The Maple Leafs Trade Deadline Plan


The Toronto Maple Leafs begin what is ostensibly the second half of the season tonight in Boston. Considering the kind of run the Leafs would have to go on in order to make the playoffs, the best outcome the Leafs can have in this game is an entertaining loss.

I feel like if Mike Babcock read that last sentence, he’d be pissed off. I don’t feel like he’s the kind of guy for whom a loss is ever an acceptable outcome — to say nothing of the preferred outcome. And I think the same goes for all of the players. Writers tend to analyze the team from a GM’s perspective — which is really easy, if you think about it, because we aren’t the ones who have to go out there and lose night-in and night-out.

In the end, Shawn Mattias and Tyler Bozak are not likely to be on this team when it becomes worth following again. So what do those guys care about draft picks or team building? They’re essentially fighting to stay in the league and earn contract extensions in one of the least likely ways there is to earn a living.

I forget that.

Hockey is a more than just a game you watch. All of the off-ice activities become this sort of story that never ends, developing slowly over time. You write “fire this guy,”
“this guy sucks” and “the team should tank,” but you never really think about how these are real guys with lives and fears who, for at least half of them — and I suspect more — are constantly fighting for their careers.

Sure, they are well-compensated, but that doesn’t mean they wouldn’t get pissed off if you told them to lose on purpose. I get that. But that doesn’t change the fact that, through losing, the Leafs have a chance to add the kind of franchise player that alters a team for upwards of a decade and all they have to do is lose.

Luckily, one thing that can make losing more likely but somehow less painful, is replacing veteran players with younger players. Which brings me to the one thing the Leafs actually do have to look forward to: the trade deadline.

The Maple Leafs Trade Deadline

Team Needs: Draft picks, prospects at all positions

The Leafs shouldn’t really be targeting anything specific. All draft picks are good because you can package them for higher picks, maximize the players you take or sweeten other deals. The more draft picks you have, the more options available. Other than that, the Leafs could use prospects at every position.

Untouchables: Mitch Marner, Morgan Rielly, William Nylander

While anything could happen, odds are good that these three players and this year’s (hopefully high) draft choice will make the foundation of whatever the team is building going forward.

Should-Be Untouchables: Nazem Kadri, Jake Gardiner, James Reimer

Because you can’t just build with kids, these three players represent the best of the Leafs current roster. Reimer is a perfect goalie to sign for for the next five or so years, because having him gives the Leafs a quality NHL starter they can use (that won’t be prohibitively expensive) while they develop some prospects internally.

At worst, both Kadri and Gardiner hover near the top of the second tier of players at their positions. They are both young enough to have room to grow and still be around when the team is good again. They are also good enough to keep the team competitive in the present and, when the time comes, hand the reigns to the Nylanders and Marners, while remaining excellent secondary players.

And that is a worst case scenario because ultimately, I believe that these are two amazing players any team would be lucky to have. Unless absolutely blown away with a trade offer, it makes no sense to move them.

Likely to be Traded: Mathias, Daniel Winnik, Joffrey Lupul (contract makes it doubtful, but you have to assume they’d like to move him), Brad Boyes, Peter Holland, P.A Paranteau, Nick Spalling, Matt Hunwick, Roman Polak, Marc Arcobello

These players exist on the Leafs for one reason: to be converted into draft picks. Obviously it would be a minor miracle to move all 10 players, so I think a reasonable goal is to convert five of those players into low level draft picks and consider anything above a third-rounder as a huge bonus.

Best Trade Weapon: Cap Space

The Leafs currently have almost seven million dollars in cap space, but, if I am understanding the rules correctly, which I think I am, then once they hit the cap they will then get Nathan Horton’s cap hit excepted because of his placement on the long-term injured reserve.

So while exact numbers vary, depending on where you check, it’s still safe to say that the Leafs have a lot of cap space that can be used as an asset in negotiations to acquire young players or better returns on their tradable players.

Since most teams are unable to take on a lot of salary, this gives the Leafs a great advantage when approaching the trade deadline this year.

Best Trade Chips: James van Riemsdyk, Tyler Bozak, Leo Komarov

The people who want the Leafs to keep Komarov need to be more realistic. Yes, he’s a great defensive player and yes, he’s fun to watch. However, he is also an All-Star who is massively outperforming his career goal-scoring levels.

Every team needs elite defensive players and I believe Komarov is that. But, when a player who is already extremely valuable goes on an offensive tear for a rebuilding team, that team would be silly if they didn’t sell high.

Bozak is a player who scores but doesn’t play good defense. Were I in charge, I’d be happy to leverage his recent Phil Kessel-less scoring into some kind of useful asset going forward. I believe a team can be talked into overpaying for Bozak.

As for JVR, he’s a great asset and I don’t know how you could sit on him when he is only going to decline in value going forward because he’ll get older, but more importantly, his amazing value-laden contract will have less time on it. The team that gets van Riemsdyk gets to take three playoff runs with him for only $4 million per season. It’s a great bargain and subsequently he should fetch the Leafs another top-end player to go with Nylander, Marner and Rielly.

If the Leafs keep JVR, mark my words, he’ll be their Ales Hemsky.

Thanks for reading.

RELATED: 5 Players the Leafs Must Deal at the Trade Deadline