How to cure a REALLY bad cold: A look into the crystal ball

These last few years have been nothing, but embarrassing and misleading for this Toronto Maple Leafs team. When someone is sick, they look off their game. You know who’s been off their game for years? The Toronto Maple Leafs. You guessed it, the Leafs have been sick for a while now and not in a good way. The best medicine in this case is one heavy dose of rebuild. A good rebuild is hard to find for the Leafs. Many of us thought they found it a few years ago, but turns out, it wasn’t the good stuff. It was more of the “only for temporary relief” cheap stuff. This year, the cold got worse. It consisted of symptoms such as: Dion Phaneuf, Phil Kessel, Joffrey Lupul, Tyler Bozak, etc. They went to go see Dr. Shanahan who provided them a small dose of rebuild and he promised to check up on them regularly. Dr. Shanahan then delivered some good and bad news. The good news is he can cure this really bad cold. The bad news is it’ll take as long as it will take.

Everyone has their perception of what a rebuild would have to look like for this team to get back to its winning ways. I’ve decided to make an attempt and show you what transactions I believe will benefit the organization for their rebuild. I was able to get in contact with other writers who cover different teams in the league to discuss trades that would benefit the rebuilding team and the trading partner. I put my GM cap on and went to work. To be clear, these guys have a strong knowledge of the game and the team they cover. Lastly, it is important to note that the trades listed below are trades we both agreed upon.


New York Islanders – Dan Petriw (@dandannoodles78)

TOR: Griffin Reinhart, Michael Grabner, and a 2015 2nd rounder

NYI: Dion Phaneuf

This trade involves two players in need of change; Phaneuf and Grabner. With this deal, Phaneuf will find himself on a back end in which he does not have to be relied on so heavily. The Leafs get a solid young defenseman in Reinhart whose game has progressed very well in the AHL. More importantly, Reinhart will get the opportunity to play for the big club in Toronto. Grabner’s game has dipped in the last couple of seasons, but he remains one of the league’s fastest skaters, if not the fastest. With Grabner’s contract expiring in 2016, the Leafs can flip him at the deadline for an asset or two to a team looking for scoring depth down the final stretch. The Buds will also receive a 2nd round pick in this year’s draft, something they do not currently possess.

San Jose Sharks – Tim Chiasson (@chiassontb)

TOR: 2015 1st rounder (9th Overall Pick)

SJS: Jonathan Bernier

Previously, I wrote that the Leafs should not give up on Bernier, but this is a trade I wholeheartedly endorse. This deal would give us three 1st round picks in a deep draft class. Furthermore, it would give us the possibility to package one of our core players for a stud goalie prospect or a younger goalie in the league with potential. Although Bernier is already a young goalie with potential, he wants to win and it is unlikely he will end up doing so until a few years go by here in Toronto.

Florida Panther – Alex Mieczynski (@AlexMiecz)

TOR: Jimmy Hayes, Michael Matheson, and a 2016 1st rounder

FLA: Phil Kessel

A young roster player, a prospect and a 1st rounder. I think to say you can get more for Phil is simply overvaluing him. Nylander has the potential to replace Kessel and I believe he will do so. After this trade, the Leafs will have the following right wingers: Hayes, Nylander, Panik, Grabner (from the trade above), Soshnikov, Brown, Frattin, Kozun etc. Matheson is a big and young defenseman who just finished his 3rd season at Boston College. Jimmy Hayes, also big and young, has improved a lot over the years. We’ve seen his production and overall game step up in Florida. The 1st rounder is for the 2016 NHL Draft. Given these deals, the Leafs will hold two first round picks as well as two second round picks in that draft.

St. Louis Blues – Corey Harvey

TOR: Alex Pietrangelo and Dmitrij Jaskin

STL: JVR, Jake Gardiner, Greg McKegg, and a 2015 3rd rounder

In this trade, the Leafs get a very solid defenseman in Pietrangelo as well as a good young forward in Jaskin. Some may view this as a steep price to pay, but the way I see it, we get a top pairing defensemen and a potential top 6 forward in Jaskin without giving up a first round pick or Morgan Rielly. With Rielly stepping up and Pietrangelo entering the fold, there’s no need for Gardiner in the lineup. I don’t see McKegg in our future and maybe he’ll get a chance in St. Louis. Losing the 3rd rounder doesn’t bother me since we’re acquiring another 1st and a 2nd in this year’s draft. I like JVR, but if it means getting these two players then I wouldn’t mind saying goodbye at all.

