Best And Worst Trades of Ken Holland’s Oilers Tenure so Far

Best Trades:

Oilers Acquire: Brett Kulak (50% Salary Retained)

Canadiens Acquire: William Lagesson, 2022 second-round pick, 2024 seventh-round pick

The Oilers decided not to go all-in with a big splash at the 2021 trade deadline, partially due to the tight salary cap situation. Instead, they acquired Brett Kulak to bolster the left side of the defense group for the upcoming playoff run.

This was seen as a minor addition at the time but with Nurse sustaining a torn hip flexor, Kulak needed to take on a little more responsibility than what was originally expected of him, and he delivered. Kulak skated well throughout the playoffs and his ability to defend off the rush was sorely needed with a banged-up Darnell Nurse and the slower Duncan Keith joining him on the left side. Kulak was one of the most consistently steady defensemen on the team this spring, and a big reason they were able to make it to the conference final.

All Ken Holland had to give up to acquire him was a fringe NHL defenseman in Willian Lagesson, and a couple of draft picks. While the deal was only seen by many as a rental at the time, Kulak has been such a nice fit on this team that he should be a priority to resign this summer.

He proved his ability to play in the top four, and if Keith retires or needs to slide down to the third pair next season, Kulak could be an affordable top-four option.

Oilers Acquire: Tyler Ennis

Senators Acquire: 2021 fifth-round pick

A bargain-bin acquisition made at the 2020 trade deadline, Tyler Ennis provided Edmonton with a pretty good bang for their buck. The Oilers only had to give up a fifth-round pick in the trade, and Ennis came in at a minuscule cap hit of 800k.

He went on to produce 13 points in 39 games with mostly positive underlying numbers. Not bad for a player that cost next to nothing to acquire and had an affordable contract.

Oilers Acquire: 2020 fourth-round pick (Carter Savoie), 2020 fifth-round pick (Tyler Tullio)

Sharks Acquire: 2020 third-round pick (Danil Gushchin)

This trade may be more a testament to the Oilers’ drafting than it is to Ken Holland’s trading ability, but no matter which way you slice it, this has a chance to be a sweet deal in a couple of years. The Oilers traded their 2020 third-round pick to San Jose in order to acquire two picks later in the draft that they used to select Carter Savoie and Tyler Tullio. Each of these prospects are developing extremely well and have a ton of upside. San Jose chose Danil Gushchin with Edmonton’s pick, and while he does have some potential, Tullio out-produced him in the OHL this past season and Savoie has looked fantastic with the University of Denver. It may be too early to be taking victory laps on this deal but as of now I would say the Oilers got two decent prospects for the price on one here, and you could argue they got the two best players in the deal.

Worst Trades:

Oilers Acquire: Warren Foegele

Hurricanes Acquire: Ethan Bear

This trade was a controversial one at the time it was made, but I think the most shocking result of this trade is that both teams appear to have lost the deal. The Hurricanes have such a deep defense core that Bear wasn’t able to find a consistent role on the team, and while Foegele wasn’t horrible by any means, he failed to provide as much depth scoring as the Oilers had hoped.

Foegele also struggled in the playoffs, becoming a healthy scratch at one point, which is a tough pill to swallow when the Oilers had to give up a young player with some decent upside in order to get him.

While it may have been a valid concern to have a right-side defense group of Ceci, Bouchard, and Bear due to the reliance on young players, overpaying for Barrie to play the third pair for most of the year hasn’t turned out to be an ideal fit either. Perhaps keeping the cheaper and younger Ethan Bear would have given the Oilers more options and more wiggle room to make upgrades to the roster later.

We will never know how it would have worked out if the Oilers kept Bear, but this deal hasn’t really worked out the way either team had hoped.

Oilers Acquire: Duncan Keith, Tim Soderlund

Blackhawks Acquire: Caleb Jones, 2022 third-round pick

The Duncan Keith deal was one of the most controversial trades in the NHL during the summer of 2021. Keith’s numbers had seen a steady decline for several years, culminating in a disastrous 2019-20 season for him and most of the Blackhawks roster.

Many analytics followers such as myself saw the trade as a major risk. Sure he has a ton of experience, but the numbers suggested he began to have a difficult time keeping up once his footspeed started to fade with age. Luckily, in a reduced role with the Oilers, he was able to have somewhat of a bounce-back season as a serviceable if not a slightly inconsistent second-pair defenseman.

This trade might not have been so bad in a vacuum, but in a world where salary matters, the obvious problem with this deal is that the Oilers were unable to get the Blackhawks to retain any salary. Keith makes a hefty $5.5m AAV that he can never hope to live up to at this age and it has put the Oilers in a tight cap situation.

Perhaps the most frustrating part of this whole ordeal is that Duncan Keith requested a trade to a team in the northwest, giving Stan Bowman limited options for a trade. The fact that Holland wasn’t able to use any negotiating power to at least get some salary retained is a big loss, especially considering they were able to acquire the younger, cheaper, and more consistent Brett Kulak for a similar bundle of assets later on.

Oilers Acquire: Andreas Athanasiou, Ryan Kuffner

Red Wings Acquire: Sam Gagner, 2020 & 2021 second-round picks

At the 2020 trade deadline, fan-favorite Sam Gagner was traded along with two second-round picks to the Red Wings in exchange for Andreas Athanasiou. The deal ended up being a colossal disappointment, as Athanasiou only managed two points in thirteen games with the Oilers, a lower rate of production than Gagner got in a bottom-six role that season.

Those who were hopeful for a better season from Athanasiou the next time around had those hopes crushed when Holland didn’t even qualify AA in the offseason, allowing him to leave in free agency. Just a few months later, Devon Toews was dealt by the New York Islanders to the Colorado Avalanche as a cap dump for just a pair of second-round picks.

It sure would have been nice to have acquired a star player for that price, but instead, Holland fumbled those assets away for almost nothing, making this arguably his worst deal as Oilers general manager.