Trading Up and Down: A Recent History

I’m not going to sit here and give you a lecture on whether trading up or down, historically, is a good or bad idea. That’s mostly because Shawn Reis did a fantastic job of that back in May, and quite frankly, I have nothing more to bring to the table beyond what he’s said.

However, I do have a handy list of times the Leafs have actually made a pure draft pick shuffle in the past few years, so let’s take a look at a few case studies, shall we?

The Fall of 2015 (Trade Down)

June 26th, 2015:

  • Toronto trades 24th overall to Philadelphia for 29th overall, 61st overall
  • Toronto trades 29th overall to Columbus for 34th overall, 68th overall

Analysis: It’s very early to tell here, but Toronto seems to have picked up a pretty likable haul here. While their original pick was used to select Travis Konecny, a faller who had very good Draft+1 numbers until suffering a shoulder injury this year, the Leafs managed to pick up Travis Dermott, Jeremy Bracco, and Martins Dzierkals in return. All three seem to be progressing to expectation, if not ahead of it.

Would I Do It Again? Probably. It’s early, but Toronto managed to secure three very solid prospects thanks to this move, taking advantage of what looked like a foregone conclusion that Bracco would fall to them if they could time their scoop up.

The Anaheim Swindle (Trade Up)

June 24th/25th, 2011:

  • Toronto trades 30th overall and 39th overall to Anaheim for 22nd overall
  • Toronto trades 160th overall in 2011 to Anaheim for 157th overall in 2012

Analysis: Man, did Brian Burke’s former team get the best of him on this one. The Leafs wanted a bruiser forward up front and thought they were going to get one in Tyler Biggs, so they took the leap of faith. Biggs was a disaster in Toronto and hasn’t been much better in Pittsburgh’s system. The Ducks picked up Rickard Rakell and John Gibson, who have become meaningful young roster players.

Toronto also pushed a pick back a year thanks to a shuffle in a year prior (more on that in a minute) and ended up effectively trading Josh Manson for Ryan Rupert. Manson will play his 100th NHL game next year; Rupert looks to be a decent-ish AHL player.

Would I Do It Again? hahahahahahahaha *cries self to sleep*

What Year Is This? (Both)

June 26th, 2010:

  • Toronto trades 66nd overall in 2012 to Los Angeles for 79th overall in 2010
  • Toronto trades 202nd overall in 2010 to Edmonton for 152nd overall in 2011

Analysis: As hinted at before, this was peak Burkey, looking to get what he wanted in the present while worrying about the future as he went. He felt that he had spotted a gem in Sondre Olden and traded a 3rd round pick two years in the future to draft him; Olden never panned out and that pick became Jimmy Vesey.

To make up for it, the Leafs got rid of one of their sixth round picks in exchange for a 5th rounder in the following year. That’s a powerplay, and while David Broll didn’t end up being much either, he’s seen more meaningful action than Kellen Jones.

Would I Do It Again? Probably not, but if we find out that Vesey was going to test the market no matter who he was with, then sure. The biggest issue here was that Burke thought the Leafs in 2012 would be a good team, and ended up trading down 13 spots on the first move. If you’re self-aware of your long-term outlook, though, shifting years makes sense. Ideally, however, you’d like to get another pick thrown in so you’re amassing swings in the process.

The Eraser Chaser

June 20th, 2008:

  • Toronto trades 7th overall, 68th overall, and 37th overall in 2009 for 5th overall

Analysis: That’s a very, very steep price to pay for two spots, but the Leafs were certain that they had found the NHL-ready prospect who was going to kickstart their rebuild. The good news was that he made it to the NHL right away; the bad news is that it was Luke Schenn. Toronto’s picks ended up becoming Colin Wilson, Shawn Lalonde, and Mat Clark.

Would I Do It Again? I probably wouldn’t apply those pick numbers to a current draft trade, but this specific one? Hindsight works in funny ways. Schenn wasn’t overly great, but Wilson, while good, is far from a star. There isn’t really anybody mindblowing directly below him either, unless you think the Leafs would have gone off the board for Karlsson or Myers at 7. Not a lot was available around Lalonde and Clark’s spots either, which softens the blow. Besides, they managed to get James van Riemsdyk for Schenn a few years later, and that’s still hilarious.

  • DSP

    Draft is always a gamble. Remember when Alexande Daige (Spelling) was going to be what you guys think Mathews is going to do. All I’m saying is it’s always a gamble when you make that choice. Hindsight is always 20-20.

    • Newleafs

      Except that Matthews has already put up numbers not far off NHL stars (during the lockout) in a professional league. And in the Worlds he was impressive against even stronger competition. He broke the record for scoring for 18 AND 19 year old players in the NLA. Matthews is as sure a thing as you can get. He’s already proven he can play with men and against elite talent. Most players we have to wait and find out if they can play well against men/professionals. Matthews can more than play: he was 2nd in MVP voting at the age of 18.

      Comparing him to former busts I think we can see there is already strong evidence of how well Matthews will do. Because he’s already done it.

    • Jeremy Ian

      Hindsight is never 20:20 (whatever that means); there’s always a bias — in fact, it’s called “hindsight bias.” It means claiming a determination when there’s little objective evidence for it.

      Hindsight bias can lead to as many bad judgements as the fallacies of foresight. It leads to terrible court decisions, bad medical diagnoses, and awful history (I am a historian, so it’s something I carp on all the time to my students).

      Since we are Leaf fans, we should be wary of hindsight bias. For instance, one casualty is that we should have known all along that Schenn was going to be a disappointment, and we are going to beat Burke up for the rest of his life for it.

      We can beat Burke up for many things — but maybe not for that one. Schenn may have been a victim of bad coaching and preparing. It may mean that the choice to trade up for Schenn was not a bad one as much as the choice to throw him on the ice as a teenager under Ron Wilson.

      I say this because we can draw the wrong lessons from this anecdotal evidence. The way Jeff — sorry to pick on you here — has narrated the story, trading up has tended to look worse than trading down. So, only a fool would follow the trade-up strategy.

      Don’t let the “it’s all a gamble” line mean that we should prefer to trade down and sweep up as many picks as possible because they are all “a gamble.”

      If the data point to a gem that you can get by trading up, then a trade should be in play.

      Lesson here is: our scouting has to be really good, and the commitment to a long term strategy.

      This is a key draft year to test Shanny et al. Should be great to watch.

    • Bob Canuck

      If you look at the 1st overall picks in the 90s, there are a lot of “wouldn’t have picked that guy” choices. After diPietro in 2000, I think it’s fair to say that the worst first is Yakupov, and he’s really the only stinker in the bunch. Yes, it’s a gamble, but based on the last fifteen years, there are very good odds that you’re going to get a very good player — at worst.

  • #97Train/McDavidCopperfield

    Totally unrelated to the article, but look at the left draft pane vs the right in the article’s leader image above. Of the 15 players drafted in the left pane, I recognize 14 of them as impact players in the league. Compared to the right pane, there’s what? Two players. Just a neat observation as to the players the Leafs could be drafting with these high picks in the next couple years and the difference between the top 15 picks vs. the bottom 15…

  • Bob Canuck


    Thanks for the post; hindsight bias is factor that we should always consider when performing analysis.

    However, I should point out that the Schenn draft selection predated the Burke regime. I note your error with the benefit of hindsight and a bias for facts.

    Cheers! ?