Ken Holland’s Trades & Signings in 2021-22 Key to Oilers’ Success

Edmonton Oilers general manager Ken Holland was very busy this past season, and though he might not get the credit he deserves, he made key changes to the team and organization that contributed to their success. We’ll start by looking at the offseason that set up this great run the Oilers had in 2021-22, then jump to the mid-season moves that made a huge difference, before finishing up with a few of his bad decisions, because nobody’s perfect.

Solid 2021 Offseason Moves Made by Holland


Holland and the Oilers made some big trades last offseason that resulted in a shift in their lineup. Unfortunately, Oscar Klefbom wasn’t able to recover for the 2021-22 season, so something had to be done to replace their second pairing left defence spot. Acquiring Duncan Keith was ultimately the big trade that Holland pulled off. It was criticized and still doesn’t look the greatest in terms of the cap hit Keith has, but he was key in helping defence partner Evan Bouchard grow in his first full season in the NHL.

Keith brought playoff experience that came in handy as the Oilers made the Western Conference Final despite his struggles at times and the number of goals against his pairing. The trade in acquiring Keith from the Chicago Blackhawks saw Caleb Jones and a 2022 third-round pick head the other way as one of the only moves Holland believed he could make to adequately add a top-four left defenceman.

Duncan Keith Edmonton Oilers
Duncan Keith, Edmonton Oilers (Jess Starr/The Hockey Writers)

The Warren Foegele/Ethan Bear trade looked to be just about equal throughout the season for the Oilers and the Carolina Hurricanes until Bear was scratched for the entire playoffs and only played 58 games during the regular season. Foegele played all 82 and 13 of the 16 playoff games where he wasn’t very effective offensively. The Oilers still got 12 goals out of their player in the deal in a bottom-six role, and have more hope for the future with Foegele over the Hurricanes with Bear, considering they may be looking to trade Bear this offseason.

The other trade that was pulled off by Holland occurred at the 2021 Draft where the Minnesota Wild wanted to move up a few spots in the first round to acquire their starting goaltender of the future in Jesper Wallstedt. The Oilers moved down two spots and drafted Xavier Bourgault instead, who is having an incredible junior season while using the third-round pick they received to take Luca Munzenberger. Considering the Oilers have Stuart Skinner, Olivier Rodrigue, and now Ryan Fanti in their goaltending pipeline, this move turned out good for the future as the Oilers also don’t need a goaltending prospect, they need one right now.


The Oilers made four good signings this past offseason and one intelligent buyout, while also making a couple of bad signings which we’ll get into further down. Of the four good signings, there is no question about three of them which saw them bring back Kailer Yamamoto on a one-year bridge deal, Ryan Nugent-Hopkins to an eight-year extension to keep him as a career Oiler, and Zach Hyman from free agency.

Zach Hyman Edmonton Oilers
Zach Hyman, Edmonton Oilers (Jess Starr/The Hockey Writers)

The iffy signing that had to be done was the contract given to Darnell Nurse. He saw the other young top defencemen around the league getting paid a ton of money, so the Oilers had to give him that if they wanted to keep their number one defenceman. It’s not exactly the easiest for the Oilers to attract free agents with the heavy tax and location of the team, so locking down players who are willing to sign is a must and Holland did just that. The contract may not look the best since he doesn’t play on the power play, but he logs a ton of minutes and will improve from his playoff performance, considering he should be all healed up and not dealing with a torn hip flexor the next time around.

The contract of Yamamoto allowed him to prove to the Oilers that he is worth keeping around long term, and it seems as though the team and both Connor McDavid and Leon Draisaitl prefer him over Jesse Puljujarvi. As for Nugent-Hopkins, he took a discount to stay in Edmonton and is as loyal as players come. He can play in all situations and gives the Oilers the ability to run their three big centermen down the middle or load up the top-six. Finally, Hyman was possibly the best offseason signing of 2021 considering he finished the regular season with 27 goals and 54 points while scoring 11 goals and 16 points in 16 playoff games.

The Oilers also bought out the contract of James Neal that had two years remaining on it to save themselves paying $5.75 million for next season and last, having to only allot $1.917 million for four years instead.

