Perhaps the Islanders almost acquired Max Pacioretty after the Kings almost did

At last weekend’s NHL draft, the New York Islanders nearly acquired disgruntled Montreal Canadiens left wing Max Pacioretty.

Such is the report from Eric Engels, who covers the Canadiens closely for Sportsnet:

We know getting either Bergevin or New York Islanders GM Lou Lamoriello to admit that they had a potential deal worked out that would’ve seen Pacioretty going one way and either the 11th or 12th overall pick going the other would be akin to asking Donald Trump to admit to a lie, but that doesn’t mean it didn’t happen.

But Engels laid out the case for how and why this could have happened, including a third team where Montreal would have flipped the Islanders’ first-round pick to the Sabres for Ryan O’Reilly:

It would’ve been a win for all parties involved, with Bergevin trading Pacioretty and landing O’Reilly after drafting a potential future No. 1 centre in Jesperi Kotkaniemi; with Pacioretty moving to a destination of choice, signing a long-term contract extension and being guaranteed a chance to play with an elite centreman (Mat Barzal or John Tavares) for years to come; with Lamoriello netting a proven 30-goal scorer/one more piece to help him convince his franchise player (Tavares) to skirt unrestricted free agency in favour of a return to the Islanders...

It’s unclear where the “we’re told the deal was on the table” leak is coming from — you might bet on the Canadiens (to explain to their fans “WE ALMOST ENDED THIS DRAMA AND ALMOST GOT O’REILLY, GUYS”), or possibly Pacioretty’s former or current agent, or it could be a league source if talks progressed to that point. (“Deal was on the table” is also vague enough to not mean that all parties were agreed on conditions.)

Why Pacioretty?

He’s a regular 30-goal scorer coming off a bad year and feeling unloved by the Canadiens. He’s also entering the final year of a contract that immediately looked like a bad underpay for him soon after it was signed. He fired the agent who negotiated that contract, and then this past week he fired Pat Brisson, who is also conducting the John Tavares Decision out in L.A.

Elliotte Friedman touched on this dynamic in his 31 Thoughts, noting that a proposed trade to the Kings at the draft was vetoed by Pacioretty, who wouldn’t sign the proposed extension and then switched from Brisson to Agent Allan Walsh:

I do believe he would like to play in Los Angeles, but would also like to make up for what he left on the table with the Canadiens. LA can’t fit that. Pacioretty is upset and the Canadiens are upset, so even though word was they may keep him now, that’s going to be awkward if it happens.

Arpon Basu and Marc Antoine Godin recently had more on this dynamic in a piece for The Athletic examining the Pacioretty-Bergevin breakdown:

That contract was negotiated by Pacioretty’s first agent, Alec Schall, and 14 months later Pacioretty fired him and hired Pat Brisson and CAA. At that point, in November of 2013, he was in the midst of a career-best 39-goal season. From the beginning of that season to the end of 2016-17, Pacioretty was one of the best goal scorers in the NHL.

But he wasn’t paid like one.

[...]

According to multiple sources, but not Pacioretty himself, the relationship between Bergevin and [he and Tavares’ agent Pat] Brisson had planted a seed of doubt in Pacioretty’s mind about the ability of his agent to adequately represent his own best interests. Like he was an afterthought. It was a sense that could have been reinforced by the fact Brisson is knee deep in the John Tavares situation, managing what could be the biggest free agent in NHL history. Maybe in that context getting Pacioretty the best possible contract was not the top priority for his agent.

So Pacioretty turned to Walsh, the agent of his good friend Jonathan Drouin, and in so doing killed two birds with one stone.

Piecing all of these reports together, the timeline would suggest that a trade to the Kings before the draft fell through because the Kings couldn’t give him the contract extension he felt he deserved...but then Pacioretty was agreeable to a trade (and presumably a larger extension) to the Islanders.

Except (according to the implication in Engels’ report) Lou Lamoriello didn’t pull the trigger when Oliver Wahlstrom and Noah Dobson both fell to the Islanders in the draft (“once the picks started rolling in”). Then, Pacioretty fired his agent.

Would You Do The Deal?

Frankly, as much as I like Pacioretty as a player, I’m not interested in giving up assets to then sign him for a long-term extension (starting in 2019-20) that overpays him in his aging years to make up for the underpayment of his prime years spent with the Canadiens.

After four straight 30-goal seasons, Pacioretty dropped to 17 goals in 64 games in 2017-18. Granted, Montreal was a mess and management and media looked almost like they were trying to antagonize him all season, but Pacioretty turns 30 in November of this coming season, the final year of his contract. The Isles, meanwhile, don’t exactly have a dearth of top-six wingers.

If these were the conditions of the offer “on the table,” I’m glad Lou passed.