This off-season will be much different than last for Ken Holland and the Edmonton Oilers.

After spending his first two years at the helm cleaning up the mess left by his predecessor, Holland had over $20 million in free salary cap room to put his stamp on the organization last summer. He used it to re-sign Ryan Nugent-Hopkins, Mike Smith, and Tyson Barrie, and he also added Duncan Keith and Warren Foegele via trade and inked Zach Hyman, Cody Ceci, and Derek Ryan in free agency.

It’s a different story this summer, as the Oilers currently only have about $8 million in salary cap room to work with.

While there’s always a focus on adding new players to improve the team, Holland’s top priority this off-season is keeping the band together after the team’s run to the Western Conference Final. The Oilers have three good young forwards in need of new deals as restricted free agents along with a pair of mid-season acquisitions who played very well for them set to hit the open market.

Let’s go through the decisions that Holland has ahead of him this off-season…

Under Contract: @Connor McDavid ($12.5M), @Leon Draisaitl ($8.5M), @Zach Hyman ($5.5M), @Ryan Nugent-Hopkins ($5.15M), @Zack Kassian ($3.2M), @Warren Foegele ($2.75M), @Derek Ryan ($1.25M), @Devin Shore ($850k), @Seth Griffith ($765k), @Dylan Holloway (ELC), @Xavier Bourgault (ELC), @Raphael Lavoie (ELC), @Tyler Tullio (ELC), @Carter Savoie (ELC), @Matvei Petrov (ELC), @Noah Philp (ELC), @James Hamblin (ELC).

Restricted Free Agent: @Jesse Puljujarvi, @Kailer Yamamoto, @Ryan McLeod, @Tyler Benson, @Brendan Perlini, @Ostap Safin.

Unrestricted Free Agent: @Evander Kane, @Josh Archibald, @Derick Brassard, @Kyle Turris, @Colton Sceviour, @Brad Malone, @Cooper Marody.

Under Contract: @Darnell Nurse ($9.25M), @Duncan Keith ($5.538M), @Tyson Barrie ($4.5M), @Cody Ceci ($3.25M), @Slater Koekkoek ($925k), @Dmitri Samorukov (775k), @Evan Bouchard (ELC), @Philip Broberg (ELC), @Markus Niemelainen (ELC), @Phil Kemp (ELC), @Michael Kesselring (ELC), @Vincent Desharnais (ELC), @Oscar Klefbom ($4.167M on LTIR).

Restricted Free Agent: @Filip Berglund.

Unrestricted Free Agent: @Brett Kulak, @Kris Russell.

Under Contract: @Mike Smith ($2.2M), @Stuart Skinner ($750k), @Olivier Rodrigue (ELC), @Ryan Fanti (ELC).

UFA: @Mikko Koskinen.

Overseas: Ilya Konovalov’s contract was terminated. He’ll continue in the KHL and the Oilers will retain his NHL rights.

In five of the last six off-seasons, the Oilers have opened salary cap room in the short-term by borrowing from the future. They bought out Lauri Korpikoski in 2016, Benoit Pouliot in 2017, Eric Gryba in 2018, Andrej Sekera in 2019, and James Neal in 2021. They currently have over $4 million of dead money on the books from Neal and Sekera along with salary retention from trading Milan Lucic.

The name that stands out for a buyout is Zack Kassian, who’s halfway through the four-year, $12.8 million deal he inked back in January of 2020. A Kassian buyout would save the Oilers $2,533,333 in 2022-23, $1,333,333 in 2023-24, and cost them $966,667 in the following two seasons after that.

While opening up $2.5 million in salary cap room this summer would certainly help, it’s ultimately just kicking the problem down the road to be dealt with later on. Trading Kassian’s contract would be ideal, even if it involves adding a sweetener, so that the Oilers can finally get out of the issue of having dead money once and for all.

The other contracts that stand out as possible money savers are Tyson Barrie, Warren Foegele, Duncan Keith, and Mike Smith.

Barrie has become redundant on Edmonton’s roster because of Evan Bouchard’s breakthrough and his $4.5 million cap hit is pricey for the third pairing. The same goes for Foegele, a fine player who’s a bit on the expensive side at $2.75 million for what he brings as a bottom-six forward. Unlike Kassian, these two players are more likely to be viewed as assets to other clubs around the league. That said, it might be a challenge to move either player without taking money back.

Following the sweep to the Colorado Avalanche, Smith indicated that this might be the end of the line for him as an NHL goaltender. If that’s the case, the Oilers would have $2.2 million freed up for their pursuit of a goaltender. Many have suggested that Holland should urge Keith to retire, but it’s difficult to see that happening.

Over at The Athletic, Lowetide discussed the benefit of trading away the final year of Oscar Klefbom’s contract, as the defender is almost surely never going to play in the league again.

While the Long-Term Injured Reserve is often talked about as an island to stash players without financial ramifications, it isn’t actually that simple. By using the LTIR, a team is given a bonus pool of money to put them over the salary cap ceiling, so any performance bonuses earned would be in addition to the team already being over the limit, and the bonuses would carry over to the next season.

