I’ll admit, my expectations were ridiculously low coming into the off-season. Yes, the team has cap space and are in a position to position themselves for long-term success. But knowing management’s track record when it comes to assessing the team, identifying talent and their overall approach to managing the salary cap, it’s been hard to get too excited about the possibilities.

Here’s what we know about Ken Holland and the Edmonton Oilers.

• He’s a conservative general manager that lacks the creativity and ruthlessness needed to manage a team salary cap in the modern era.
• He highly values veteran players.
• He’s risk-averse when it comes to young players.
• He has a tendency to reward players for past success rather than potential future success,
• He and his professional scouts have a poor track record when it comes to identifying and acquiring professional-level players.
• He doesn’t integrate analytics into his overall decision-making process.
• There is zero over-sight of his work, no review of past transactions and no desire to improve the overall decision-making process.

It’s these traits that have tempered my expectations of the Oilers and have so far led to the signings of Devon Shore, the mysterious release of Matej Blumel and now the trade for Duncan Keith. And while I do like the signing of Nugent-Hopkins to a long-term deal and some previous transactions like the Puljujärvi deal, Holland is more likely to be wrong than right when applying his approach and building this roster. The Oilers clearly don’t care to be progressive and find new ways to get ahead of their competition. And if they do somehow find some success, I’d expect it to be short-lived.

In regards to Duncan Keith, the Oilers have acquired someone that could very well be a productive player and bring those off-ice intangibles – but what are the chances he can be a $5.5 million player? Just look across the league – teams desperately need players who are on value deals and outperforming their contracts and that’s why the Oilers needed Chicago to retain some of Keith’s salary. Keep in mind too that there are four seasons left with McDavid and Draisailt on the roster. And for two of those seasons, the Oilers are committing over 10% of their cap to Keith and Kassian. (Source: CapFriendly)

Needless to say, the acquisition cost for Keith is far too high and really hampers the Oilers ability to address the other major holes on their roster. The Oilers are the ones taking on the most risk here yet come away from the deal with a larger hit to their cap and are using up a roster spot for a relatively unknown prospect who hasn’t shown a lot of progress. Plus they now have to protect Keith in the upcoming expansion draft. Chicago on the other hand gained some much needed cap-space, shed a contract for a stalled prospect, added a third-round (potentially second-round) draft pick and added a prospect who has been progressing well. Chicago came into the negotiation with zero leverage, absolutely none with their backs up against the wall, yet came away as the clear-cut winners. Just embarrassingly poor asset management by the Oilers, but quite aligned with Holland’s previous transactions.

Again though, we know who Holland was before he got to Edmonton. And we’ve seen through his transactions over the past two years what he’s all about. This is what the Edmonton Oilers wanted and they paid him a pretty hefty salary to apply his approach. And so far, they’re getting exactly what they paid for. So let’s not forget the role the owner is playing here and the role CEO Bob Nicholson is playing here. They can talk a big game about building a long-term winner, but until they figure out what it takes to compete in the modern era and are willing to be open to new ideas, they’ll just continue floundering in mediocrity.