Hey, you!

Me?

Yes, you. You’ve been speculating about trades, haven’t you?

Oh, not really.

Be honest.

Maybe a little bit.

And they’ve been really bad.

Hey!

We need to address this. We’re all worried about you. “JVR for Drew Doughty”? “Josh Leivo and Nikita Soshnikov for Oliver Ekman-Larsson”? “Connor Brown and a second for Dougie Hamilton”?

Those work for both teams!

Do you really believe that? Deep down?

....yeah...

Be honest.

....maybe they’re a little uneven.

They’re a lot uneven. They’re a seesaw where one end is covered in fat children. But don’t worry. Lots of people make bad trade proposals. Today we’re going to help you fix that.

Step 1: There Has To Be A Good Reason For A Good Player To Move

This is a very important first step. The Kings are not going to trade Drew Doughty for shits and giggles. The scenario where they trade him during this season is basically that he goes on television, does the Ron Burgundy thing, and tells the entire city of Los Angeles to eat shit. He’s a top-five defenceman in the NHL on a team that is doing reasonably well and is contractually blocked from attempting a rebuild in the next two years. His deal does not expire until summer 2019. Forget about him for at least the next seven months.

But what if we made an offer that was so good they couldn’t turn it down?

Sure. Give them Mitch Marner and Morgan Rielly, they’ll do that right away.

That’s crazy! I was thinking more—

STOP. STOP RIGHT THERE.

You only get elite players:

a) in exchange for other elite players

b) in exchange for a big rebuild return, if the team is doing a tear-down

c) as expensive rentals

d) because the other GM is Peter Chiarelli

All of the deals that would get you Drew Doughty, or for that matter, Hampus Lindholm, or Jacob Slavin, or Dougie Hamilton, or whoever are going to involve a price you are not going to be willing to pay. Okay? Imagine a trade that would make you angry at the mere suggestion of it. That’s what it would cost.

Step 2: Loot Bags Are For Birthday Parties, Not Trades

Okay, so you’ve adjusted your aims a little bit. You’re still looking for a right-hand defenceman for the Leafs, but you’re looking at candidates who might be a little more attainable. How about Chris Tanev, from the Canucks? He’s good, but he’s not so unattainable he’d cost the farm, and his team looks to be starting a rebuild. That seems like a good fit!

What if we gave them Josh Leivo? And Martins Dzierkals. And a third.

This is the sort of thing you see all the time, and it is deeply annoying. Because, if we’re being honest here, the average fan does not care about Josh Leivo, Martins Dzierkals, or a third, because those assets are respectively a fringe forward, a faint-hope prospect, and a pick that no one cares about because no one actually has any interest in picks after the second round. In exchange, we get a borderline top-pair right hand defenceman who is under contract for three years. Dope trade!

The idea of this is sometimes called three dimes for a loonie. I call it a loot bag. Imagine you are nine years old, at the birthday party of a kid you are reasonably friendly with but not like, friends friends with, you know? He got a bunch of cool presents because you are in an affluent community for this hypothetical. At the end of the party, his mom hands you a loot bag with three gumballs, those little Rocket candies that taste like sugary chalk, and some gum. Now go to your reasonably friendly friend and offer him that loot bag in exchange for his new Nintendo Switch.

Pretty much every time someone tries to defend one of these trades, they’re just telling you how tasty the gumballs are.

Well, we gave up Phil Kessel for a bunch of lesser assets.

Yep! And that was clearing a huge amount of salary, it got us our current best forward prospect in the system, it got us a first-round pick, and it was still an uneven trade forced by our management’s desire to clean house. At the very least, if you’re trying to get a real difference-maker, you have to give up a meaningful pick and a meaningful prospect. That doesn’t mean a 24-year-old who’s pitched a tent in the press box, no matter how nice his P/60 looked last year.

Step 3: Your Trash Is Not Someone Else’s Treasure

One odd thing about hockey fans is that sometimes they develop split personalities. About the same player. At the same time. Hey, fictional reader I’ve created for the purposes of this piece, what do you think of Jake Gardiner?

Turnover machine. He’s been getting killed this year, he’s not even putting up the shot numbers he used to.

Should we look at trading him?

