Peter Chiarelli’s time in Edmonton began with a 2017 second-round draft pick being given to the Boston Bruins, and that was just so the Edmonton Oilers could bring him on board. That pick turned into Jack Studnicka, and though this was not Chiarelli’s fault or a move under his management, giving away a high draft pick in order to acquire a general manager was not a good start to his tenure.
Chiarelli started his stint on April 24, 2015, shortly after another playoff-less season was in the books. Two years later, he was nominated for the Jim Gregory General Manager of the Year Award, though he ultimately lost to David Poile of the Nashville Predators. That was the season in which Chiarelli assembled a squad that snapped a 10-year playoff drought, fell two points short of winning the division, and one game shy of reaching the Western Conference Final. Less than two years later, he was fired mid-season after a series of questionable decisions, and just one playoff berth to show for it.
After winning three Stanley Cups with the Detroit Red Wings, Ken Holland joined the Oilers hoping to finally turn the team around after a hard decade and a half. He was hired on May 7, 2019, before the 2019 NHL Entry Draft, and was given enough time to get himself ready to kick off his tenure with one of the most important days of the offseason.
We shall take a look at both Chiarelli and Holland’s notable signings, good and bad, while acting as general manager. We will also dive into each of their best trades, worst trades, draft steals, and draft busts.
Notable Signings, Good and Bad:
Peter Chiarelli
Milan Lucic was signed to a seven-year deal that came to $7 million average annual value (AAV). This was Chiarelli overestimating how much an older power forward was worth, and also got caught overpaying in free agency.
Chiarelli pulled the trigger on signing Leon Draisaitl at the perfect time, with his contract of $8.5 million AAV looking like a total steal for what he brings to the table as one of the best players in the world now.
As the last straw for Chiarelli before he was fired, he signed Mikko Koskinen to a three-year deal worth $4.5 million AAV before he had even played a complete season with the team — a deal that has turned out to be a bad signing, as predicted. Chiarelli was fired the next day.
In the season that Koskinen was signed to this extension, he was splitting the time with Cam Talbot who had just come off two consecutive 30-plus-win seasons for the Oilers. His lowest goals-against average (GAA) in the three seasons he’s spent with Edmonton has been 2.75. Koskinen has also only exceeded .906 save percentage (SV%) once in those three seasons as well. There have been times where he has had to assume the starter role while the other goalie has been out with an injury, but lost the starting job immediately once Mike Smith returned last season.
Ken Holland
Darnell Nurse has been signed twice under Holland’s management — the first on a two-year bridge deal, paying him $5.6 million AAV. That was a very fair deal considering he was elevated to be the top defenceman with Oscar Klefbom having injury problems. The second deal is considered very questionable, but is around the number that multiple defencemen have been signed for this offseason. Nurse was signed to an eight-year extension worth $9.25 million AAV.
Nurse is the No. 1 defenceman in Edmonton, and played his way into the Norris Trophy conversation last season. But not playing on the top power-play unit is one of the questions as to how much he is being paid. Most No. 1 defencemen on teams play in all situations, or at least top power-play minutes, as well as big minutes overall.
With Tyson Barrie signed for three more years, and Evan Bouchard rising up through the depth charts, Nurse will be stuck on the second power-play unit for the foreseeable future. What lessens the blow of that much money being paid to one defender is the physicality Nurse brings to the table, as well as his shot and defensive play. He is also a guy who can eat minutes, so he is always a presence out on the ice and allows the other defencemen to play more to their strengths.
Holland was able to bring back longtime Oiler Ryan Nugent-Hopkins on a very team-friendly deal. It’s hard enough to get players to sign in Edmonton when the team has to overpay for them, nevermind a player taking a cap hit to stay with the team. Nugent-Hopkins not only brings offense to the table, but is a stud in the defensive zone every night.
Zach Hyman is another big signing that Holland made this offseason, finally stabilizing the left wing position beside Connor McDavid. By the way Hyman plays with and without the puck, it is a fair deal right now. Down the road is yet to be seen.
