Edmonton Oilers GM Ken Holland just had a summer fans of the team will never forget. But will we rejoice or retch?

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Edmonton Oilers GM Ken Holland just had a summer that fans of the team will never forget. But in years come will his move make us rejoice or retch?

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Did Holland make wise bets this momentous summer? Or too many reckless gambles?

Holland’s work was nothing short of earth-shattering when it comes to shaping the fortunes of the Oilers for the next decade.

He signed two stalwarts, Ryan Nugent-Hopkins and Darnell Nurse, to eight-year deals.

He signed one major free agent Zach Hyman to a seven-year deal.

He traded promising young d-man Caleb Jones and Ethan Bear for an aging Hall-of-Famer in Duncan Keith and a solid third line winger in Warren Foegele.

He lost out on Adam Larsson and tried to fill that major hole with Tyson Barrie and Cody Ceci.

And he made two crucial bets on two more aging vets, Mike Smith and Derek Ryan.

If the Oilers win one or two Stanley Cups in the last five years of Connor McDavid’s eight year contract, maybe we’ll all shout Holland’s name from the rooftops and dance in the streets. But if things go sour, we’ll all be pointing at the moves he made in June and July 2021.

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In rating Holland’s work, it’s best to ask some simple questions: over the lifetime of the new acquisition’s contract with the Oilers, will the deal prove to be a solid one for the Oilers? Will it be seen as a win?

The higher the percentage odds are that this will happen, the better the bet that Holland has made.

For example, when the Oilers signed Connor McDavid to an eight-year deal, I would have given that about a 95 per cent chance of working out, the only issue being whether or not McDavid would stay healthy through the length of the long-term deal.

At the other end, the Milan Lucic signing had about a 50/50 chance of working out. Lucic had one near peak season in Edmonton, then two dismal ones, after which he was traded for James Neal, so that deal was nowhere close to a win for the Oilers.

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In fact, the Decade of Darkness was marked by numerous reckless gambles that were at best 50/50 propositions, and many of them worse than that.

As for Holland this summer, here’s my take:

  • 80%. The Devin Shore contract, two years at $850,000 per. Why such a high chance of success for such an iffy fourth line player? Because I’d say the same about almost any player signed for this amount. What’s the downside if he fails? He gets sent to the minors, there’s no penalty against the salary cap. What’s the upside if he succeeds? The Oilers have a useful bottom line player. In the next month, Holland should make a few more bets just like this one.
  • 60%. The Ryan Nugent-Hopkins contract, eight years at $5.125 million per. If Edmonton wins a Cup or two in the next few years, and RNH is a key contributor, this bet will have paid off, even if RNH fades badly in the last few years of this deal, as is likely.
  • 50%. The Duncan Keith for Caleb Jones trade. This pays off if Keith helps solidify the Oil’s defence for the next two season and plays well in the playoffs. It fails if Keith fails and/or if Caleb Jones turns out to be a Top 4 NHL d-man for four or five seasons.
  • 70%. The Mike Smith contract, two years at $2.2 million. Smith just had a great season at age 38, an indicator he’s got a decent shot at joining that rare club of NHL goalies who play well into their early 40s. If he does take a step back, he’s not paid so much that the contract is a disaster.
  • 60%. The Tyson Barrie contract, three years at $4.5 million. We can count on Barrie to be a solid puck-mover and power play ace for three more years, but can we count on him to provide solid and winning defensive play in the playoffs? That’s where this contract could easily go sideways.
  • 60%. The Zach Hyman contract, seven years, $5.5 million per. Same comment as with RNH. If he helps Edmonton win a Cup or two, this deal will have worked out, even if he fades in the last half of the deal.
  • 60%. The Ethan Bear for Warren Foegele trade. The Oilers turned a surplus of puck-moving right-shot d-men into a useful winger in Foegele, addressing a need on the team. That’s sharp dealing by Holland, but if Bear turns out to be a Top 4 d-man for the next four or five years, this trade will be seen as a fail.
  • 66%. The Warren Foegele contract, three years at 2.75 million per. He’s in the prime of his career and he’s a decent winger, so this contract is more likely than not to work out for the Oilers.
  • 33%. The Cody Ceci contract. four years at $3.25 million. Too much term and money for a player who’s never crushed it as a Top 4 d-man in the NHL. But maybe he’ll surprise us all.
  • 66%. The Derek Ryan contract, two years at $1.25 million. Another inexpensive bet, but the blowback will be significant if Ryan can’t cut it, as he’s in a key position, third-line centre.
  • 66%. The Darnell Nurse contract, eight years, $9.25 million per. Who else would the Oilers get as a No. 1 d-man over the next five years, if not Nurse? He’s a strong attacker, but needs to improve his reads and consistency as a shut-down d-man. The good news is he’s improved every year he’s been in the NHL, making him a good bet to continue to get better. Of course, the consequences of him failing to improve or fading are immense. But I would not bet heavily against Nurse. He’s consistently exceeded expectations.

At the Cult

McCURDY: Nurse signs

STAPLES: Edmonton Oilers need to be careful to avoid a Karlsson/Doughty overpay with Darnell Nurse, NHL insider suggests

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