Ken Holland's tenure as the General Manager of the Edmonton Oilers, which concluded in 2024, was marked by a mix of shrewd moves and questionable decisions that significantly impacted the team's trajectory. While he successfully guided the Oilers to the playoffs in each of his five seasons, his legacy is defined by both his successes and failures in building a Stanley Cup contender.

The Best Moves

1. Acquisition of Mattias Ekholm: Arguably Holland's most impactful move was trading for defenseman Mattias Ekholm from the Nashville Predators in 2023. The cost was Tyson Barrie, prospect Reid Schaefer, and a 2023 first-round pick. Ekholm's arrival transformed the Oilers' blue line, providing stability and a strong defensive presence. His pairing with Evan Bouchard became one of the league's best. Trading Barrie also allowed Bouchard to take over the top power play quarterback role, where he excelled, reaching a career-high of 81 points in the 2024-2025 season. The acquisition of Ekholm is considered the franchise's best trade since Chris Pronger.
2. Signing of Zach Hyman: Holland's signing of Zach Hyman as a free agent was a resounding success. Hyman brought a strong work ethic and scoring touch to the Oilers' top-six forward group. He consistently drove to the net and contributed timely goals, becoming a fan favorite. Hyman's performance exceeded expectations, making him one of Holland's best free-agent signings.
3. Hiring Kris Knoblauch: After a dismal 3-9-1 start to the 2023-24 season, Holland made the bold decision to fire head coach Jay Woodcroft and hire Kris Knoblauch. This move proved to be a catalyst for the Oilers, as Knoblauch led the team to a 46-18-0-5 record over the next 69 games. Knoblauch instilled a new system and approach, helping the Oilers achieve a 16-game winning streak shortly after his arrival, narrowly missing the NHL record.

The Worst Moves

1. Signing of Jack Campbell: Holland's biggest misstep was signing goaltender Jack Campbell to a five-year, $25 million contract. Campbell struggled mightily in Edmonton, failing to provide the stability the Oilers desperately needed in net. He was eventually demoted to the American Hockey League (AHL) after just a handful of appearances in his second season. Campbell's poor performance and high salary made this signing a major setback for the Oilers.
2. Extension of Zack Kassian: In 2020, Holland signed Zack Kassian to a four-year, $12.8 million extension following a career year. However, Kassian's production declined sharply after signing the deal, and he struggled to maintain the physical edge that had made him effective. The contract quickly became an overpayment, and Kassian was eventually traded.
3. Andreas Athanasiou Trade: Holland traded two second-round picks (which became Aatu Raty and Brock Faber) and Sam Gagner to the Detroit Red Wings for Andreas Athanasiou. Athanasiou failed to make a significant impact with the Oilers, registering only one goal and one assist in nine games. Faber, on the other hand, became a Calder Trophy finalist with the Minnesota Wild. This trade is viewed as a significant loss for the Oilers, especially considering Faber's success.

Overall, Ken Holland's tenure as GM of the Oilers was a mixed bag. While he made some excellent moves that significantly improved the team, such as acquiring Mattias Ekholm and signing Zach Hyman, he also made some poor decisions that hampered the team's progress, most notably the Jack Campbell signing. Despite these errors, Holland brought the Oilers to the playoffs each year and brought them closer to being a true contender.