What doesn’t seem like the best signing now is the extension of Zack Kassian to a four-year deal paying him $3.2 million annually. He will be fighting for his spot in the bottom six, as the top six seem to be all but set, and the bottom two lines will have competition. Kassian did put up some decent numbers, but that’s taking into consideration he was playing alongside McDavid on the top line. It is a bit of an overpayment to add physicality to the lineup when he isn’t guaranteed to play every night next season.
Jesse Puljujarvi is one player who struggled to find his game at the NHL level under Chiarelli’s management and decided to go back home to play. Then, under Holland, was able to reach a low-risk, high-reward deal that brought the former fourth-overall pick in 2016 back to the team with a fresh start. Puljujarvi’s attitude completely changed, and having a top-line talent being paid only $1.175 million for two seasons was a complete steal. This is on top of him seeing top power-play time as well as penalty-kill minutes.
Best Trades
Peter Chiarelli
On Day 2 of the 2015 NHL Entry Draft, Chiarelli did bring in a starting goalie in Talbot for cheap, considering the only draft pick that turned into anything was Jonas Siegenthaler. Edmonton got a legit starter who put up great numbers for his first three seasons. Talbot posted a 42-win season in his second year with the Oilers that also helped the team make the playoffs for the first time in 10 seasons, making it to a Game 7 in the second round.
Kassian was acquired in a trade from the Montreal Canadiens that saw Ben Scrivens go the other way. Since Chiarelli had just stolen a goalie from the New York Rangers at the draft, this presented the opportunity to add toughness up-front and send Scrivens away. The previous season saw the goaltender put up horrible numbers for a team that was in the basement of the league. Regardless, he posted a 3.16 GAA and an .890 SV%. Kassian turned out to be a huge physical force in the regular season and especially come playoff time in 2017 where he ran around the ice hitting everything. He is still in Edmonton and has shown he can play up and down the lineup, while Scrivens played his last game in North America the season after he was traded to the Canadiens.
Chiarelli seemed to pull off a steal in acquiring Pat Maroon from the Anaheim Ducks in February 2016. The Oilers sent Martin Gernat, an American Hockey League (AHL) player, and a fourth-round pick that hasn’t turned out, back to Anaheim. Maroon flourished alongside McDavid on the top line, and posted career numbers. In 2015-16, Maroon’s split between Anaheim and Edmonton was 13 points in 56 games, and then 14 points in 16 games once coming over to the Oilers. Maroon almost became a 30-goal scorer on Edmonton’s top line the next season while also posting good numbers in the playoffs.
In three separate trades, Chiarelli seemingly stocked up the goalie prospects in the minors for the Oilers, acquiring Stuart Skinner, Oliver Rodrigue, and Ilya Konovalov. Edmonton only had to give up two third-round picks, two fifth-round picks, and Brandon Davidson. Any of these three young goaltenders can make a case to be the future starter for the Oilers, and that would save other assets in building home-grown talent that can fill positional needs. None of the third-or-fifth-round selections turned out to be anything yet, so as far as I’m concerned, the Oilers won all three of those trades. Having competition to be the next guy to be called up creates a higher compete level and will hopefully push each of the goalies to the top of their games.
As of now, acquiring Cooper Marody from the Philadelphia Flyers for a third-round selection has turned out nicely. If nothing else, he was on the top scoring line in the AHL last season, which featured Ryan McLeod and Tyler Benson, two players who have a very good shot at making the opening day roster after training camp in 2021-22. We may see Marody on the Oilers some time soon with how he’s played in Bakersfield.
Ken Holland
Holland’s first deal in Edmonton saw the team acquire James Neal from the Calgary Flames for Lucic. Lucic had really been struggling after his first season in Edmonton, and Neal seemed to have dropped off after his recent years. Neal immediately found his goal-scoring touch again after arriving in Edmonton, netting 19 goals in 55 games, and solidifying his spot in front of the net on the league’s best power play.
Holland has traded all three of the defensive draft steals that Chiarelli chose in 2015; Caleb Jones, Ethan Bear, and John Marino. It is very impressive that a fourth-, fifth-, and sixth-round pick hits in the same year. One of these picks was wasted in trading away John Marino, but the other two have seen a return of Duncan Keith and Warren Foegele. Both players fit a role that Edmonton was in need of — an experienced veteran defender in Keith who still has gas left in the tank, and a very solid third-line player who has proven he can put up points in a depth role.
