We’re just a few days away from the trade deadline for the 2024-25 NHL season. To say the Edmonton Oilers need to do something would be an understatement. 
The team has been a buyer in each of the past five seasons. Still, they haven’t given Connor McDavid and Leon Draisaitl their first Stanley Cups. Heartbreakingly, Oilers fell just two goals short of doing so in Game 7 of the 2024 Stanley Cup Final.
Even after the additions of Trent Frederic and Max Jones, there are still a few holes for Edmonton to fill ahead of Friday’s 1 PM MT deadline, such as adding another penalty killer, a second-pairing defenceman, potentially a netminder, and even a scoring forward.
With that being said, let’s look at what the Oilers did ahead of the past five trade deadlines with Ken Holland at the helm.

The 2019-20 season: Ken Holland’s deals with Detroit

Starting with the 2019-20 trade deadline, the Oilers made four moves before the global pandemic messed everything up. First up was a small one, moving Joel Persson to the Ducks for Angus Redmond and a 2021 conditional seventh-round pick. The condition that Persson played 20 NHL games in 2020-21 wasn’t met, leaving just Redmond as the Oilers return. Redmond hasn’t played since the 2021-22 season, Petterson plays in Sweden.
Another trade they made was bringing in Tyler Ennis for a 2021 fifth-round pick. Ennis played nine games with the Oilers in 2019-20, scoring two goals and nine points, including a goal and two assists in three games. The following season, Ennis scored three goals and nine points in 30 games. As for the pick, it was used to select netminder Gage Alexander after the Senators traded the pick.
The two most notable trades for this deadline involved Ken Holland’s former team, the Detroit Red Wings. Edmonton moved veteran Kyle Brodziak and the 2020 fourth-round pick to the Wings in exchange for defenceman Mike Green. Unfortunately, Green didn’t really pan out for the Oilers, playing just two games before the global shutdown and appearing in none of their post-season games. The Red Wings used the pick to select netminder Jan Bednar.
Their other move was the bad move, one of the worst moves of the Holland era. In fact, this entire trade tree was something, involving Chris Pronger, Jordan Eberle, and others. After Eberle, the Oilers got Ryan Strome, then Ryan Spooner, and then fan-favourite Sam Gagner in 2019. However, he was traded with the 2020 and 2021 second-round picks to the Red Wings for Andreas Athanasiou and Ryan Kuffner.
Athanasiou played just nine regular season games with the Oilers, scoring one goal and two points, as well as being held pointless in four post-season games. He wasn’t tendered after the season ended and became an unrestricted free agent, signing with the Los Angeles Kings. Speaking of the Kings, the Red Wings traded that pick to move five spots down, while the Kings selected Brock Faber. It’s not the last time an Oiler second-rounder was used to select a future star defenceman.
The Red Wings also traded the Oilers’ 2021 second-round pick to the Islanders, receiving Nick Leddy. That pick was used to select Aatu Raty, who was traded to the Vancouver Canucks in the Bo Horvat deal along with the Islanders’ 2022 first-round selection. That 2022 first-round pick was then flipped to the Red Wings for Filip Hronek and the Wings used it to select future star defenceman Axel Sandin Pellikka. Sure.
Anyway, thanks to the COVID pandemic, the regular season was cut short and there was a playoff qualifier, where the Oilers fell in four games (in a best of five) to the Chicago Blackhawks. Yikes.

The 2021 season: A quiet deadline for a shortened campaign

The global pandemic also impacted the 2020-21 season, cutting it down to 56 games and creating an eight-team Canadian division. The Oilers only made one move ahead of that deadline, trading their 2022 fourth-round pick to the New Jersey Devils for Dmitry Kulikov, a rental.
Kulikov was brought in as a bottom pair, penalty killing defenceman and he was solid. In 10 games after the trade, he picked up two assists and was a plus-one. He played three post-season games with the Oilers, before signing with the Minnesota Wild before the 2021-22 season.
That pick was used to select Charlie Leddy, a 21-year-old right-shot defenceman who is a junior at Quinnipiac University after two seasons at Boston College.
In the 2021 post-season, the Oilers were goalie’d by Connor Hellebuyck, as they were swept in four games that they dominated.

