As the expansion draft process draws to a close tomorrow and things open back up heading into this weekend’s prospect draft, the trade rumour mill will start to turn again, likely even more than it did last week.

The entry draft has often been where big deals are cut, or at least where they originate. In recent years we’ve seen trades involving Phil Kessel, Taylor Hall, and PK Subban all have the seeds planted on draft weekend and evolve from there. This summer should be no different.

We’re already seeing some of this come about, and a piece of speculation that caught my eye yesterday was this Larry Brooks piece on how the Rangers have apparently made Derek Stepan available, and how that could spin into a trade of major substance. Looking through the Leafs’ lens, obviously Stepan isn’t a player they would be interested in, but it’s the potential targets that Brooks outlined that are intriguing.

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Derek Stepan has considerable value on the trade market, but unless the Rangers are able to parlay moving him into a no-doubt, first-pair right defenseman, Stepan’s greatest value is on the ice wearing a Blueshirt in 2017-18. It does not appear the Blueshirts currently have the piece(s) to land Winnipeg’s high-end Jacob Trouba. But, for instance, if the Coyotes are willing to deal one of their stable of highly regarded young forwards that includes Clayton Keller, Dylan Strome, Christian Dvorak and Max Domi in a deal for Stepan, the Rangers could then flip that piece to the Jets for Trouba. If Carolina is willing to talk Justin Faulk, then by all means…

Two huge names there: Trouba and Faulk. But right now let’s focus on the former.

Trouba is a player that’s been in the news in recent years the same way Jonathan Drouin has. Both demanded trades from their teams, then rescinded them and signed two-year bridge deals as restricted free agents. Drouin’s bridge just ended, and the Lightning decided to ship him out instead of paying him. Trouba’s will end in 2018, and putting aside the potential that his desire to leave Winnipeg could still be there, the financials of this on their own could pose some problems for the Jets – a team with an internal budget.

The Winnipeg Jets are nearing the point where very good young players will need new contracts and will become much more highly paid than they already are. A player like Jacob Trouba will surely command more money than Dustin Byfuglien’s $7.6 million/year contract. Josh Morrissey will be coming off of his entry-level contract at the same time. Morrissey’s excellent rookie season means he should be projected for a raise as well, but probably more in line with Trouba’s current $2.8 million cap hit. This does not even include the forwards where Nikolaj Ehlers and Patrik Laine are going to need new contracts over the next two seasons. What should the Jets do?

(Hand up) I have an idea. Trade him to Toronto.

Like Brooks pointed out above, there’s no chance Stepan, at 6.5-million AAV, is a player that moves the needle enough for the Jets to part with Trouba. They’ll likely only take on manageable contracts, long-term futures, and those that are on the cusp. The Leafs have all of that.

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James van Riemsdyk is a name that sort of makes sense here, because, for one, he’s a far better offensive player than Stepan, and has a year left on a cap-friendly contract. Of course he’s going to look for a raise next summer, but at least the Jets control their own price point there. If they don’t feel it’s going to work out, they can flip him again at the deadline for more assets. [Keep in mind JVR does have a limited no-trade list 10 teams, but we have no idea what that looks like.]

But JVR alone isn’t going to get a deal like this done. If anything, he’s almost the throw-in. Toronto would need to go further, much further, to put together a package that essentially solidifies their back-end for the next decade. How far?

A first-round pick and JVR is a no-brainer, then we need to start cutting into the prospect pool for players who can help the Jets, but not too far down the road. Think Dermott or Grundstrom. Actually, think both.

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This is probably the point in this article where readers begin to think “This is too much to give up”, but Trouba really is that good. In fact he’d step in as Toronto’s best overall defenceman right off the hop, and at 23-years-old no less. His ceiling is right there to be hit over the next 3-5 seasons.

So let’s do some spit-balling. Is Toronto in the position to give up something like this, below?

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To WPG: James van Riemsdyk, 2017 (or 18) first round pick, Travis Dermott, Carl Grundstrom

To TOR: Jacob Trouba, Mark Stuart (salary dump expiring in 2018)

Admittedly, when I floated this to some of my colleagues here, we got to a bit of an impasse. Am I vastly overrating Trouba and overpaying for him? A couple writers believed so. But here’s some further explanation behind why I think it’ll take this much. [There’s part of me that thinks even this isn’t enough.]

First off, as great of a player as James van Riemsdyk is – inarguably a top six wing – if the Leafs are resigning themselves to trading him, his actual value on the market isn’t all that high. As it’s been pointed out here before, he’s most valuable in a Leafs sweater. Should they move on from him, a team looking to bring him aboard is doing so knowing full-well he could be looking forward to free agency next summer. He’s a solid trade chip because he helps any team right now in a big way, but let’s not be those fans who overvalue our own too much.

The first round pick goes without saying. It’s 17th this year, likely even lower if it could be a 2018 selection. It’s a magic bean.

The hangup is in the young pieces required to make something like this work. Grundstrom and Dermott appear to be on track to become NHL players, but I think any deal with a return of Trouba’s magnitude is going to require two players from this second tier (the first tier of course being The Big Three of Marner, Matthews, and Will Nye.) I just don’t see how the standard “Roster player, plus a pick and prospect” package is enough to move the needle on acquiring a 23-year-old cost-controlled number one defenceman.

Either way, none of this is rooted in real speculation between Toronto and Winnipeg. But if Trouba’s name is indeed out there, Toronto should blow the doors off to make it happen if they can do so without cutting into that aforementioned top trio.