Worst Trades
Peter Chiarelli
Chiarelli’s time in Edmonton did not start off well, and looks even worse now. On Day 1 of the 2015 NHL Entry Draft, he sent a mid first-round pick in 2015 (16th overall) and a high second-round pick in 2015 (33rd) to the New York Islanders for a defenceman, Griffin Reinhart, who had played eight NHL games to that point. Reinhart only ended up playing 29 total games for the Oilers, while recording one assist in that time. The 16th-overall pick turned out to be Mathew Barzal, a Calder Trophy winner. While the 33rd-overall selection turned out to be Mitchell Stephens, a centerman who is projected to centre the fourth line for the Detroit Red Wings this coming season. Reinhart left for Europe after playing three and a half seasons in the AHL, split between Bakersfield and the Chicago Wolves, the Vegas Golden Knights’ affiliate.
The fans seemed to have turned on Justin Schultz after he regressed by a large margin in 2015-16, his last with the Oilers. Chiarelli traded him for a third-round pick in that year’s draft halfway through the season. Schultz went on to record almost as many points in 10 games with the Pittsburgh Penguins as he did in 45 games in Edmonton that season. He also won the Stanley Cup with Pittsburgh that season and next, posting career numbers in the 2016-17 regular season and playoffs. The third-round selection turned out to be Filip Berglund, a prospect that is still in the Oilers’ organization. His value is yet to be seen.
Probably the infamous trade that everybody in Edmonton knows Peter Chiarelli for is the 1-for-1 swap of Taylor Hall and Adam Larsson. This saw a former first-overall pick who could skate and score traded away for a former fourth-overall pick who was a defensive defenceman. Sure, Larsson is a very good defensive player, but those types of players are easier and cheaper to come by than scoring wingers. Hall ended up winning the Hart Trophy the very next season in New Jersey and led them to the playoffs. Larsson has been a solid addition to Edmonton’s back end for five seasons, but the Oilers have been trying to fill the hole that has been on the wing since Hall left. There has been a rotating door on the first-line left wing position beside McDavid, and who better to keep up with him and put up points than Hall.
Longtime Oiler Jordan Eberle’s trade to the Islanders was the start of an ugly succession that saw Eberle turn into Ryan Spooner under Chiarelli’s watch. This started with an Eberle-for-Ryan Strome old-fashioned hockey trade. This freed up $3.5 million, but the team lost yet another high-profile winger. Strome underperformed compared to his breakout season in 2014-15, and Edmonton didn’t get what they had hoped for. This trade was pulled off after Eberle’s poor performance in the playoffs, recording two assists in 13 games. Since then, the Islanders have made the playoffs in three of four seasons since Eberle joined, and he has put up great numbers, posting 34 points in 49 games in three postseasons.
Strome was traded the next season to the Rangers after starting horribly in a 1-for-1 deal that sent Spooner back. Spooner had also been having a terrible start to the season after seemingly breaking out in 2015-16 and continuing it in 2017-18 once he joined New York. He recorded three points in 25 games for the Oilers before being sent down to the minors and not playing another game for Edmonton. This small succession featured a former first-rounder who put up 76 points in a season to a player who recorded over 40 points once in his short NHL career.
The last trade that Chiarelli pulled off in Edmonton was trading away a hard-working winger in Drake Caggiula in a 2-for-2 trade that brought back Brandon Manning, the player who put McDavid out with a major injury during his rookie season.
Ken Holland
A draft steal in Marino was sent to Pittsburgh by Holland for a sixth-round pick. The next season, Marino played on the team after the Penguins’ defence was depleted. He put up great rookie numbers for a defenceman, recording 26 points and a plus-17 plus/minus in 56 games. The sixth-round pick that Edmonton got in return hasn’t panned out.
Holland made a deal with his former team, Detroit, and traded for Andreas Athanasiou. Athanasiou struggled to produce after coming over and didn’t re-sign with the Oilers. Edmonton sent back two mid-second-round picks that have turned into Brock Faber and Aatu Raty. Before the 2020-21 season, Raty was at the top of everybody’s list to go very high in the 2021 NHL Entry Draft.
