What If the Leafs Took the Most Creative Approach to the Draft in NHL History?

Connor McDavid
Beset by years of bad luck, it’s not impossible the Leafs finally get a break. (Photo: OHL Images)

The Leafs are rebuilding, but people are too caught up in the idea of just being terrible for five years and drafting high. The sad fact is, historically this is not a good way to build a team – it works if you get Patrick Kane, Ovechkin or Crosby, but a cost/benefit analysis based on the odds of who you’re most likely to pick doesn’t look favorable at all.

Ironically, though his execution was flawed, Brian Burke probably had the right idea when he chose to circumvent this strategy by declaring himself not patient enough for it.  Had the Leafs thrown in the towel when they were clearly out of it, kept any of their second round picks, opted not to sign UFAs they didn’t need, and made sure to always get something back for their expiring contracts and most importantly, made better choices on who they kept and who they let leave, they would likely be a half decent team right now – perhaps even competitive.

So, while the “scorched earth” approach has been bandied about as if it’s a fact that the Leafs will do nothing but lose and draft high for the next five years, I thought it would be interesting to imagine taking an unorthodox approach to building the team.

Connor McDavid
JV who?  (Aaron Bell/OHL Images)

James Van Riemsdyk

JVR is extremely talented, he’s young and he has three more years left on a very reasonable contract ($4.5 cap hit). While he could obviously help a Leafs team in the future, his contract, age and talent level make him a very valuable trade piece.

Virtually any playoff team could afford to take him on, but I would focus on bubble teams that might want an extra push to get in, but who might also miss – important if you get their draft pick.

For JVR I would want a first rounder in the upcoming draft and a decent prospect.

(Amy Irvin / The Hockey Writers)
Rumours persist of Bernier quitting the NHL to focus on his World History degree. (Amy Irvin / The Hockey Writers)

Jon Bernier 

Everyone assumes the Leafs will keep Bernier and re-sign him in the summer. But, Bernier and Reimer are roughly the same age and have pretty similar career stats. While Bernier is considered to have more raw talent, it seems obvious to me that Reimer has more mental toughness and a willingness to battle.  Now, the key word in the sentence is “seems” because – how would I really know that?  But, if the Leafs do feel the same, I would say Reimer is the one to keep.  Especially when you consider that the difference between Bernier and Reimer going forward can probably be overcome by the fact that you could sign Reimer to a cheaper contract and get more for Bernier in a trade.

Calgary, Winnipeg, San Jose, Dallas and Philadelphia could all conceivably be interesting in improving their goaltending.

Would a fringe playoff team trade a lottery protected first rounder for a goalie upgrade to help them get in? Worth a try.

Phil Kessel

I don’t really want to trade Kessel, as he’s one of my all-time favorite Leafs, but let’s just say the Leafs could pick up a solid young player and a first rounder for him, that’s progress in the rebuild and avoids wasting his prime years to a further degree.

Let’s say the rumours come true and he goes to Florida in a package that brings back the Huberdeau and a first rounder.

Tyler Bozak

His salary and all-round terrible play means that he isn’t going to bring a lot back, but since reality isn’t exactly what we’re going for here today, let’s imagine he brings back the Leafs a second round pick – he does have points and it’s possible they could fleece someone.

(Timothy T. Ludwig-USA TODAY Sports)
Image this beauty in the Blue and White (Timothy T. Ludwig-USA TODAY Sports)

Joffrey Lupul

Despite most of his injuries being freak occurrences that happen because he is the unluckiest player in the NHL, the Leafs might have trouble moving him for a fair return on his talent.  A second rounder seems fair since, if he’s healthy, he’s a steal for the team that acquires him at that price, and the Leafs would clear salary and have a second round pick.

Daniel Winnik

I don’t know that it’s realistic, but I’ve heard pick and prospect rumours for Winnik.  Let’s split the difference and say a second rounder comes back – an incredible return on a bargain basement UFA.

Dion Phaneuf

He may have a high contact, but he’s probably worth it. He’s a great player who will look so much better when his new team gives him other high quality defensemen to play with.  Dallas clearly needs defense and I would think if the Leafs gave them lottery protection and maybe worked out a bit of a package, they could score a first rounder for his services.

The Results

The net result of these trades is that the Leafs would be hard pressed to win another game this season and would likely finish 29th, making it a decent probability that they select one of the drool-inducing top prospects available in June. Even if they lost the lottery, they’d still pick third and get a player who would go #1 in most years.