Definitely.

Why would anyone want him?

Well, he’s a clear top four, he’s a good skater, he produces points, he normally does have good shot nu—

Why don’t we keep him?

...he makes me angry sometimes.

This isn’t so much a direct barrier to a trade—maybe you could construct a logical trade around Jake Gardiner, although this is probably not a team that should be dealing out top-four defencemen—as a really bizarre thought process that people go into. This guy is crap, so we have to trade him, but people will trade a lot for him, because...I guess they’re much dumber than us?

In the odd case this might actually be true, but the vast majority of the time, it’s a sign that people have a really strange valuation issue going on in their own heads. You see this in particular with (in addition to Gardiner) James van Riemsdyk. Last week I saw a Reddit thread where someone rained on both players for being garbage and then, and I swear to God I am not making this up, proposed packaging them both with a second. For, you guessed it, Drew Doughty.

If you’re trying to make a trade, you have to come to a clear idea of the values of the players in the trade, and then—sorry—you probably have to assume the other side of the deal is going to have at least a semi-realistic conception of that value. There are rare, spectacular examples where GMs make very skewed value judgments—Taylor Hall for Adam Larsson—but for the most part, you aren’t going to get a player who is clearly established as good for players who are clearly established as not good. Sometimes you can win a trade handily based on acquiring prospects and potential, but people oddly don’t seem to fantasize about trading for guys who are developing nicely in the AHL that much. Arguably the most lopsided trade of the last decade was Filip Forsberg for Martin Erat, but it was possible partly because Forsberg had yet to play an NHL game.

All I got out of that was that we can trade JVR.

Sigh. Next.

Step 4: Maybe The Fit Just Isn’t There

For the past year or so, the most popular trade candidate on the Leafs has been James van Riemsdyk. This is not crazy, in itself. JVR is a very talented scoring winger, but the Leafs have a deep forward lineup already, and they may not be able to extend him beyond this season. We would definitely miss him if he went, but maybe the right choice is to trade him.

The thing is, what teams are going to want to acquire James van Riemsdyk? Barring a trade packaged with an immediate extension (which is rare in hockey; Kyle Turris is the most prominent recent example), JVR is going to be a rental. Teams that are going to want to acquire him are trying to contend this season.

This already starts to get a bit odd, since the Leafs are also probably trying to contend this season. The assets you get from a team that wants to contend now tend to be futures and picks. Those are nice, but if they mean the Leafs get worse in the short term—and they will—it’s questionable why the Leafs would do it. Maybe if you’re convinced you have a solid-gold prospect in the AHL...but if the guy were NHL-ready, he’d likely be playing for his club.

So maybe we could trade him for a defence rental?

In theory. What you need, though, is a team that’s really strong on defence, enough that they want to make a run this season, but that needs more scoring. The teams that might fit that category, as far as I can tell, are Calgary, St. Louis, Anaheim, and Nashville. None of those teams have a top four defenceman who is about to expire UFA.

So...as much as we might want to do something, maybe the reality is there just isn’t a fit out there. Sometimes inaction is better than forcing a bad deal, boring as that is.

You’re really taking all the fun out of speculation.

I know. Which brings us to our final point.

Step 5: If It’s Fair And It’s Meaningful, You’re Gonna Have To Give Something Up

The real problem here is that any trade that feels comfortable for a fan of one team is probably light on one end, and that’s no good. I wrote a piece speculating on the cost for Chris Tanev last summer (I guessed that the high offer should be Kapanen + Brown + 1st, fwiw.) You can think my deal was good or bad or whatever, but the interesting part was it got posted both on the Leafs and Canucks subreddits. The Leafs fans thought I was crazy for giving up Kapanen. The Canucks fans were insulted that the offer didn’t start with William Nylander.

The reason HF Boards is such a gold mine of terrible trade ideas is that fair trades don’t tend to end with one fanbase feeling glorious and vindicated in their excellence, but that’s all anyone wants to feel. You’re not going to get something for nothing. And if you have an elite player coming your way in exchange for mediocrity, you’re either kidding yourself....or you’re talking to Chiarelli.

We should talk to him!

Leivo + Dzierkals + 3rd for Klefbom. Helps both teams, imo.