were obviously getting older, slower, and overall just producing less. These are just three of the worst contracts he dealt, limiting the Oilers flexibility with their cap space by a lot.
Milan Lucic (12 points in 50 games)
Andrej Sekera (8 points in 39 games in 2018, currently injured)
Kris Russell (9 points in 40 games)
There are too many things Chiarelli should have done differently, as one can see. Here's a look at what the Oilers could have looked like if he had the skill of someone such as Steve Yzerman (assuming they drafted Barzal with the pick and that they would have a lot more cap space from not signing fourth liners and third pairings to 4-6 million dollar contracts):
F:
Hall-McDavid-Draisaitl
RNH-Barzal-Eberle
Caggiula-Chiasson-Puljujarvi
Yamamoto-Khaira-Benson
D:
Klefbom-Nurse
Bouchard-Sekera
Benning-Bear
G:
Talbot
Koskinen
Scratches: Kassian, Jones, Russell,
On the bright side, Oilers fans can always try out the lineups in Franchise Mode on NHL 19.