Boston Bruins – Ty Anderson (@_TyAnderson)

TOR: Reilly Smith

BOS: Joffrey Lupul

Lupul, along with his injuries, big contract and stunning good looks are headed out. I’m a fan of Lupul, but I’m tired of saying “he’s good when he plays,” because he doesn’t play often. The Leafs in return will get a young top 6 winger. Although he didn’t have a season that some hoped for, he still remains a top 6 talent that can score 20+ goals. He’s also not made of glass, so that’s pretty cool!

Columbus Blue Jackets – Brad Friedman (@BradFriedman713)

TOR: Boone Jenner

CBJ: Petter Granberg and a 2016 3rd rounder

Granberg is a guy I’m willing to part with if a guy like Jenner is coming the other way. The Leafs have a fair amount of decent defensemen in the system (thanks Burkie) and although I like how Granberg looked for us, I wouldn’t mind parting with him. I’d give up the 3rd rounder in 2016 due to the fact that we’ll have two firsts and two seconds in that draft. Boone Jenner is a big body up front (6’2” 208lbs) and can easily slide into our top 6. He can play center or wing and actually battles in the corners. His production this season (9-8-17) would have been higher than last year, if he hadn’t gotten injured. Basically, we’re getting a good hockey player.

Washington Capitals – Ben Lutz (@DCSportsDork)

TOR: Troy Brouwer and Connor Carrick

WSH: Tyler Bozak ($1M retained salary) and a 2015 5th rounder.

We get an experienced winger in Troy Brouwer who can serve as a mentor to our young guys. He plays a hard game and can put up 20 goals. Having one year left on his deal, the Leafs can also flip him at the deadline to a contending team for a couple of picks or a prospect. Carrick is an offensive minded d-man who has played a good portion of games with the Capitals and has also played very well in the AHL. Acquiring an experienced winger and a good D prospect could only be accomplished by retaining $1M of Bozak’s contract for 2 years and a 5th round pick in the 2015 draft.

It’s easy to write/tweet trades in which we think are reasonable for both sides. Trust me, it is. I considered it. Instead of writing off what I think is fair for both teams, I wanted to make it a bit more challenging. Which is why I contacted these men who were kind enough to put the time in and engage in some good trade talk.


With the Leafs most likely picking 4th overall, around 10th (San Jose trade) and anywhere in between 20th-30th, I think they should draft two of their biggest needs: A centre, a scoring winger or a defenseman. The three players I’d select in those positions, if available, would be: Dylan Strome, Timo Meier and Jeremy Roy. I don’t want to get into all seven rounds, but based on the first round, things look good already.

Free Agency

Stay away. It’s that simple. Unless, they are Daniel Winnik and Mike Santorelli type deals. I don’t think the free agent pool is deep enough to even think about signing a free agent to a multi-term deal. Instead, the Leafs should focus on spending their money towards their pending UFAs and RFAs. However, adding a cheap veteran backup (Greiss/Budaj) wouldn’t hurt. Especially, if the Bernier trade above were to happen.

The 2015-2016 Lineup

Rebuilding involves being bad for a few years. During that span, your prospects develop through the system or make the big club and mature that way. Here’s a depth chart of what I think the Leafs’ lineup will look like if the trades above actually happened:


Smith – Kadri – Hayes

Jaskin – Jenner – Nylander

Panik – Holland – Brouwer

Komarov – Bailey –Grabner

Extra: Kozun


Pietrangelo – Rielly

Erixon – Percy

Polak – Brennan

Extra: Robidas



Budaj?(Free Agent Signing)

You may feel that some of the first round picks mentioned above should be in the lineup, but I believe it’s best if they spend another season in junior. There is no need to throw them in a mess right away. They can come back when the house is a bit cleaner.

“Okay Mr. Maple Leafs, that’s all I can do for now. Let me know in eight months, if you’re feeling better or worse.”

There you have it, the Leafs took a dose of rebuild and now they must wait. I know when I’m feeling under the weather, I want to get right back up on my feet and run around, but I realize it doesn’t work like that. Take your medicine, let it kick in, and then go back to what you wanted to do beforehand. Patience is what Shanahan stressed when he took over as president and that’s what this organization and fan base need. The Leafs caught a bad cold and have been using temporary relief this whole time instead of the stuff that guarantees a full recovery. Dr. Shanahan, it’s time to search your medicine cabinet and provide us with the best rebuild you have!

Special thanks to: Dan Petriw, Tim Chiasson, Alex Mieczynski, Corey Harvey, Ty Anderson, Brad Friedman and Ben Lutz for their time to discuss the trades with me. All good guys with good work! Give them a follow on Twitter

Jordan MacKenzie (@jordanmack66)

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