Secondly, along with their own pick and Nashville’s low first rounder, they would have four additional first round picks and three second round ones.  This is the crux of this entire exercise: picking high once per year for five years involves a ton of risk, but selling off your whole team to get that many picks in one draft isn’t really that risky since, even if you don’t get good enough players to speed up your rebuild massively – which I think you would – the worst that can happen is you pick right were you plan to for the next several years.

But this way has tons of upside – picking so often almost assures you of finding at least one diamond in the rough and all your players will get to grow together and be of an age.  (Contract time could be problematic, although not if you stagger when they start their ECLs).

Don’t forget, those six first round picks would be coming with three second round picks, Huberdeau and at least two decent prospects to add to Brenden Leipsic, William Nlander, Kadri, Gardiner, Rielly, and Reimer.  The Leafs would, at the least, instantly stock up their prospect system. Plus, if they got lucky and drafted McDavid or Eichel, we’re talking about being a powerhouse by the time a realistic timeline for a normal rebuild starts to come to fruition.

Ultimately, I know this isn’t going to happen, but it’s not that far fetched, and, even though I started the piece thinking it’d be a fun exploration on a slow news day, the more I think about it – the more I like it.  No one’s ever had 20% of an entire round of the draft before, and creativity usually pays off, in my experience.  Not to mention, the worse the Leafs make themselves before next Monday at 3PM, the better they’ll be in the future.

Thanks for reading.

8 thoughts on “What If the Leafs Took the Most Creative Approach to the Draft in NHL History?”

  1. I agree with the Field Marshall, nothing at all creative here. Turn on the two Toronto sports radio stations and you can listen to the same stuff all day long.

  2. How many other leaf fans are there that still live in the fantasy world of other teams handing over first round draft picks to take the albatross salaries of Kessel and Phaneuf off their hands? Face it – the Leafs are stuck with those two. On the entire leafs roster, only JVR, and Reilly would be worth a top pick in return. The Leafs are a bad team and will be bad for years to come until they learn how to draft and develop players.

  3. None of this is “creative” in the slightest and the entire premise makes no sense at all. The Caps, Pens and Hawks ALL TOOK THESE STEPS by dealing their higher-paid, more valuable players for draft picks. You try arguing that rebuilding in this manner isn’t assured and yet you support it by suggesting the Leafs should do it…? HUH??

    How is what you wrote and propose any different from what the GMs of the Caps, Pens and Blackhawks…?? You totally ignore realism in that teams aren’t going to simply hand out first-round picks at will just because the Leafs want them to.

    You REALLY need to get a grip about the Leafs and find some consistency with your writing (and also actually take some time to proofread, or have someone edit for you). Two weeks ago you wrote a piece about how the Leafs’ rebuild “wouldn’t take very long”, noting some prospects you believed were valuable (FAR more valuable than anyone else sees them), and then the week after you tore down the same guys you were touting.

    I don’t think anyone can seriously read your material expecting much credibility if the writer constantly flip-flops and is entirely unable to grasp realism regarding the direction of the team he writes about and uses obscure stats and extreme personal bias to “prove” his thesis.

  4. Two things make a hockey team that can stay at the top in this league – drafting correctly and developing talent. Trying to trade these guys for picks is the right approach. Issue being that Toronto hasn’t really drafted and developed well. They have to get that part of their organization right, or draft picks mean nothing. How many first round picks are the Wings playing? Sheahan and Kindl and Kronwall. The rest are lower draft picks that developed, or free agents.

    Extra draft picks would help as well, because even a blind squirrel finds a nut. I just think expecting first round picks to save your organization is indeed a scary prospect as you somewhat touch on – for every Chicago and Pittsburgh, there are probably 10 Edmontons and Calgarys that never get traction.

    I guess the point is that I would go for as many guys as I could, and would rather try to trade for say both a second and a third rounder rather than one first rounder. More chances to “get it right.” No, I’m not a Leafs fan but I respect your team and tradition and fans. If I were in your position, I would want the Leafs to get as many picks as possible and get their development and draft picking to be more effective.

    And maybe a head coach that doesn’t suck would be good, too.

  5. I opened this article expecting to read another ridiculous post by a blinkered Leafs fan who doesn’t have a clue about his players’ true worth. Actually each one of these proposals seems eminently reasonable. Nice job!

  6. Take a look at Edmonton… How are they doing now with all the first picks… You need cohesiveness between players.. You don’t need all to be young…

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