Comparing Ken Holland and Peter Chiarelli’s drafting and why the Oilers shouldn’t be afraid to move picks

Brennan Delaney
1 month ago
The Edmonton Oilers will be facing Ken Holland’s former team on Tuesday as the Detroit Red Wings are making their way through town.
Back in January of 2019, the Wings came to Edmonton and edged out a 3-2 win over the Oilers. That loss marked the end of Peter Chiarelli’s tenure as general manager of the Oilers, likely because Holland gave them the thumbs up that he’d be interested in the job in a few months.
Since then, the Oilers have made the playoffs in each of Holland’s four seasons as general manager, though the much-maligned Chiarelli has actually helped his predecessor’s cause. But before getting into how Chiarelli’s drafting continues to impact the Oilers today, let’s establish that his time in Edmonton was very rough for a variety of reasons.
In terms of contracts, Milan Lucic signing a six-year, $7 million per year deal sticks out like a sore thumb. Giving Kris Russell a four-year, $4 million annual deal was less than ideal, while Mikko Koskinen’s three-year, $4.5 million per year cap signing was one last “screw you” to the Oilers a day before Chiarelli’s firing.
Trading-wise, you need not look any further than trading long-time Oiler and fan favourite Jordan Eberle for Ryan Strome. That move wasn’t awful in and of itself, but moving Strome for Ryan Spooner was a disastrous move. Or when he moved Taylor Hall for Adam Larsson, an okay move in reality, but painful once Hall won. Also trading for Brandon Manning when he injured Connor McDavid has got to be one of the dumbest moves any general manager has made.
The worst of his trades as an Oiler though, was moving the 16th-overall pick and the 33rd-overall pick in the incredibly deep 2015 draft. Not only because those two picks were moved for Griffin Reinhart, who was already seen as a bust at that point, but because Chiarelli was actually good at drafting. We just didn’t realize it until several years after he was fired.
In this article, we’ll look at Chiarelli’s good drafting and how it still impacts the Oilers today, as well as how new general manager Ken Holland has done with it.

Jan 20, 2024; Calgary, Alberta, CAN; Edmonton Oilers goaltender Stuart Skinner (74) guards his net against the Calgary Flames during the second period at Scotiabank Saddledome.

A look at Peter Chiarelli’s solid run of drafting with the Oilers:

With his first-ever pick as an Oilers general manager, Chiarelli drafted the one and only Connor McDavid in 2015 with the first overall pick.T hey also had the 16th-overall pick, where Mathew Barzal, Kyle Connor, Thomas Chabot, Joel Eriksson Ek, Brock Boeser, and Travis Konecny were available, as well as the 33rd-overall pick, where Sebastian Aho was picked two picks later and Brandon Carlo four picks later, but whatever.
That being said, the 2015 draft was still successful, as he picked Caleb Jones with the fourth-round pick, Ethan Bear with the fifth-round pick, and John Marino with the sixth-round pick. All three of these late-round defenceman have formed some type of role in the National Hockey League.
The Oilers also had a high pick in the 2016 draft, picking Jesse Puljujärvi with the fourth overall selection. In hindsight, this wasn’t a great selection due to how Puljujärvi’s career has unfolded, but the Oilers were seen as lucky to land him. This was Chiarelli’s only miss as the Oilers general manager.
Along with Puljujärvi, the Oilers selected Tyler Benson with their second-rounder and Markus Niemeläinen with their third-round pick. Both have played around 40 games in the NHL, but Vincent Desharnais was his best selection in 2016, as he has played 82 games as an Oiler and stapling himself as Edmonton’s third pairing right-shot defenceman.
In 2017, the Oilers had a late-first-round pick for the first time in a long time, selecting Kailer Yamamoto with the 22nd overall pick. In his career, he has scored 57 goals and 130 points in 288 games, helping the Oilers make the playoffs in 2019-20. Stuart Skinner was the other notable pick so far in that draft, as he has a .912 save percentage and a 2.64 goals-against average in 100 games so far. Not bad for a 78th-overall pick.
For the second draft in a row, the Oilers’ seventh-round pick has played in the NHL, as Philip Kemp played a game earlier this season, logging just a handful of minutes as the seventh defenceman. The 25-year-old right-shot defenceman had six goals and 21 points in 71 games with the Bakersfield Condors in 2022-23. This season, he has just six points in 32 games but could be a depth option for the future.
The 2018 draft was Chiarelli’s magnum opus. With the 10th overall pick, he selected Evan Bouchard, Edmonton’s first real puck-moving defenceman, an offensive defenceman that they drafted and developed forever. With their second-round pick, the Oilers selected Ryan McLeod, who has turned into a young, defensively responsible third-line centre. Michael Kesselring was involved in the Nick Bjugstad trade at the 2023 deadline but has played 42 games with four goals and 10 points with the Arizona Coyotes.
In terms of the future, Olivier Rodrigue has become one of Edmonton’s top prospects, posting a .922 save percentage and a 2.56 goals-against average in 19 games played in the American Hockey League this season. The 23-year-old could be ready within the next two seasons and could form a great tandem with Skinner.
Chiarelli was fired on January 23, 2019, and for good reason. Despite the fantastic drafting which has really helped the Oilers in Holland’s tenure, the trades and the signings were detrimental to Edmonton’s success when he was here.