The 2021-22 season: Another quiet trade deadline

For the third consecutive trade deadline, Ken Holland sat on his hands and decided not to go all in. He made two trades at the deadline, with one of them still impacting the Oilers to this day, as well as the team they traded with.
But first, let’s look at the smaller move, trading the 2023 fourth-round pick to the Philadelphia Flyers for Derick Brassard. The right-shot centre was a hero of the Ottawa Senators postseason run in 2017, but he was well past his prime when joining the Oilers in 2022, scoring just two goals and three points in 15 games and playing just one post-season game. With the pick, the Flyers drafted Alex Ciernik, a 20-year-old German who currently plays in Sweden’s second tier.
The other trade was far more meaningful, as the Oilers traded their 2022 second-round pick, defenceman William Lagesson, and a 2024 seventh-round pick to the Montréal Canadiens for Brett Kulak. 
Kulak is a steady third-pair defenceman who is still with the Oilers, scoring two goals and eight points in 18 games after the trade. He’s still with the team and has a career-best seven goals and 21 points in 61 games this season, a good trade no matter what way you slice it.
It was a good trade for the Canadiens as well. That 2022 second-round pick was used to select defenceman Lane Hutson, who has four goals and 48 points in 61 games this season and is a front-runner to win the Calder Memorial Trophy. Laggeson is a defenceman who hasn’t had the same success, as he’s spent the majority of this season with the Detroit Red Wings American Hockey League team.
Selected with the seventh-round pick was left-shot defenceman Rasmus Bergqvist. He represented Team Sweden in the most recent World Junior Championship, scoring a goal and three points in seven games.
The 2022 post-season was the first time the Oilers did any damage in the playoffs, defeating the Los Angeles Kings in seven games in the first round, before bouncing the Calgary Flames in the second round. Unfortunately, the Oilers were swept by the Colorado Avalanche in the Western Conference Final.

The 2022-23 season: The splash fans had been waiting for

The 2023 trade deadline was my first with Oilersnation and it’d be hard to say it wasn’t the best of the five deadlines we’ll look at in this article. One move was needed to make the other move just a few hours later several days before trade deadline day while the Oilers made a move on trade deadline day. Let’s start with the latter.
On March 2, the Oilers traded a 2023 third-round pick and right-shot defenceman Michael Kesselring to the Arizona Coyotes in exchange for Nick Bjugstad and Cam Dineen. Bjugstad had a solid showing with the Oilers, scoring four goals and six points in 19 regular season games, as well as three goals in 12 post-season games. However, he re-signed with the Coyotes in the off-season. 
Dineen, a left-shot defenceman, has five goals and 29 points in 45 games with the American Hockey League’s Bakersfield Condors. He was recently called up to the Oilers but didn’t play a game.
What the Oilers gave up was… a lot. The draft pick was used to select Belarussian right winger Vadim Moroz – no relation to Oilers’ second-round 2012 draft pick Mitch Moroz. This season in the Kontinental Hockey League, V. Moroz has 21 goals and 37 points in 58 games as a 21-year-old.
Losing Kesselring hurts the Oilers far more though. This season, the right-shot defenceman has a career-high six goals and 23 points in 61 games. He’s a big-bodied defender as well, standing at 6’5”, 215 lbs with a hard slap shot. That would’ve been nice to have on the second pairing.
The first move the Oilers made before the deadline was trading Jesse Puljujärvi to the Carolina Hurricanes for Patrik Puistola. Puljujärvi, the fourth-overall pick in the 2016 draft, had a cap hit of $3 million and trading for an un-signed prospect was solely to take money off the books for the larger move later that day.
Because about six hours later, the Oilers traded Tyson Barrie, 2022 first-round pick Reid Schaefer, a 2023 first-round draft pick, and a 2024 fourth-round draft pick to the Nashville Predators for Mattias Ekholm and a 2024 sixth-round draft pick.
Of all the moves the Oilers made at the past five trade deadlines, this was the only one where they really went all-in. Ekholm scored four goals and 14 points in 21 games to end the season and had a goal and seven points in 12 post-season games. He scored a career-high 11 goals and 45 points in 79 games last season, adding five goals and 10 points in 25 post-season games.
In 2024-25, the Swedish left-shot defenceman has eight goals and 27 points in 60 games, playing key minutes on the top pairing along with Evan Bouchard.
They didn’t give up a whole lot either. Tyson Barrie played 24 games with the Predators, scoring three goals and 12 points in 24 games. The right-shot defenceman only played 41 games in 2023-24, scoring a goal and 15 points before signing with the Calgary Flames in 2024-25, where he’s played 13 games with a goal and three points. Barrie currently plays for the American Hockey League team.
Schaefer joined the Predators’ AHL team in 2023-24, scoring seven goals and 21 points in 63 games, along with a goal and three assists in 14 post-season games. So far this season, he has eight goals and 14 points in 19 AHL games.
As for the two picks, the first-round pick in 2023 was used to select left-shot defenceman Tanner Molendyk, who has six goals and 40 points in 44 Western Hockey League games this season. The 2024 fourth-round pick was later traded to Tampa Bay, who used it to select Hagen Burrows, a right-wing who is a freshman at the University of Denver. Edmonton used their 2024 sixth-round selection to pick defenceman Albin Sundin.
The 2023 post-season didn’t end well for the Oilers, as they fell in six games to the Vegas Golden Knights in the second round. It was the second consecutive season that the Oilers fell to the team that went on to win the Stanley Cup.

