The Leafs are currently fighting tooth and nail for a playoff spot, and for the most part all we can do is wait for the next game. But in the meantime: let’s talk team-building.

The Leafs should shop their first-round pick in the next three months.

Here’s why.

Stage One Of The Rebuild Is Over

Roughly, a rebuild is supposed to go like this:

Tank for core pieces Improve and add secondary pieces Contend and add complementary pieces

The Leafs are a very imperfect team, but they’re pretty clearly departing the bottom third of the league no matter how you measure it (at time of writing: 16th in points, 18th in ROW, 11th in adjusted CF%, 8th in expected goals.) It’s a transition year.

In the cases of the Chicago Blackhawks and the Los Angeles Kings, each followed a pattern of tank year, transition year, and year finishing over 100 points. The Leafs are likely going to finish with more points than either Chicago (88) or LA (79) did in their transition years. If you’re worried this is an Oilers-style false dawn, the Leafs already have more points (78) than the Oilers had any year after drafting Taylor Hall. The instinct for Leaf fans is to assume things are always about to go terribly wrong, and hey, anything can happen. But the Leafs are not tanking and should not plan on tanking in the next few years. That’s done. And the rebuilds they want to emulate did not settle in around mid-level, as you can see—after they had a transition year, they jumped to the top table.

This jump, of course, isn’t automatic. That’s the lesson of Edmonton—drafting high is not enough, even if the Leafs have built a better supporting cast than the Oilers did in their depths. The time to strike comes early, but the Leafs can’t count on internal improvements doing all the work—especially on defence. Hold that thought.

There’s a basic theory of team-building, and it goes like this: when you’re bad, trade present wins for future wins, because right now your wins aren’t doing you any good (you suck anyway, so they’re just ruining your draft position.) The most obvious example of this is teams who are “sellers” at the deadline, trading away players for picks. Be bad now to be better later.

The flipside of this is that as you improve, present wins start to become more important to you, because you’re trying to increase your team’s shot at a Cup. At the deadline, these teams are “buyers.” Be better now even if it costs you later.

Why does this mean we should shop the Leafs’ first?

What Do We Get If We Keep It?

The Leafs, right now, are sitting at the 17th overall pick (roughly.) The Leafs should know where they’re going to pick before they actually start considering a trade, but for this article let’s assume nobody more than five points below them is going to catch them and they won’t catch anybody more than five points ahead. This gives the Leafs a range of 12th to 19th for their 2017 first, assuming they don’t win a lottery.

Our starting point ought to be the draft pick value charts.

The above chart is care of friend-of-the-blog Steve Burtch. As you can see, a mid-round first is worth a hell of a lot less than a top-five pick, but is still valuable. Scott Cullen’s estimates have these picks as being more likely than not—but by no means certain—to yield an NHL player; on average, though, they tend to yield low-end talent. According to Cullen’s scale, these picks range between Fringe NHLer and a low-end NHL regular (bottom line/bottom pair.) On average, they aren’t changing the game, though some of them certainly do.

Okay. But the charts measure value ever—it’s just “did this guy eventually contribute?” The Leafs, as mentioned above, are no longer thinking eventually; they’re trying to become a contender within the next two seasons.

Between 12th and 19th, that’s eight guys a year. Of the 24 players picked in that range in the last three drafts, only three have played more than 30 NHL games yet—Jakob Chychrun, Brendan Perlini, Dylan Larkin. Chychrun and Perlini are playing primarily because the Coyotes are absolute garbage this year; Larkin is probably the ideal scenario, although I can’t help noting he’s currently tied in points for the year with Zach Hyman.

Things only start to improve once you look at the 2013 draft list. Even then, the guy picked 17th that year is running Senators punchline Curtis Lazar, and the guy picked 19th is playing for the Leafs AHL team (Kerby Rychel.) Bottom line of all this: it’s unlikely anyone we draft in this range will be contributing to our team at all before at least 2020.

Give that idea a second. Yes, I know the Bruins picked David Pastrnak 25th overall in 2014. There’s always a chance! But that’s the danger of overvaluing your draft picks. The mystery box could be anything, sure, but you have to bet on it being what it usually is—no matter how good you think Mark Hunter is at drafting. And there’s a flipside, too: as you can see above, there’s a chance whoever we pick might never play for the Leafs at all.

