Ken Holland's Best & Worst Signings With the Edmonton Oilers

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NHL free agent frenzy is about to begin, and Ken Holland has around $20m in cap space to work with going into a crucial off-season for the Edmonton Oilers.

Free-agent day is sometimes referred to as a day where mistakes are made more often than not. And while that may be true, that is simply the risk you have to take in order to make your team better, this applies to the Edmonton Oilers this offseason.

This year boasts an impressive crop of free agents that will include Evgeni Malkin, Evander Kane, Claude Giroux, Jack Campbell, Darcy Kuemper, and possibly even Johnny Gaudreau. With the big day looming, I will be taking a walk down memory lane to see what Ken Holland’s successes and failures have looked like with the Oilers so far in terms of the contracts he has signed.

3 Best Contracts:

Evander Kane – 1 year x $2m (2022)

This past winter, Holland signed arguably one of the best one-year deals in NHL history when he brought in the controversial, but talented Evander Kane for next to nothing. It was probably Kane’s last chance to get things right in the NHL after a slew of bad press and concerns about his off-ice behavior, and what did he do with the opportunity?

He scored 22 goals and had 39 points in 43 regular-season games, and then followed that up with 13 goals in the playoffs, the second-most goals scored by an Oiler in the postseason since the 80’s dynasty (Fernando Pisani had 14 in 2006). An incredible run for Kane alongside Connor McDavid and Leon Draisaitl helped propel the Oilers to the Western Conference final, where they were bested by the eventual Stanley Cup Champion Colorado Avalanche.

While he will likely be leaving Edmonton in free agency, it was quite an incredible year that the Oilers got out of Kane, for a major discount.

Zach Hyman – 7 years x $5.5m (2021)

The signing of Zach Hyman was a bit of a risk – not because he isn’t a fantastic player, but because the term was so long and he has had some injuries in the past. Hyman needed to come out in year one of his contract and prove that he is worth the money and the commitment the Oilers made.

In the first season of his Oilers tenure, Hyman set career highs in goals, assists, and points in both the regular season and playoffs, not too shabby of a start for number 18. This was a good move by Holland that made the Oilers a better team, no doubt about it.

Cody Ceci – 4 years x $3.25m (2021)

When Adam Larsson left to join the Seattle Kraken, there was a lot of panic around Oil Country over the loss of their big, physical, stay-at-home D man. The Oilers desperately needed to replace him with a player that could stabilize the right side of the defense group and provide a steady presence.

Ceci was a cheaper option than Larsson, and while the four-year term was questioned by some at first, no one is complaining about this contract now. Ceci was steady for the Oilers, especially in the playoffs, and was arguably the best defensive defenseman on a team that made it to the conference finals. I would give that contract a passing grade for Ken Holland any day.

Edmonton Oilers forward Kyle Turris. Mandatory Credit: Perry Nelson-USA TODAY Sports /

3 Worst Contracts:

Kyle Turris – 2 years x $1.6m

Kyle Turris has never been a strong defender, and his offense had been in consistent decline over the previous few seasons when Ken Holland decided to sign him to a multi-year deal at $1.6m. It’s one thing to bank on a player bouncing back, but when the player has had poor underlying numbers that have only gotten worse every year, and you extend that risk an extra year, that is another thing entirely.

While the $1.6m isn’t a ton of money, you can find decent depth players for cheap, and instead, the Oilers got a player that was in the AHL by the end of the deal. Turris was no doubt a major flop in Edmonton, as he produced some of the worst possession numbers I’ve seen in quite some time, and predictably, failed to recapture any offense.

Zack Kassian – 4 years x $3.2m

Did Zack Kassian produce well during the 2019-20 season when this contract was signed? Yes. Were there also numerous warning signs that a four-year deal at over $3m was a bad idea? Also yes. Kassian’s offensive numbers were not only inflated by playing almost a full season next to Connor McDavid, but also a red-hot shooting percentage of 16.67%.

This shooting percentage was a major outlier to his usual shooting of closer to 10%, and for a guy that has been in the bottom six for most of his career, this should have set off warning signals that Kassian’s success just wasn’t sustainable. I understand that the team was extremely thin on scoring wingers at the time of this contract, but Holland signed it in the middle of the season with absolutely no pressure to get the deal done.

He probably should have waited to extend Kassian to see if there were any better replacements on the market. While Zack Kassian will be remembered fondly by many for his physical brand of hockey, the term and money were both far too much on this deal, and the Oilers had to spend assets just 2 years later to get rid of that cap.

Darnell Nurse – 8 years x $9.25m

The Darnell Nurse contract is another cautionary tale of extending a player after a career year where they had an unsustainably high shooting percentage that inflated their production. I understand that the Seth Jones deal completely broke the market for number one defenseman, and all of the big names were being signed to monster contracts that summer, but the Oilers could have easily waited until the next season to sign Nurse.

There is just no way that his value could have gone up again to the point where he wouldn’t accept a $9.25m deal. There was nowhere for Nurse’s value to go but down, and the Oilers instead elected to lock him up when his value was at an all-time high. I will say that Darnell Nurse is still an elite offensive defenseman, whose defensive woes are overblown by many in the fanbase that don’t like his contract.

He is the Oilers’ best defenseman, but let’s be honest, the fact that he makes more money than Cale Makar is insane. His true value is probably somewhere closer to the $7m range that Morgan Reilly signed for just one year after Nurse, and that extra cash could have come in handy for the Oilers this summer.

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