Apr 8, 2023; San Jose, California, USA; Edmonton Oilers defenseman Philip Broberg (86) chases after the puck during the second period against the San Jose Sharks at SAP Center at San Jose. Mandatory Credit: Stan Szeto-USA TODAY Sports

Ken Holland’s drafting with the Oilers has left a lot to be desired:

If you merge Ken Holland and Peter Chiarelli, you’d have a solid general manager. Of course, Holland has a fair share of “why would you sign this guy” and “why would you trade for this guy” deals. The most notable has to be Darnell Nurse’s eight-year, $74 million. Nurse is a great defender, but not worth the contract he’s making. Of course, you also have Hyman signing a seven-year, $38.5 million deal, or the Mattias Ekholm and Warren Foegele trades, definite wins already.
Where Holland has struggled, is with the draft. Between 2019 and 2023, the Oilers have only seen three players that they’ve drafted suit up for the big league club to this point. With the Oilers in win-now mode, Holland has traded quite a few picks to improve the team, but he also hasn’t been able to find the mid-to-late-round gems like he did while in Detroit. 
In 2019, he had the eighth-overall pick and selected Phillip Broberg, who has played 79 games in the NHL with two goals and 11 points. Defenders take forever to develop, but with Trevor Zegras, Matthew Boldy, Cole Caufield, and Thomas Harley still on the board, this may not have been a great pick. In the second round, they selected Raphael Lavoie, who could be a useful middle-six player in the future for the Oilers. Matěj Blümel is the only other player to have made his NHL debut, playing six games for the Dallas Stars in 2022-23.
The 2020 draft was probably Holland’s best draft as an Oiler general manager, selecting Dylan Hollway with the 14th overall pick. He has scored five goals and 12 points in 72 games, and has looked good when healthy this season. On top of that, there weren’t a lot of great players picked after him other than maybe Dawson Mercer, who has 58 goals and 122 points. The team’s later-round picks, such as Ty Tullio and Carter Savoie, show promise but still have room to grow before getting a shot at the NHL level. 
Where issues arise is the 2021 draft. The Oilers held on to the 20th-overall pick but traded down to the 22nd-overall pick to also pick up a later-round pick. The Minnesota Wild selected Jesper Wallstedt, one of the best goaltending prospects in the league, while the Oilers would’ve also had a chance to select Fabian Lysell, who was picked 21st overall. 
Instead, the Oilers picked Xavier Bourgault, who has just six goals and 16 points in 40 AHL games this season. For context, Bourgault had 13 goals and 34 points in 62 games in 2022-23, so there’s already been some regression. It also doesn’t help that Wyatt Johnston was picked one selection after, and he already has 39 goals and 74 points in 134 games with the Dallas Stars.
The Oilers selected Reid Schaefer with the 32nd overall pick in 2022 (they moved down to get rid of Zack Kassian’s contract). They packaged him, alongside Tyson Barrie and their first-rounder in 2023, for Mattias Ekholm, which brings me to my next point. 
It’s believed that this will be Holland’s last season as a general manager, as his contract is coming to an end following 2023-24. He stated at the beginning of the season that this is “a Stanley Cup or bust season” for the Oilers, so why even bother picking players?
This season, the Oilers have their first, second, fifth, and sixth-round picks, along with an additional sixth-rounder. None of those players, except for maybe the first-rounder, will be of use to the Oilers before Leon Draisaitl and Connor McDavid’s contracts run out. 
The Oilers need to go big or go home, and what better move is there than trading the first-round pick for an impact player like they did in 2024? Imagine landing Jake Guentzel, or a defenceman similar to Ekholm, but right-handed. Screw drafting at this point, go for broke and win the damn Cup.

If you enjoy my content, you can follow me on Twitter @Brennan_L_D.
Updated: Links and spelling (2/13/2024)

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