Photo Credit: © Tom Szczerbowski-USA TODAY Sports

The Pros and Cons of Picking Your Spots

A long time ago, in the heydays of the great Analytics War, Dimitri Filipovich posed what is still perhaps the most simplistic and yet most illuminating blueprint for success as an NHL General Manager: Identify the dumb GMs and call them every day.

It’s the type of quote that is so confoundingly accurate, it leads you to scream “why didn’t I think of that first?!” into a mirror whilst questioning your own competence.

In the years following Filipovich’s initial words of wisdom, sifting out which GMs happen to abide by this code has become abundantly easy. Pretty much anyone who thought to pick up the phone and talk trades with the Peter-Chiarelli-led Edmonton Oilers sure got the memo. Ditto for any owners of a cellular device with Jim Benning’s name on speed dial. The NHL is a cutthroat business, after all, and picking off the weakest of the pack in order to stay alive is simply par for the course.

This strategy does not seem likely to go away any time soon. In fact, over the past week or so, numerous GMs have made strides to stake their claim for membership on the Dumb List™.

Chuck Fletcher seems particularly hellbent on earning his spot, effectively throwing away a 5th round draft pick last week to acquire the signing rights to Kevin Hayes, a free agent he could have otherwise signed for free on July 1st; trading Radko Gudas, who is a good defenceman, to the Washington Capitals in exchange for Matt Niskanen, who is a worse and more expensive defenceman; then following that all up by dealing two mid-round draft picks to the San Jose Sharks for a package including Justin Braun, his negative possession metrics, and his $3.8 million cap hit.

Now that’s what I call a hot week.

Of course, Fletcher is not the only GM in contention for the Dumb List™. Kevin Cheveldayoff sent his prized asset, Jacob Trouba, to the Rangers just last night for a first-round pick HE ORIGINALLY OWNED and a 23-year-old blueliner with a career-high 5v5 CF/60 of 43.9%. Then there’s Stan Bowman, he of Panarin-for-Saad fame (and two Stanley Cups, but that was a long time ago and a lot less fun to mention), who surrendered a decent winger in Dominik Kahun and a 5th rounder in this year’s draft to Pittsburgh in exchange for Olli Maatta.

Maatta, for those who have not tracked his recent progress, has played a full 82 regular season games just once throughout his six-year career while declining to post a positive Corsi% rel mark since 2015. For reference, David Clarkson was in the Maple Leafs’ top-six in 2015. That was a long time ago.

Case in point; mistakes are being made at a dizzying rate at the moment, which may appear to present the perfect opening for a smart general manager – Kyle Dubas, for example –  to leap in and take advantage. But Dubas has been quizzically silent on the trade front thus far, save for his Fedor Gordeev blockbuster in late May.

Is this the right approach? Good question! Let’s take a look at the pros and cons.


This offseason for the Maple Leafs will be characterized as one of immense change. It has to be, frankly, given how the team’s season came to a disappointing end in both this past April and the April before it.

Changes are an expected and necessary development for the Leafs to move forward. And with fundamental flaws littered all throughout Toronto’s roster, Dubas, being the gung-ho executive that he is, will assuredly do everything in his power to address them.

The main point of contention here, however, is that the offseason has already begun.

We’ve officially entered into peak crazy season, my friends. Teams are losing their minds at an earlier rate than ever before, well in advance of Friday’s draft, which naturally means that a handful of assumed solutions to the Leafs’ problems are quickly being pucked off the table – Gudas being the most heartbreaking of the bunch.

So, why wait? This is a rare moment when Insiders are anointing the likes of Rasmus Ristolainen as the most coveted blueline chip on the current trade market, while also suggesting that, were they the Sabres, the required starting point for a conversation to even begin would need to be Mikhail Sergachev.

Did you read that sentence? Like, in its entirety? Sergachev would be the starting point. As in the same Sergachev who will turn 21 next week, has scored to the tune of 0.48 points-per-game across his first and only two full NHL seasons and is under contract to the cap-strapped Lightning at just $894,166 through 2019-20.

If Sergachev is what it takes to even mention Ristolainen’s name, just imagine the chest of riches Dubas could amass for his own Russian-born right-shot defender, cap gymnastics be damned.

Justin Braun, for example, scored at nearly the exact same pace Zaitsev did last season (16 points to Zaitsev’s 14). He’s also five years older, carries an AAV a mere $700,000 south of Zaitsev’s, and just got sold for a pair of glistening assets.