With a chance to draft the goalie of the future and a guy who was the top ranked goaltender entering the 2021 Draft, Holland elected to trade the 20th-overall pick to the Minnesota Wild for the 22nd and 90th picks that year. This allowed the Wild to draft Jesper Wallstedt, and Edmonton had to settle for a forward in Xavier Bourgault and another defensive prospect in Luca Munzenberger.
Best Draft Picks/Steals
The more recent the draft, the harder it is to tell if either general manager’s draft picks are steals or busts. Charelli’s picks are easier to tell with half of them, but some, such as Samorukov, we have to look at their development and predict if they will be an impact player.
Peter Chiarelli- 2015-2018
2015 4th round (117)- Caleb Jones was a guy who was in and out of the lineup and up and down from Bakersfield and Edmonton. His play in the defensive zone made him a liability and held him back from taking a step forward with the Oilers and earning full-time minutes.
2015 5th round (124)- Ethan Bear had a solid rookie year in his first full season in the NHL before regressing in 2020-21. Inevitably being traded to improve at forward.
2015 6th round (154)- John Marino seemed to have regressed in his third year at Harvard, but then broke out out of nowhere for Pittsburgh after being traded.
2017 3rd round (78)- Stuart Skinner saw his first big league action last season in one appearance. He looks to impress at training camp and push for some more games for the Oilers this season.
2017 3rd round (84)- Dmitri Samorukov played the entire 2020-21 season in the KHL and was able to put up solid numbers and compete. With all the experience playing against men in Russia, it should help him develop quicker and join the Oilers sooner than later.
2018 2nd round (40)- Ryan McLeod was a part of the most productive line in the AHL last season, which earned him his call-up to the NHL. He immediately slotted in on the third line and showed he can hang with the big boys. McLeod seems to be a lock to make the team in 2021-22 and centre the third line once again, this time with some upgrades at the wing.
Ken Holland- 2019-2021
2019 3rd round (85)- Ilya Konovalov We are already hearing rumblings that Konovalov may be ready to take a step forward and compete for playing time this year on the Oilers. For a goaltender being so young, he has taken massive steps forward in just two seasons since being drafted.
2020 4th round (100)- Carter Savioe and 2020 5th round (126)- Tyler Tullio Since being drafted, both Savioe and Tullio have moved up the depth chart pretty quickly for late-round picks. Look for them to contribute in the AHL next season and raise the expectations even more from there.
It is way too early to tell if any of the players drafted in 2021 are steals or busts.
Draft Busts
Peter Chiarelli- 2015-2018
2016 1st round (4)- Jesse Puljujarvi seemed like a massive draft bust when comparing him to the top-three picks of the 2016 Draft and also Matthew Tkachuk at No. 6. When Puljujarvi left for Europe, it looked like he was either going to stay over there or wait until his contract expired to sign with a different team. Losing a very high pick like that in a year that saw elite talent go after him in the first round would’ve wasted another draft year in an effort to build from within. It doesn’t seem like as much of a draft bust anymore considering how Puljujarvi has played since returning, but he will have to really step up to erase the criticism after being drafted so high.
Ken Holland- 2019-2021
Yet to be seen…
With more time in Edmonton to date, Chiarelli definitely pulled off more big trades, good and bad. The bad overshadows the good here as he seemed to overcompensate for positional needs. Holland took more control in signing big names to an Oilers team that looks to compete every season from here out, signing Nurse, Nugent-Hopkins, Hyman, and Puljujarvi. Chiarelli made three major signings, two of which have put Edmonton in cap trouble by inking Lucic and Koskinen to large AAVs, while he got all he could have hoped for when signing Draisaitl to a cheap deal.
Chiarelli was lucky enough to have some layups with a player like McDavid at first overall, but was also the general manager who put the team in cap trouble still to this day. In my opinion, in the shorter time spent with the Oilers organization, Holland has helped the team more than hurting it thus far and comes out on top. Chiarelli did more harm than good for Edmonton, and that’s a big reason why fans wanted him out. Hopefully, many more years of Holland in Edmonton are to come to try and recapture his former glory and return the Oilers to their dynasty days!
Longtime Edmonton Oilers fan with a background in hockey analytics. Have enjoyed following and writing about the Oilers and the NHL for some time now.