Maple Leafs Trade Deadline 2016: Justin’s Three Dream Trades

Hi, TLNers. I’m on vacation in Barbados this week. As such, I am drinking a lot of rum punch and thinking about hockey. Rum punch is a lot of rum in a lot of orange and mango and pineapple juice with a lot of mint leaves in it, all stirred up and served over ice. Here are three hockey trades I’ve come up with that I think are relatively reasonable that the Leafs should try and get done by next Monday’s trade deadline. If you think I’m crazy, like… I just finished telling you about the rum punch. 

I am drunk.

It just makes too much sense to me.

James van Riemsdyk is a good player. He’s a great player, in fact. But as they say, you have to give something to get something, and I want to get one of those young, amazing defencemen that the Ducks have. 

I know I probably sound like a broken record, but the biggest organizational weakness is the blueline. Ok, maybe it’s goaltending – but any team can go out and usually find league-average goaltending fairly easily and get by. On defence, though, Toronto has Morgan Rielly and Jake Gardiner and a bunch of other guys who may or may not be everyday NHLers. They could really use another top-four guy, but as of right now there isn’t one in the system. You hope that Travis Dermott or Andrew Nielsen or Rinat Valiev have it in them, but there’s no blue chipper back there, and that’s concerning. 

As good as JVR would look playing alongside William Nylander or Mitch Marner in the coming seasons, Toronto looks to have a number of offensive weapons on the way and van Riemsdyk’s value will never be higher. He’s got an incredible contract, but pretty soon he’ll become either a rental player or a pending free agent. If you keep him much longer, his trade value drops or you have to hand him a big contract. Well, that, or lose him for nothing. That’d be a nightmare.

So why not call up the Ducks and talk about those D? I start off by sniffing around Hampus Lindholm, the 22-year old lefty that Anaheim selected with the sixth-overall pick in the 2012 draft. He’d be the top target for any team looking to pick up one of Anaheim’s blueliners. Something tells me, though, that Lindholm is a no-go from the Ducks’ perspective, and it’s more likely they’ll look to deal 24-year old Sami Vatanen instead. Vatanen, who leads Anaheim with 30 points in 58 games this year, would be an excellent consolation prize. The fact that he’s a right-handed shot and looks every bit like a top-pairing guy is a huge bonus. 

I suppose that if it turned out Anaheim was unwilling to move either Vatanen or Lindholm, there’s still some more options to explore. For example, if Anaheim was more interested in dealing futures (and Toronto was looking to get as young as possible), then a package surrounding Shea Theodore could also be considered. Theodore, 20, was the Ducks’ first-round pick in 2013 and made his NHL debut this season with six points in 13 games played. Pair him with a draft pick or another prospect and you may be well on your way to building a van Riemsdyk-worth package.

Still, I’m on that Sami Vatanen bandwagon. I think that a JVR-for-Vatanen deal makes a great deal of sense for both teams, though, a lot of smart hockey folk that I talk to think that Anaheim should be the ones to sweeten the pot a bit in this kind of situation.

I’m not sure exactly what it is, but I can see Komarov excelling in a secondary role in Washington. Maybe I’m just putting too much stock into the fact that Nick Backstrom and Alex Ovechkin played with Komarov in Moscow and there’s a familiarity there, but I do think that Uncle Leo would look great playing alongside either Backstrom on the second line or Mike Richards on the third line. It just seems like a wonderful fit to me.

But of course, I’m not really looking out for Washington’s best interests here, either. While I personally don’t believe Komarov is the ideal top-six forward, he does lead the Leafs in scoring and was an NHL All-Star, so I guess that’s gotta be worth something, right?

Right. So my second dream trade would be Leo Komarov for Washington’s Ilya Samsonov. I honestly don’t know what the Capitals were trying to accomplish exactly when they selected the 6’3 goaltender in the first round of the 2015 Draft, but if they did it so that they may trade him to Toronto later, I guess that makes sense. Samsonov, 19, sports an impressive .925 SV% and 2.04 GAA in 19 games for Magnitogorsk in the KHL this season. We all know that goalies are, of course, voodoo… but those are excellent numbers, and Samsanov is considered one of the best goaltending prospects in the game today. 

With Braden Holtby locked up for four more seasons, doesn’t it make a lot of sense for Washington to use their goaltending depth and stock up for a deep playoff run? I think so, and maybe Komarov isn’t the guy they want to use that bullet on, but I certainly hope it is. Samsonov would obviously become Toronto’s newest goaltender of the future, and could backstop the team for a very, very long time. If you don’t want to spend high draft picks on top goaltending prospects, trading Leo Komarov for one isn’t a half-bad alternative.

If Washington can’t stomach moving Samsonov, though, I’d also accept a Madison Bowey return as well. I mean, I’m not an unreasonable guy. Another 2013 pick like Theodore above, Bowey was drafted in the 2nd round by the Capitals out of Kelowna and made his pro hockey debut this year with AHL Hershey. He currently has 19 points in 49 games for the Bears and is also a right-handed shot. That’s always nice, and something Toronto could desperately use. 

I really like Chicago as a trade partner for Toronto, because Toronto has a ton of cap space and Chicago desperately needs some cap relief. As such, I think there’s a good opportunity for the Leafs to leverage their enviable financial situation and pry a nice asset out of the Blackhawks.

To get a great asset, though, Toronto will need to help Chicago in the present and in the future. I think they can accomplish that with P.A. Parenteau. In exchange, the Leafs get a 2016 first round draft pick and buried winger Bryan Bickell.

Bickell is what makes this deal work, to be honest. He carries a cap hit of $4M per season and is on the books for one more year after this. Chicago currently has him buried in the AHL, which they’d say is providing them some relief, but really they’re being penalized to the tune of $3.05M. With Parenteau only making $1.5M until the end of the season, that opens up $2.5M for Chicago this season and a full $4M next. That kind of relief shouldn’t come cheap, though, and that’s why they’ll cough up a shiny first rounder to get it done.

And maybe, just maybe, Bickell becomes an asset himself. The guy was beastly in the playoffs a few seasons ago, earning him that massive paycheck he now enjoys. Is it possible that under Mike Babcock’s tutelage, Bickell could find his game again and become a deadline target for other teams next season? I think so, and especially if Toronto agrees to eat a significant portion of that contract for a few months until he comes off the books completely. If all worked out, that $1.5M investment in Parenteau could turn into a first-round pick and, say, another third-round pick. That’d be a sweet, sweet haul.

Previous Deadline Week Posts:  

Maple Leafs Trade Deadline 2016 Primer (Jon Steitzer)  

Maple Leafs Trade Deadline 2016 Inventory (Ryan Fancey)