After the Oilers won the Golden Ticket at the 2015 Draft Lottery, they brought Peter Chiarelli on board to help guide the franchise to success. He was a seasoned, veteran general manager who had the pedigree of winning a Stanley Cup in Boston and he was a much-welcomed breath of fresh air from the Old Boys Club who had unsuccessfully managed the organization for many years prior.

To be blunt, it didn’t go as planned. He created many cracks and holes on the ship that led to the Oilers sinking. He was fired three-and-a-half years into his tenure and the Oilers are now back at square one. This time, rather than finding somebody to steer a ship loaded with prospects and financial freedom to success, the Oilers need to find somebody to clean up the wreck left by Chiarelli.

The situation

On the bright side, the Oilers still have a nice core of Connor McDavid, Leon Draisaitl, Ryan Nugent-Hopkins, Oscar Klefbom, Darnell Nurse, and Adam Larsson under control for at least two more years after this one. Of course, on the not-so-bright side, the Oilers have a wealth of bad contracts bogging them down, making it difficult to add to that solid core. Also, Chiarelli managed to lose value in so many deals that the Oilers now lack high-quality depth.

Advertisement - Continue Reading Below

So while Edmonton has a core featuring the best player in the league to build around, the next general manager brought in will have to navigate through salary cap hell while also accumulating talent up and down the roster.

The last thing Oilers fans — who have endured many years of tanking, coaching and management changes, and failed rebuilds — want to hear is be patient. Unfortunately, there aren’t any quick fixes. Patience is what it’s going to take to turn this ship around.

Navigating cap hell

The biggest issue for whoever takes over is going to be navigating the Oilers out of cap hell. The Oilers already have the majority of their roster intact for the 2019-20 season and it’s going to take some time to push out the bad contracts weighing this team down.

Assuming Kailer Yamamoto and Evan Bouchard are on the team, the Oilers have eight forwards, eight defencemen, and one goalie combining for roughly $72 million against the salary cap. RFAs Jesse Puljujarvi and Jujhar Khaira will be back with new contracts, while Ty Rattie and Tobias Reider might not. Ryan Spooner and Brandon Manning could be buried, which would save just over $2 million. Regardless, the Oilers don’t have much wiggle room.

Advertisement - Continue Reading Below

Some of Chiarelli’s most puzzling moves came in the final few months before he got fired. He turned two serviceable forwards, Ryan Strome and Drake Caggiula, into two players who are best served as buried contracts in the AHL, Ryan Spooner and Brandon Manning. He also inked Mikko Koskinen, a goalie with virtually zero track record of success at the NHL level, to a fairly big contract.

These are the death by a thousand papercuts moves that highlighted Chiarelli’s tenure as Oilers general manager. Out went two decent players, in came roughly $3 million in dead cap room. The Koskinen deal may end up being fine if he plays as he did in his first two-dozen games with the Oilers, but if he doesn’t, he’ll end up being added to the list of problematic contracts along with Milan Lucic, Andrej Sekera, and Kris Russell.

Ideally, the Oilers could trade Spooner and Manning without taking anything back in return. I can’t imagine anyone is lining up to take on those cap hits, though. They could also buy both players out, putting them on top of the charges they have for getting rid of Benoit Pouliot and Eric Gryba. It would cost $1,333,333 over two seasons to buy out Spooner and it would cost $916,667 and $666,667 over the next two years to buy out Manning. It’s best just to bite the bullet with these players as their deals expire after the 2019-20 season.

The other problematic contracts aren’t going anywhere soon. The biggest one, of course, is the Milan Lucic deal. There are four more years left after this one and it’s been structured to be buyout proof. Andrej Sekera may or may not be a problem. He’s got two more years left at $5.5 million and we have no idea what to expect from him coming off his second major injury. Putting Kris Russell in this category is probably a bit unfair. He’s a solid player, and while $4 million is a little rich, you can do a lot worse. Koskinen, as I said earlier, could also end up in this category too. All the Oilers can do is hope he’s the goalie he was earlier in the season.

The key to working through salary cap hell is patience. If the Oilers had a Stanley Cup window open right now, you could validate things like using draft picks and prospects to dump bad contracts and buyouts to spread deals over a longer period of time. But the Oilers are back into somewhat of a rebuilding phase, so the best thing to do is let these things ride out rather than trying to look for a quick and easy solution with long-term ramifications.

Finding talent

The other part of navigating salary cap hell involves being conservative when it comes to talent acquisition. The Oilers are badly lacking high-quality depth on their roster at this stage, but given their situation, they can’t go nuts in free agency to solve their problems.

Advertisement - Continue Reading Below

The bright side is that there’s already a foundation here to build around. Beyond the talent like McDavid, Draisaitl, and Klefbom already on the roster, the Oilers have some interesting young players working their way up the system.

Evan Bouchard looked good during his cup of coffee at the NHL at the beginning of the season and Caleb Jones was better during his call-up than anybody could have expected. The AHL team in Bakersfield, led by young talents like Cooper Marody, Tyler Benson, Jones, and William Lagesson, is currently on a 12-game winning streak. Michael McLeod, Krill Maksimov, and Ostaf Safin are next in line to join the Condors as the older players graduate to the NHL level.

As the Oilers slowly work their way out of salary cap hell, they need to shift their focus to loading the system with talent. On one hand, they’re only a few points out of a playoff spot right now, on the other hand, they’re only a few points up on dead last in the league. I’m not suggesting the Oilers go on a tankathon as we saw in the early 2010s, but the priority right now can’t be loading up for a short-term run.

Accumulating talent goes hand in hand with working out of cap hell. The key is patience and making decisions that benefit the long-term health of the organization. It’s better to deal Alex Chiasson, Alex Petrovic, Kevin Gravel, Cam Talbot, and whoever else on short-term deals at the deadline than it is to give up draft picks and prospects to make a run at making the playoffs.

It’s the same deal next year too. The top priorities right now are shedding dead weight and adding to the system. Maybe the team can squeeze into the playoffs with what they already have, but the goal shouldn’t be to make additions, whether through trade or free agency, that simply put a bandaid over the wound.

Advertisement - Continue Reading Below

What does it all mean?

It’s easy to be frustrated about where the organization is standing right now. I mean, it’s impossible not to be. Nobody expected back when the Oilers won the lottery that this is where they would be four years into McDavid’s NHL career. The organization is worse off after three-and-a-half years of Peter Chiarelli than it was when they hired him.

Unfortunately, the only way through this mess is patience. The Oilers have two major issues to fix due to the Chiarelli era. They’re deep in salary cap hell and they lack high-quality depth. You can’t quickly work out of salary cap hell and, if you’re in salary cap hell, you can’t just go on a shopping spree to acquire quality depth.

Chiarelli made a lot of mistakes during his time here, obviously. I think the biggest issue, though, was haste to make changes. He came in and quickly spent the open salary cap room he had on free agents and dealt away high-quality assets to fill holes. Had he taken the time to allow the young team to figure itself out, things could have gone a lot differently.

If the next general manager comes in and tries to remedy the Oilers with a quick fix, things will only get worse. Buyouts will worsen the cap situation long-term. Trading prospects and draft picks for short-term solutions will continue to hemorrhage the organization of depth. Being active in free agency will sink the Oilers deeper into cap hell.

The only solution is patience. It’ll take time, but they have to get it right this time.



