Ken Holland’s First Thousand Days

Congrats go out to Ken Holland for making it a thousand days as Oilers GM.

Honestly, can you believe it’s been a thousand days already? Time flies when you’re having fun. All kidding aside, being GM of the Oilers is a tough gig. The market is ravenous, the fans are tough but fair. If the Oilers are winners, you get all the accolades. If they stink, you’re going to get the horns.

Holland was brought in at the conclusion of the 2018-19 NHL season. As with any GM new on the job, there’s always some tidying up from the last GM, and Ken Holland was no exception. Peter Chiarelli didn’t exactly leave Ken Holland an easy task, but the core of the team was easily identifiable. Holland had a couple of contracts that he would have to rid himself of, and there’s that pesky job of actually making the team better in the process.

Now we’re a thousand days into his tenure, and I think it’s a fair time to take stock and assess how the Hall of Fame GM has done during his time in Edmonton.

I’m critical of Ken Holland’s work, but I’d like to believe that I’m fair. It’s not easy being a general manager in the NHL, it’s even tougher being a good general manager. Like most GMs, Ken Holland has had some very good moments, and he’s had some moments he’d probably like to forget. The trick is to have way more good moments than the ones you’d like to forget.

With all of that in mind, let’s take a quick look back at some of Ken Holland’s moments with the Oilers.

THE BEST

Ken Holland deserves full marks for mending the fences with Jesse Puljujärvi.

Jesse Puljujärvi was the fourth overall selection in the 2016 NHL Entry Draft, he broke camp with the club and scored 20 points in his rookie season. What should have been a time for development was a time fraught with instability and outright recklessness from management. Puljujärvi could have benefitted from significant time in the AHL to develop, he often was on a line with Milan Lucic while in Edmonton, or scratched altogether. He ended up playing in a paltry 53 AHL games over the course of three seasons. Language became a barrier. Things were spiraling out of control between Puljujärvi and the club. A double hip surgery at the conclusion of the 2019-20 season and a trade request from his agent looked like the end of his time with the Oilers. But, it wasn’t.

Puljujärvi would spend a season with Liiga, which would help rekindle his confidence. While playing in Liiga, Ken Holland did his best work since becoming GM of the Oilers: he got Puljujärvi to sign for under 1.2MM a year for two years. It was a super bet for Holland, it continues to be great value for the Oilers today. Puljujärvi’s confidence was through the roof when he returned to the club, he’s quickly shown that he can be that big body net-front presence that the Oilers sorely needed. Though currently in a scoring slump, Puljujärvi is tied for his career high point total with half a season remaining. Now a contract year for Puljujärvi, he’s a player that the Oilers should prioritize prior to free agency.

THE GOOD

Ken Holland had an albatross of a contract in Milan Lucic when he first arrived in Edmonton. Former GM Peter Chiarelli inked Milan Lucic to a nearly bulletproof seven year contract at six million per year back in 2016. It came with a full NMC, which made moving that contract nearly impossible. Because the deal was laden with bonuses, it was impossible to buy out without Edmonton absorbing over 75% of the cap hit.

Lucic’s heyday was in Boston where his crash and bang play combined with a scoring touch. Twice a 60 point scorer, it was too much for Peter Chiarelli to stay away from when he signed the big man to a seven year deal. After a successful 2016-17 campaign that saw Lucic score the lion’s share of his 50 points on the power play, his point total dove off a cliff. Lucic had a 29 game stretch without a goal (0-5-5) between December of 2017 and March of 2018. Things had dried up, and they dried up quick.

Ken Holland was able to get Lucic to waive his NMC and take a deal to Calgary for James Neal. The Oilers would end up holding 15% of Lucic’s cap hit, but the Oilers were winners this day if for no other reason than they could buy out James Neal’s contract if they needed to.

After two years, the Oilers bought out James Neal’s contract, and saved nearly four million in cap space for this year and next. What would they end up doing with that cap space? Funny you asked.

MAX CONTRACTS

Someone smarter than me once said that bridge contracts take you to bigger contracts, and that person was right. Holland gave Darnell Nurse a bridge deal for two years at 5.6MM a season back in 2020. With Oscar Klefbom likely never playing another game for the Oilers, Darnell Nurse is the club’s number one defenceman. With Nurse about to embark on his second year of the bridge, Holland offered Nurse a maximum contract at 9.25MM a year, which will keep Nurse in Oiler colours until the end of the 2029-30 season. The deal contains a full NMC until 2027, when the deal becomes modified to a 10 team NTC. Nurse is the club’s number one defenceman today, and he’s had a better year defensively than years previous, but that length and term is a gamble.

