Ken Holland has made many trades as Edmonton Oilers general manager over the past four years. Here are his best deals.

Ken Holland's is going into the final year of his five year contract with the Edmonton Oilers. In four years with the organization he has completed 21 trades. Surprisingly, there are quite a few that are average or didn't work out. While taking chances is part of the job let's take a look at five times he took a chance that paid off.

Milan Lucic for James Neal

Holland put his stamp on the Oilers roster with this, his first trade as the general manager. On July 19th, 2019 he sent Milan Lucic and a conditional 3rd round 2021 draft pick to the Calgary Flames for forward James Neal. At the time of the transaction the Lucic contract was not a buy out friendly agreement. 

Making the swap allowed the Oilers some cap flexibility down the road. It gave them another potential offensive weapon to give the team scoring depth. Neal went on to tally up 31 points including 19 goals in 55 games in the 2019-20 regular season. Ultimately he was bought out by the Oilers two years after being acquired. 

Zach Kassian & Picks for 2022 1st Round Draft Pick 

Zach Kassian was being paid $3.2 million to be a 4th line player for the Oilers. So at the 2022 NHL Entry Draft, Holland sent a package of Kassian, the 29th overall 2022 draft pick, a 2024 3rd round pick and a 2025 2nd round pick to the Arizona Coyotes for the 32nd overall pick in the 2022 draft. Releaving the team of Kassian's contract would allow them the flexibility to re-sign a few key players such as Evander Kane, Brett Kulak and restricted free agents Kailer Yamamoto and Jesse Puljujarvi. The Oilers would also add Jack Campbell, Calvin Pickard, Greg McKegg, Mattias Janmark, and Ryan Murray through free agency, giving the team depth for the 2022-23 season.

Dmitri Samorukov for Klim Kostin 

Klim Kostin was a great depth player for the Oilers during the 2022-23 regular season. He contributed through secondary scoring as well as a physical prescence. Playing only 57 games for the copper and blue he tallied 21 points and delievered 157 hits. With a $750,000 contract, the Oilers received a lot of bang for their buck with Kostin. Sending defensive prospect Dmitri Samorukov to the St. Louis Blues for Kostin was necessary, as both players needed a change of scenery. 

William Lagesson & Picks for Brett Kulak

On March 21st 2022, the Oilers packaged defence prospect William Lagesson, a conditional 2022 2nd round draft pick, and a 2024 7th round draft pick to the Montreal Canadiens for the Stony Plain born defenceman Brett Kulak. The Canadiens retained 50% of his $1.85 million dollar contract. The hometown player would re-sign with the Oilers the following offseason to the tune of a four year deal at $2.75 million.

Kulak was paired primarily with Tyson Barrie, giving the team much needed depth at defence to make a deep run in the playoffs. He was one of the best Oilers players throughout the 2023 Stanley Cup Playoffs. Despite the dissappointingly early playoff exit, Kulak's play has never dissappointed the Oilers.

Tyson Barrie & Other Assets for Mattias Ekholm

Going into the 2023 Stanley Cup Playoffs the Oilers needed to make an upgrade at defence. That upgrade came in the form of a Trade Deadline deal on February 28th, 2023. The Oilers sent out Tyson Barrie, Reid Schaefer, 2023 1st round pick and 2024 4th round pick for Mattias Ekholm and a 6th round draft pick in 2024. 

The two-way Swedish blue liner would be paired with Evan Bouchard for most of his time with the Oilers. In the playoffs this pairing was the Oilers best. The combination of Ekholm's two way dominance with Bouchard's offensive instincts and slick puck skills made this pairing tough to play against.

By my eye, Holland has done well as Oilers GM. These five trades highlight his value to the organization. He is also able to execute the deals that push the team over the top to be true Stanley Cup contenders.