The Oilers owe $896k in performance bonuses to Bouchard and Ryan McLeod that’ll count against their 2022-23 cap because they were over the cap in 2021-22. Next season, they’re going to have three first-round picks on their roster with performance bonuses in their contract (Evan Bouchard at $850k, Philip Broberg at $850k, and Dylan Holloway at $500k) so the bonus overage would likely be higher next time around.

Klefbom’s contract isn’t a major issue for the 2022-23 season but it creates yet another kicking the problem down the road scenario in which the Oilers could wind up with dead money on the books in the future. Adding a sweetener to trade his contract to a team trying to get above the salary cap floor, such as the Arizona Coyotes, would be a helpful move.

The reason why it’s so important for Holland to open up some salary cap room is because there are multiple players on the Oilers who are set to command raises on their next contract. Ryan McLeod has reached the end of his entry-level contract, Kailer Yamamoto and Jesse Puljujarvi are arbitration eligible, and mid-season additions Evander Kane and Brett Kulak can hit the open market as unrestricted free agents.

Many teams were interested in signing Kane after his contract was terminated by the San Jose Sharks in January and even more teams are going to be interested in signing him after he scored 22 goals in 43 regular-season games and 13 goals in 15 playoff games for the Oilers.

Kane said that the Oilers are the best organization he’s ever played for but money talks and somebody out there will more than likely offer him a deal worth $7 million annually, which is the same average salary he was earning in San Jose. Can the Oilers go that high? Would Kane take less to keep playing with Connor McDavid?

Kulak, who the Oilers acquired at the trade deadline from the Montreal Canadiens, was also a seamless fit. He played 18 games in the regular season, scored eight points, and logged 17:05 per game. Kulak’s on-ice goal differential at even-strength was 16-to-12 in the regular season and 12-to-7 in the playoffs.

There aren’t many good defenders on the open market this summer so Kulak will get a lot of attention from teams who need to add a solid veteran to their blueline. He’s a local product from Edmonton, so the literal hometown discount is a real possibility.

Edmonton’s other UFAs are Josh Archibald, Kyle Turris, Derick Brassard, Colton Sceviour, Brad Malone, Cooper Marody, Kris Russell, and Mikko Koskinen, who reportedly has a deal in Switzerland. Turris and Brassard are surely gone, Marody will likely seek an opportunity elsewhere after being passed over so many times, and the others could return on cheap deals.

And then we have the restricted free agents.

Kailer Yamamoto signed a one-year, show-me deal after a difficult 2021 season and popped off with a career-high 20 goals and 41 points. He’s arbitration eligible this summer and those numbers would net him a hefty one-year salary if it got to that, so the goal here is to lock Yamamoto up for multiple years. The Oilers have Yamamoto under control for three more seasons before he’s UFA eligible so two years makes the most sense right now.

Jesse Puljujarvi is now at the end of the two-year contract he inked after spending one year in Finland to find himself. The results from Puljujarvi have been mixed, as the underlying numbers are phenomenal but the boxcars are somewhat disappointing. Puljujarvi scored 15 goals in 55 games in his first year back with the Oilers and he followed that up in 2021-22 with 14 goals in 65 games.

The Oilers have two more years left of control over the Big Finn, so a one-year, show-me deal is probably the most likely course of action. That said, there’s value to be gained in taking a gamble and signing Puljujarvi for multiple years, including free agent years, and hoping for a breakout.

Ryan McLeod has reached the end of his entry-level deal and has already established himself as an effective bottom-six NHLer. In the playoffs, he showed the upside of a very good third-line centre, one who can go up against high-quality opponents in a defensive role and chip in offensively, much like Jarrett Stoll did for the team in 2006. A two-year deal makes sense for this type of player at this stage of his career and then you start to look long-term after that.

Finally, we have the biggest topic of conversation, the thing that loomed over the Oilers through the entirety of the season and ultimately came unraveled at the end — goaltending.

Holland opted to bring back the Mike Smith and Mikko Koskinen tandem for a third go-around this season and the results were mixed. Smith got hurt early on, missed two months, came back and struggled, missed another month, and came back and appeared to be toast. Smith’s rough play had fans screaming for either Mikko Koskinen, who battled to a .903 save percentage in 45 games, or Stuart Skinner, who impressed with a .913 save percentage in 13 games as a rookie.

But, against all odds, the greybeard found his footing down the stretch. Over the month of April, Smith posted a .951 save percentage in nine games. He carried that into the playoffs, posting a .927 save percentage in the wins over Los Angeles and Calgary. The wheels fell off in the Conference Final, as the Avalanche scored 19 goals on Smith in four games.

Koskinen is out the door and Smith and Skinner are signed next season at about $3 million combined. There’s talk that Smith could opt to retire, which would open up $2.2 million in cap room and also a need for another veteran goaltender to play alongside Skinner.

Darcy Kuemper, Jack Campbell, and Marc-Andre Fleury are the big names on the free agent goalie list. Braden Holtby and Jaroslav Halak are quality veteran options and Ville Husso had a nice run with the St. Louis Blues that could get teams interested.

If the answer isn’t on the open market, it might have to come through a trade. Given Edmonton’s cap constrictions, it wouldn’t be surprising to see Holland pull the trigger on a deal for a goaltender involving one of two aforementioned arbitration-eligible restricted free agents.