NOT SO HOT

Ken Holland’s 2021 end of season press conference heard him say that the Oilers needed more “greybeards” in the lineup. Holland was alluding to veteran presence, and he wasted almost zero time trading for Chicago’s Duncan Keith in what is probably his worst move since becoming GM. At 38 years of age, Keith was well into the twilight of his NHL playing career, but that didn’t stop Ken Holland from trading Caleb Jones and a third (potential to become a second) round pick to Chicago for Keith and Tim Söderlund. 100% of Duncan Keith’s 5.5MM cap hit was taken on by Ken Holland, and it’s pretty clear that Keith is best suited for third pair minutes at this point of his career. It’s a bullet to Edmonton’s cap space even if you like the player. Duncan Keith is signed through the 2022-23 NHL season. Chicago used the cap space to acquire Marc-Andre Fleury from the Vegas Golden Knights.

Tim Söderlund’s contract was recently terminated.

A HEAD SCRATCHER

One of Holland’s biggest disappointments in his first thousand days on the job is his inability to shore up the goaltending. Since becoming GM, he’s signed Mike Smith three times, and that’s where it starts and stops. Smith signed a one year deal with the Oilers in 2019-20, another year in 2020-21, and a two year deal before the start of this season. A big issue? Mike Smith is about to turn 40 in a month. Smith had a good campaign in 2020-21 when he finished with a very lovely .923 SV% over 32 games. He had a sub .900 campaign in 2019-20, and he hasn’t been able to stay healthy this year for more than a few games at a time. With Mikko Koskinen a pending UFA and Stuart Skinner with just 13 career games to his name, the goaltending is an especially volitile position almost three full years into Ken Holland’s tenure as Oilers GM.

ANOTHER HEAD SCRATCHER

Back in 2020, the Oilers handed Zack Kassian a four year deal valued at 3.2MM a year. Kassian will remain an Oiler until the 2023-24 season ends. Even though Ken Holland found a dancer for Milan Lucic, I don’t know how he’s going to find a club to take a full ride on Kassian’s remaining time. Kassian was playing on the McDavid line in 2019-20 and was shooting well over 15% on the season. It’s clear as day that Kassian was on a heater, but that didn’t stop Ken Holland from awarding a four year deal at 3.2MM a year. He’d finish 2019-20 with 34 points, the most in his career. Since then, he’s scored a grand total of 19 points. I don’t look at Kassian as being a big goal scorer, but he’s got to be able to agitate his opposition if he’s going to be effective. It’s not happening right now, and the Oilers are not better off for it.

SEVERAL SMALLER HEAD SCRATCHERS

Mike Smith’s additional 2.2MM could be a problem if the Oilers are as close to the cap next year as they are right now. There’s a handful of players on the roster that were unnecessarily signed to multiple year deals that haven’t worked out. Kyle Turris got a two year deal prior to the 2020-21 season. Devin Shore signed a two year deal last summer. Ditto Slater Koekkoek. These deals aren’t particularly big cap killers, but Dave Tippett will play Devin Shore until he can’t any more. The Oilers waived Slater Koekkoek today. Kyle Turris hasn’t panned out. I’m not including the latest Tyson Barrie deal where he got three years, as that was a completely different set of circumstances. But the fringe guys? Why do they get multiple years?

ETC

I’ve been critical of Ken Holland’s first thousand days on the job for many reasons, but the biggest one is pretty clear: This club doesn’t appear to be any closer to being a real threat in the playoffs than they were when he first got the gig. I’ve left out a handful of deals like the recently signed Evander Kane deal, the first contract Tyson Barrie signed with the Oilers (which was a good bet), the Cody Ceci deal (has shown well, but four years is too long), and a few others.

All of these deals (with the exception of Mikko Koskinen) are Holland’s work. This is his club. Halfway through the 2021-22 campaign, the Oilers are a little bit better than a coin flip to get into the playoffs this season.

The club has one playoff appearance in Holland’s tenure with Edmonton (two if you count the play-in series from which they were defeated by a twelfth place Blackhawks club) and zero series wins. Ken Holland’s first 1000 days have seen plenty of spinning wheels, but the Oilers have yet to really get anywhere. We are in year 7 of Connor McDavid and year 8 of Leon Draisaitl, and I feel the club is no closer to a series win compared to when Holland came on board.

With the Oilers being up against the cap, having signifcant question marks in goal after this season, a shaky defence corps and a bottom six that contains a lot of fringe NHLers on multiple year deals, Ken Holland will need to defy some odds in order to make his next 1000 days a smoother ride than his first 1000.