Mid-Season Moves Huge for Oilers

As much of an impact as the players traded for and signed made a difference last season, Holland made the move of the year in signing Evander Kane for only $2.109 million against the cap, only for him to become one of the most impactful players in the NHL (regular season and playoffs) for the remainder of the season.

Connor McDavid Evander Kane Edmonton Oilers
Connor McDavid and Evander Kane of the Edmonton Oilers celebrate a goal (Photo by Andy Devlin/NHLI via Getty Images)

Kane scored 22 goals and 39 points, was a plus-25 in 43 games during the regular season and joined the Oilers at the perfect time, as they were just coming out of their horrible mid-season slide. He turned his game to a whole new level in the playoffs after he was reunited with McDavid and Draisaitl to form a dominant first line. He ended up scoring 13 goals and 17 points in 15 games and recorded two postseason hat tricks. The Oilers would not have been able to go as far as they did without his scoring and physical contributions.

An underrated trade that many thought was an overpayment was acquiring the services of Brett Kulak at the trade deadline for a 2022 second-round pick, 2024 seventh-round pick, and William Lagesson. Kulak shored up the third pairing and made any partner he played with better. He was also a massive help to Tyson Barrie and even added some offence to the mix with two goals and eight points in 18 games.

The Oilers also went out and made a trade with the Philadelphia Flyers for Derick Brassard, who didn’t have a big impact at all after scoring in his first game with the team. He finished the season with two goals and an assist while playing just one playoff game. It only cost them a fourth-round pick in 2023 so it’s not a massive miss.

Along with the mid-season acquisitions, the Oilers also signed three players that should all fit in some way or another in the future, as Holland brought back Dmitri Samorukov and Markus Niemelainen on defence while inking Carter Savoie to an entry-level deal once he finished his season at the University of Denver.

Jay Woodcroft Edmonton Oilers
Jay Woodcroft, Edmonton Oilers head coach (Photo by Andy Devlin/NHLI via Getty Images)

Maybe the most important move during the season, along with signing Kane, was giving the coaching reins to Jay Woodcroft. The former Bakersfield Condors bench boss helped the Oilers turn their season around and go 26-9-3 while massively improving the team defence so that all three goaltenders could record shutouts in the second half of the season after failing to record even one as a team in the first 43 games.

The Bad Decisions in the Past Year

With the good also comes the bad. Fortunately for the Oilers and Holland, the former massively outweighed the latter over the course of the past year. The few moves that either didn’t work out or don’t look good now include, re-signing Mike Smith, Barrie, and Slater Koekkoek, while not moving Mikko Koskinen/Smith at any point during the season.

There were opportunities throughout the season, and even before, to change the goaltending situation by moving one or both of Smith and Koskinen, but Holland decided to run the entire season with the tandem he committed to for two seasons in a row now. Woodcroft helped change the tune of the defence and goaltending to take some pressure off of Holland, but ultimately the offence carried the Oilers to the Western Conference Final, not the goaltending.

Related: Oilers’ Top 3 Goalie Trade Targets if They Can’t Upgrade in Free Agency

As for re-signing Barrie and Koekkoek, keeping a power-play specialist around is important, especially with the dominance that the Oilers’ power play has. It may not have been the worst move at the time of the signing, considering Bouchard had only played 21 NHL games, but it quickly turned into a bad contract when Bouchard passed Barrie on the depth chart and even took away significant time on the power play from him as well. The Oilers shouldn’t be disappointed in the production Barrie had this past season as he improved his all-around game. Though, he is a luxury they can’t afford to pay on their third pairing.

Koekkoek only played 19 games with the Oilers and was sent down to the American Hockey League (AHL). Essentially, they are just wasting a bit of money to keep him down there for one more season, considering he has been passed by a number of young defencemen in the organization.

Overall, Holland did a great job in signing and trading for players considering the cap situation he was in. Every general manager is going to make bad moves, and although the failure to acquire a legitimate starting goaltender may have cost the Oilers Round 3, they still exceeded expectations and things can only go up from here.

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