Grading Ken Holland’s 2023 Off-Season

As we inch ever so closely to the 2023-24 regular season (and I do mean inch, for the hockey-crazed amongst us), it’s a good time to take a retrospective look at the Oilers' most recent off-season and summarize the major moves that have taken place over the past four months.

June 13, 2023

Derek Ryan re-signs for 2 years @ $900K AAV

Let's kick things off with a no-brainer. Shortly after the off-season begins, Derek Ryan signs on for two more years at a steal of a deal - $900K. Coming off another multi-digit goal season, Ryan’s chemistry with Warren Foegele and Ryan McLeod was a rare bright spot in an otherwise disappointing 2023 playoffs, reminding Oilers fans that it is indeed possible for the team to outscore their opponents at 5v5 without McDavid and Draisaitl on the ice. Ryan’s defensive reliability and penalty-killing prowess will continue to be a vital part of the Oilers bottom-6, and will come at a price that's easy to bury in the AHL if the wheels do fall off. Some folks may squabble about the second year, but if that’s what brought the cap hit down, it’s a smart bet in my books.

Grade: A

June 29, 2023

EDM sends Kailer Yamamoto & Klim Kostin to DET for Future Considerations

It’s the early hours of Draft Day Two and Friedman drops a bombshell. In a cap-clearing measure, Holland will be sending (or more appropriately, giving away) Klim Kostin & Kailer Yamamoto to the Detroit Red Wings. Although it was easy to predict that Kailer Yamamoto would be an offseason casualty, Kostin was a different story. He had quickly risen the ranks in Oilers fandom due to his outspoken personality, media antics and clutch scoring. Although most were envisioning his return in orange & blue, it seems Kostin had other plans, and with his agent reportedly threatening a move to the KHL, the Oilers were unable to squeeze him into the cap puzzle. 

In retrospect, it's clear Kostin was looking for more than the Oilers could afford. With that in mind, Ken Holland was able to solve two problems in one maneuver—capturing Kostin's RFA value while shedding Yamamoto's cap-heavy contract. It was likely the most heart-wrenching move of the offseason for many of us in Oil Country, but it’s one that makes sense when considering team financials and roster construction. The Oilers could not afford another $2M+ bottom-6 winger. Perhaps, in time, Kostin will prove us all wrong for not taking a chance on him. Perhaps Yamamoto will as well.

Grade: B

July 1, 2023

Connor Brown signs in EDM for 1 year @ $750K (plus an additional $3.25M in perf. bonuses)

A few short hours after NHL Free Agency opens, the Oilers make their first big signing. While Oilers fans are exceeding their rate limit on Twitter, Brown is inking a 1-year, league min, performance laden deal with Edmonton, thanks to a nifty CBA loophole. Although this move had been telegraphed for weeks, Holland & co deserve kudos for getting it across the finish line, especially when considering there were upwards of 12-16 teams vying for Brown’s services.

Brown’s history with McDavid is well-documented, and he'll be relied upon both at 5v5 and on the penalty kill. It may take him a while to get back up to speed, but the numbers indicate he should fare better than his predecessors. At $750K for the coming season, that is a steal and a half.

My only reservation with this deal is that I wish Holland had penny-pinched a bit more on the bonus conditions. Brown will easily hit the 10 GP minimum to cash out on his bonuses, and the $3M he’ll receive will likely eat a sizeable chunk of next year’s cap. In a summer where the league’s cap ceiling is projected to increase by upwards of $5M+, it would have been nice to see the Oilers operating with more flexibility. Nevertheless, this move should make the current iteration of the team much harder to play against, as the players set their sights on a cup in 2024. We wanted Holland to go all-in, and we got it.

Grade: A

August 1, 2023

Ryan McLeod re-signs for 2 years @ $2.1M AAV

The calendar turns to August, and after a month-long standoff, the Oilers are able to avoid arbitration and ink McLeod to a 2-year deal. In an ideal world, we would have seen the number drop below the 2-million-dollar mark, but after seeing similar-caliber players cashing in at higher rates, it’s evident that even a penny less may have been wishful thinking. Coming off an 11-goal, 23-point season, McLeod will need to take another step this year if the Oilers hope to be true contenders. No pressure, Ryan.

Grade: B

August 24, 2023

Evan Bouchard re-signs for 2 years @ $3.9M AAV

To cap off a busy summer, the Oilers finally lock down their golden goose at a sub-$4M cap hit, albeit for only 2 years. Bouchard will be quarterbacking the league's best power play for the next two seasons, and you can bet your house he'll be demanding a hefty raise in 2025 (the same year Draisaitl needs a new contract, mind you). Two years might have been the only card to play, but I would have loved to see some cap gymnastics or creativity to add extra term to that contract. And really, it's hard to let Holland off the hook for a situation that he helped create.

Grade: C

September 2023 

Oilers Sign Gagner, Sutter, Erne to PTOs

Lastly, we've got the camp additions. While these types of deals don’t make headlines (except in hockey-starved markets like Edmonton), they’re the mark of a successful, proactive team. Gone are the days of handing rookies roster spots. If Raphael Lavoie wants to make the team, it will be on merit, and these PTOs should set the stage for some fierce competition.

Grade: N/A

There you have it, folks—a breakdown of Ken Holland's summer, or at least a large chunk of it (as you may have noticed, a few of the smaller moves have been omitted). The Oilers are heading into the new season with an improved starting lineup, but Holland’s work is far from over. Expect the team to make at least one more impactful move sometime mid-season. With that being said, let’s gear up for what should be another fun and eventful year ahead.

Thanks as always for reading. Cheers!

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