The 2023-24 season: Multiple additions ahead of a deep run

Last up, we come to last season’s trade deadline. On March 7, the Oilers made a small move, trading their 2027 fourth-round pick to the Arizona Coyotes for Troy Stecher (who they re-signed) and a 2024 seventh-round pick. 
Stecher played seven games with the Oilers in 2023-24, picking up two assists. So far in 47 games, he has three goals and six points in 46 games, a perfect seventh defenceman. The Oilers used the seventh to select left-shot defenceman Bauer Berry.
The other move had more of an impact. A day before the trade deadline, the Oilers traded their 2024 first-round pick and a 2025 fifth-round pick to the Anaheim Ducks for Adam Henrique, Sam Carrick, and a 2024 seventh-round pick. The Oilers also traded their 2025 fifth-round pick to the Tampa Bay Lightning for unsigned prospect Ty Taylor and an additional 50% retention on Adam Henrique’s deal.
Say what you want about Henrique (he’s a good third line centre), but he was important for the Oilers in their Stanley Cup run in 2024. He scored six goals and nine points in 22 games after the trade, including four goals and seven points in 17 post-season games. So far in 2024-25, Henrique has eight goals and 17 points in 60 games while being an important penalty killer for the team.
Sam Carrick played 16 games after the trade, scoring two goals and five points in 16 games, as well as 10 post-season games with an assist and speared a Panther at the end of a game. He signed with the New York Rangers in the off-season, where he has five goals and 17 points in 61 games.
As for the pick, the Ducks used the pick to trade up in the draft, selecting Stian Solberg with the 23rd overall pick. The left-shot defenceman became the second Norwegian player picked in the first round, eight picks after the Detroit Red Wings selected Michael Brandsegg-Nygård.
The Oilers also got a pick in the draft and it’s starting to look like a steal. With the Ducks’ seventh-round pick, they selected William Nicholl 196th overall. So far in 56 games with the Ontario Hockey League’s London Knights, he has 17 goals and 49 points in 56 games, not too shabby for a player selected so late.
Ryley Delaney is a Nation Network writer for Oilersnation, FlamesNation, and Blue Jays Nation. They can be followed on Twitter @Ryley__Delaney.