With the potential that the 2020 NHL Draft may be coming sooner rather than later, it’s time to get fully on board with the draft hype, as we may finally have some kind of hockey content that doesn’t involve re-watching old hockey games.

One of my favourite parts about drafts is looking back on them several years later, and seeing how good or bad some teams did every year, as well as some of the busts in the early rounds and hidden gems found in later rounds.

So, I’m going to do just that with Draft Flashbacks. This series will take a look at each individual draft and re-examine every pick the Leafs made, and see who was the best pick available with the hindsight of seeing what kind of player they’ve turned into. And to finish it off, I’ll do a what if scenario based on the best possible drafts the Leafs could’ve had.

Today, it’s the 2014 draft, which the Leafs did surprisingly well in considering that this was still in the Dave Nonis era (only Shanahan was in the organization at this point) and the Leafs only had six draft picks (you can thank Ryan O’Byrne, Roman Polak, and Dave Bolland for that one).


Round 1: 8th overall

Who the Leafs picked: William Nylander

Best player available (within 20 picks): David Pastrnak (Boston, 25th overall)

Best player available (overall): David Pastrnak

It pains me to type these words, but the Leafs probably shouldn’t have drafted William Nylander in 2014. I say probably because aside from Pastrnak and Brayden Point, he was arguably the best player available (with some debate for Dylan Larkin, Nikolaj Ehlers, and Aaron Ekblad), so taking the fourth best player in the draft at 8th is still really good.

But, Pastrnak was not only the best player, he’s arguably the best player from this draft class, depending on how you feel about Leon Draisaitl. Those two are the only players with more than 300 points up to this point, and with Draisaitl already taken at third overall, it makes an easy pick for David Pastrnak at this pick.

Mar 10, 2020; Toronto, Ontario, CAN; Toronto Maple Leafs forward Kasperi Kapanen (24) and Tampa Bay Lightning forward Brayden Point (21) battle for the puck during the second period at Scotiabank Arena. Mandatory Credit: John E. Sokolowski-USA TODAY Sports

Round 3: 68th overall

Who the Leafs picked: Rinat Valiev

Best player available (within 20 picks): Brayden Point (Tampa Bay, 79th overall)

Best player available (overall): Brayden Point

As far as third round picks go, Valiev wasn’t half bad, managing to get into 10 games with the Leafs (albeit with the 2015-16 tank team), and eventually helped as an asset in the Tomas Plekanec trade. Not amazing, but far from a bad pick. That said, he’s no Point, who has developed into an elite player for the Tampa (probably even better than Stamkos at this point), and has 260 points in 294 games. That somehow gives us better centre depth than the 2015 re-draft.


Round 4: 103rd overall

Who the Leafs picked: J. J. Piccinich

Best player available (within 20 picks): Viktor Arvidsson (Nashville, 112th overall)

Best player available (overall): Viktor Arvidsson

Piccinich didn’t really amount to much as a fourth rounder, as he’s only played 10 games in the AHL between the Marlies and the San Antonio Rampage. He’s a solid ECHL player, but not exactly what you draft a player to become. This rounds edition of hidden gems is Arvidsson, who has been a key part to the Predators recent success, and has been a strong offensive contributor, although his 2019-20 campaign hasn’t been as strong.


Round 5: 128th overall

Who the Leafs picked: Dakota Joshua

Best player available (within 20 picks): Oskar Lindblom (Philadelphia, 138th overall)

Best player available (overall): Ondrej Kase (Anaheim, 205th overall)

I kept thinking that Dakota Joshua had played some games with the Leafs, but then I realized I was thinking of Casey Bailey (remember him?). Anyways, Joshua has apparently taken the Piccinich route of now going between the Rampage and the Tulsa Oilers, so there’s another pick that didn’t work out well. It wasn’t exactly an amazing round for most teams though, as the best player to come out of it was Lindblom, who has rounded out as a bottom six forward with some potential for a bit more (that said, best wishes to Oskar as he continues his battle with cancer).


Round 6: 158th overall

Who the Leafs picked: Nolan Vesey

Best player available (within 20 picks): Kevin Labanc (San Jose, 171st overall)

Best player available (overall): Ondrej Kase

Oh wow, speaking of bad rounds of the draft, this one takes the case. There’s actually a case for Nolan Vesey being the fourth or fifth most significant player drafted in this round, mostly because he was a supposed chip to help the Leafs sign Jimmy Vesey (who has turned out great, by the way, glad people thought we should trade Nylander to make room for him). That’s not to say that there were no good players drafted, as Kevin Labanc has turned into a good forward for the Sharks, even if he’s had an iffy 2019-20 campaign.

Nov 21, 2019; Glendale, AZ, USA; Toronto Maple Leafs left wing Pierre Engvall (47) celebrates his goal against the Arizona Coyotes during the second period at Gila River Arena. Mandatory Credit: Joe Camporeale-USA TODAY Sports

Round 7: 188th overall

Who the Leafs picked: Pierre Engvall

Best player available (within 20 picks): Ondrej Kase

Best player available (overall): Ondrej Kase

And after a few iffy rounds, we encounter a hidden gem of our own. Engvall took a while to make his round, only just making it to the Marlies for their Calder Cup run, but he’s developed into an excellent bottom six forward with some potential to be a third line center for us down the road. That said, he wasn’t the best hidden gem in this round, as Kase was selected with just the sixth last pick of the draft. In a perfect world, we draft him, but for a seventh rounder drafted in the Nonis era, I will take Engvall any day.


What If?

Ideal Draft

8th – David Pastrnak

68th – Brayden Point

103rd – Viktor Arvidsson

128th – Oskar Lindblom

158th – Kevin Labanc

188th – Ondrej Kase

As far as the impact on the roster goes, it means bye-bye Nylander and bye-bye Engvall, as well as the conditional seventh we got for Vesey (which they didn’t get anyways).

But you could probably dive deeper as well. If we have Pastrnak on his current deal like the Leafs wanted with Nylander, does that mean that Dubas becomes a better negotiator (if it’s even him that signs it), and does that in turn mean Matthews and Marner take cheaper deals? Or if Lou is the one signing the deal, is it handled as well and does he end up signing him to a higher cap hit and cause Matthews’ and Marner’s deals to be even higher?

And while we’re at it, imagine Pastrnak on this year’s team. Does he and Matthews both put up 48 and 47 goals, or does that get spread out more? Heck, imagine them putting up those totals on the same line! So many unnecessary, but fun, hypothetical questions!

Using Charting Hockey’s WAR Lineup Creator, this would be the ideal lineup with these new draft picks. It pretty much only affects our forward group, as our defense and goaltending remain the same. It does completely overload our right wing side, as Labanc doesn’t even crack the current roster, and like every other time we’ve done this, makes a lot of wingers expendable.

That center depth though.

Overall Evaluation

While Nylander wasn’t the best pick available at the eighth spot, he still probably should’ve been drafted ahead of his position, so that’s still a great pick for the Leafs (despite what some people may try to tell you). We also got Engvall out of this draft, and Valiev at least provided enough value for us to deal him. No one was the best player available, but they could’ve picked a lot worse in those positions, not to mention that the later rounds had almost nothing of substance in terms of players with NHL experience.

Overall, getting three players of substance in a draft where we only had six picks is excellent work (now, why we had only six picks is a different story), and it should be looked back was one of the Leafs better ones.

Grade: B

Quick note: To make the grading a little bit more consistent, I’ve done away with +’s and -‘s, and will strictly go with letter grades from this point onward. I’ve also applied this to the previous two articles and adjusted those grades as such.