None of this means that a mid-round first is useless. It’s a valuable asset, and we don’t want the Leafs to fall off a cliff next decade. But it’s very easy to fall in love with some particular prospect’s game (here’s mine) and convince yourself this mid-round first is more valuable than all the other ones. This pick is a moderate chance at future wins, wins that will almost certainly not rack up until Matthews and Marner are done their ELCs. The Leafs need to strongly consider whether this pick is worth more to other teams than it is to them.

What’s The Return?

So far as I can tell, there have been thirteen trades since June 2014 that moved a first-round pick and weren’t just a trade-up/trade-down at the draft. Often the first-rounder wasn’t the only piece moving, but it was usually the most important on one side. Here are the NHLers who have come back in trades where a 1st went the other way: Kevin Shattenkirk, Martin Hanzal, Frederik Andersen, Andrew Ladd, Braydon Coburn, Phil Kessel, Martin Jones, Griffin Reinhart*, Milan Lucic, Dougie Hamilton, Robin Lehner, Keith Yandle, Cody Franson/Mike Santorelli, David Perron and Ryan Kesler.

*Griffin Reinhart is included here because this trade is hilarious.

Several of these trades were deadline rentals (Shattenkirk, Hanzal, Ladd, Yandle, Franson, Perron), while others were not. But the player sides of these deals involve a strong collection of talent, and the picks involved were usually worse than the Leafs’ pick is likely to be.

To get more specific: the hole everyone wants to patch is a first-pair RHD. I don’t know if any trade like that is possible; those guys are expensive and their teams like to hold onto them. But the highest-calibre RHD that have moved in the last couple of years are Kevin Shattenkirk, Keith Yandle, Dougie Hamilton, P.K. Subban, Cody Franson, Seth Jones, Jason Demers, Johnny Boychuk, Jeff Petry, Radko Gudas, and Adam Larsson.

Almost all of these trades involved either elite forwards (Taylor Hall for Larsson and Ryan Johansen for Jones), other top four defenders (Shea Weber for Subban, Braydon Coburn for Gudas + 1st), a grab bag of seconds (Boychuk), or first-round picks. The exceptions were Petry (2nd and 5th as a deadline rental) and Demers (for Brendan Dillon; the Sharks just got screwed on this one.) Once you accept that JVR is only going to pull so much by himself, it starts to look like our 1st-rounder is one of the best assets we can use to make this kind of deal.

Which is the other issue—the Leafs have a number of great assets they really don’t want to trade (Matthews, Nylander, Marner, Kadri, Rielly, Zaitsev, Gardiner, Andersen)...then JVR and possibly Bozak...and then a number of players of very limited value. If the Leafs want to be active in the market, they only have so many high-value resources they’d be willing to trade, and if they rule out their 1st, they simply may not be able to participate in major trades.

Ultimately, I don’t know what might come back in a deal. I do know the UFA market for RHD this summer is Kevin Shattenkirk, Cody Franson, and then almost nothing. And I know I’d like the Leafs to make an upgrade on defence. So if the Leafs feel the same way, their 1st may well be a key component in doing that.

Over To You, Lou

There’s a very big difference between “this asset should be on the table” and “we should take anything for it.” If the Leafs wind up picking with their first-rounder this summer, fine. I’d prefer no deal to a bad deal. But given the value of that asset, the Leafs should at least consider what it might bring them as soon as the draft lottery is done. There’s a potential for a bold move here.

The Leafs, as mentioned above, should be maximizing their wins in 2017-18 and especially 2018-19. Matthews and Marner will be on ELCs through that period, giving the team rare cap flexibility to acquire talent. The contention window may well stay open after that, but the Leafs should be planning to pry open that window now. That means if your 2017 1st—which is worth wins in 2021 and after—is buying you wins in the next couple of years, you want to do business.

One last thought, if you’re wondering whether Lou Lamoriello would consider this move: he dealt first-round picks—a 9th OA and a 24th OA—in deals for players twice in his last five years with New Jersey. The players? Cory Schneider and Ilya Kovalchuk.

Over to you, Lou.