“But what about the term on Zaitsev’s deal, Mike? You idiot. You absolute moron”. I hear you, valued reader, I do. But the fact of the matter is, by the time 2024-25 finally rolls around and Zaitsev hits free agency, the soon-to-be-28-year-old will be a whole one year older than Braun was yesterday, when he managed to net the Sharks a 2019 second and 2020 third.

Getting anything for Zaitsev, let alone some mid-round draft picks, at this point would be cause for throwing a Raptors-like parade. What’s the hold-up?


Well, the market is the hold-up.

As evidenced by his t-shirt selection, Kyle Dubas prays at the altar of The Process. He’s a notoriously forward-thinking GM – not merely in terms of the progressive managerial practices he tends to operate upon, but that his decision-making process is typically one which takes into account factors that project years in advance.

Yes, the trade market is reportedly bustling with an unprecedented amount of activity at the moment, but as those assets gradually begin to fall off league-wide trade boards, Dubas’ leverage will only continue to rise.

For argument’s sake, let’s imagine that Buffalo deals Ristolainen for an overflowing, cartoon-sized chest of gold on Thursday – one day before the NHL Entry Draft. How many right-shooting defenders are left around the league?

PK Subban? He’s a phenomenal player, but the $9 million annual cap hit which accompanies him may prove too much for most teams to take on. Travis Hamonic? Another great candidate whose deal is remarkably more affordable, but the somewhat of a resurgent campaign Hamonic put forth in Calgary last season likely dictates that his services will command a stiff price. Does that then leave Colin Miller as heir to the mantle of top remaining asset? It would appear that way. And yet, Miller has seemingly been undervalued within mainstream NHL circles throughout the entirety of his career, with the fact that he fell out of favour so dramatically in Vegas possibly dampening his once-luminous shine.

Suddenly, it’s Draft Night. The floor is crowded with eager executives, each hoping to acquire the one RHD whom they believe to be their roster’s missing piece. It’s in that moment, with tensions raised and confines tight, that Nikita Zaitsev becomes the league’s most coveted available RHD.

A player whose services were once thought to require a sweetener in order to offload takes his place as the Belle of the Ball, handing Toronto a few valuable assets for a cap anchor whose on-ice performance offered them none.

Of course, every chip must fall in perfect succession for fate to trigger this outcome. The right players would have to move to the right teams and at the right time, for one. But that’s hockey for you – built on a foundation of chaos. And in light of the reported increase in league-wide activity, coupled with the sheer desperation being seen recently from a group of Dumb List™ candidates, we may very well have yet to reach the eye of the silly storm.

Such is Dubas’s dilemma. Either take advantage of the league’s currently unstable climate and risk hitting too soon, or wait until your supposed optimal moment only to watch the storm pass you by.

Come Friday, fans will likely find out which path he will choose.

Stats courtesy of HockeyReference.com

Cap information courtesy of Puckpedia.com

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  • Stan Smith

    Wow. Mike. When you started out writing about the Leafs, you showed so much promise. You wrote well thought out, intelligent articles. Now you sound just like James Tanner. If you thought it was a good idea to follow in his footsteps, you are sadly mistaken.

    I’m just going to take one piece of your article as example. You state:

    ” Cheveldayoff sent his prized asset, Jacob Trouba, to the Rangers just last night for a first-round pick HE ORIGINALLY OWNED and a 23-year-old blueliner with a career-high 5v5 CF/60 of 43.9%.”

    If you don’t understand the purpose of that deal, you do not understand today’s NHL. First of all you have a player, in Trouba, that has stated he had no intention of re-signing with the Jets. Rather than get nothing for him at the end of this season, they traded him for, #1: A 23 year old dman, who can play the PP and the PK, and who, in his first full season, scored 26 points. The only bad thing you can say about him is he had a career high Corsi of 43.9%? You make it sound like he has had a long terrible NHL career, when, in reality, he has only played one full season, and is only 23 years old. #2 He got his 20th draft pick, which, with as well as first round picks have been doing lately, is money in the bank. #3 He freed up $5.5M in cap space, on a team that has some big RFA’s to sign. To me, this was a great deal.

    I just finished reading a similar garbage article to this one, written by Tanner over in Editor in Leaf. One where, Tanner disrespected a number of GM’s in general. This article is a carbon copy of it. Please go back to writing the intelligent and respectful articles you used to write. I’m not saying agree with everything, but at the very least, show some respect.