Leafs Trade Speculation: The Good, the Bad and the Ugly

James van Riemsdyk (21) who came to Toronto as a result of a very successful trade, is often the subject of Leafs Trade Speculation --- Mandatory Credit: John E. Sokolowski-USA TODAY Sports
James van Riemsdyk (21) who came to Toronto as a result of a very successful trade, is often the subject of Leafs Trade Speculation --- Mandatory Credit: John E. Sokolowski-USA TODAY Sports /

An integral part of being a die hard fan of the blue and white is participating in Leafs Trade Speculation. Unfettered from such restraints as the availability of the targeted players, willing trade partners and sometimes reality itself, the self appointed armchair GM can pretty much do anything he or she wants to on the imaginary trade front.

Some trade proposals made by fans are flat out crazy, while other deal suggestions can run the gamut from completely lopsided in favor of the Leafs, through deals that sort of make sense to the rare mock transaction that is surprisingly astute. In even rarer instances, trade speculation actually comes to fruition, presumably taking place as a matter of coincidence or by accident, rather than as a result of any insight or insider knowledge held by the speculator.

The old adage that states “even a broken clock is right twice a day” seems to be apropos when accuracy occurs and maybe is even indicative of the frequency with which armchair GMs get it right. That would be getting it correct two times out of 86, 400 attempts (based on the number of seconds in a day) or odds of 43, 200 to one if you prefer. As unscientific as arriving at these odds in this manner may be, the notion of once in a very big number of occurrences that fan-based Leafs trade speculation is actually substantive, sounds about right.

In other words we get it wrong thousands of times more often than the precious few times we get it right but this doesn’t stop us from enthusiastically returning to the fray the very instant we catch a whiff of news concerning a good player we would like to see in a Leaf uniform becoming available. No trade or no movement clauses, Cap considerations and even roster sizes be damned, we want that player on our team.

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The necessity of the GM for the trading partner organization losing his mind as he concludes a woefully one-sided deal in our favor is simply not our concern. His NHL salary surely allows him the resources to pay for the therapy he will need to get over it, that is until the next time we deal with him and fleece him mercilessly yet again. (Insert villainous laugh here.)

Such are the machinations involved with the internal workings in the mind of the armchair GM during bouts of imaginary Leafs trade speculation.
It seems to matter not that the proverbial heist of uneven player transactions between two NHL franchises is so rare that it is truly an historical anomaly. If we look at Leaf history alone, since the beginning of the 1960’s we can find a handful of trades that we have arguably won hands down, but just two that would fit the description of being lop-sided in our favor.

The first of these two uneven trades was orchestrated by Punch Imlach, where on February 10, 1960 he offered up marginal NHL player Marc Reaume for Red Wings all star defenceman Red Kelly. As a straight up trade it would have been absurd, but of course there is more to the story.

Kelly had just been traded a few days earlier by Detroit to the New York Rangers but failed to report, choosing retirement instead. The Red Wings accepted Reaume unconditionally, whether Imlach talked Kelly out of retirement to play for the Leafs or not.

The way the story is told in Leaf lore today however, Imlach was the greatest of all NHL General Managers among his contemporaries, shrewder than all of his peers. Such is the way that winning a trade is treated with the passage of time. The story simply would have been buried and long forgotten if Kelly had remained retired, while Reaume was given up for nothing.

The next big trade that went tremendously well for the Leafs is of course the January 2, 1992 Gary Leeman five-player package to the Calgary Flames for the Doug Gilmour five-player package to the Leafs. Summarized as follows:

The Best Trade Deal in Leafs History
January 2, 1992
To TorontoTo Calgary
  • Doug Gilmour
  • Jamie Macoun
  • Kent Manderville
  • Ric Nattress
  • Rick Wamsley
  • Gary Leeman
  • Craig Berube
  • Alexander Godynyuk
  • Michel Petit
  • Jeff Reese

A number of other trades could all warrant special mention status for how well they worked in our favor. There are also the trades we would like to forget, but who amongst us can?

Tuukka Rask
Apr 7, 2016; Boston, MA, USA; Boston Bruins goalie Tuukka Rask (40) squirts himself with water during the first period against the Detroit Red Wings at TD Garden. Mandatory Credit: Bob DeChiara-USA TODAY Sports /

The player swap that sent Russ Courtnall to our arch enemy the Montreal Canadiens for John Kordic on November 7, 1988 is another trade we would all like to forget, but after that the list of horrible trades made by the Leafs begin to be viewed in a different light.

Of the two major categories we can place most bad hockey trades in, these first two mentioned fall into Category One: “Management, What were you thinking?”

The other grouping could be called Category Two: “Hindsight may be 20-20 but that trade sure didn’t work in our favor”.

On a related topic, I refuse to count what another team did with the draft pick they received in a trade with the Leafs as even a qualifier for a bad trade. This is based on a very simple premise in that there is no counterbalance in this type of trade discussion.

Most draft picks don’t make it to the NHL, this is even true of first round picks outside of the top ten. My point as it pertains to Leafs trade speculation will become evident in a moment but first ….

A challenge:

Name one, just one player acquired with a first or second round pick the Leafs have traded that was a major flop and never skated in the NHL for the team that drafted them.
….. why is it that of even the most ardent of fans, most people cannot do this?

They always seem to be able, with the assistance of Leaf bashing hockey pundits, to name the draft picks traded away by the Leafs that made it to the NHL and had success but never the wasted picks. Like I said, there is no counterbalance to this discussion, it always seems to be comprised of a series of “what ifs” over players we could have drafted instead of trading the pick.

Now, let us make this challenge just a bit more difficult.

Look to the 2018 NHL entry draft as of today and pick an All-Star defenceman in the first round. You do not know where you will be picking until the end of the 2017-18 season, but because you received your first round pick from a struggling team, assume it is likely going to be in the top five overall.

What’s the matter? … would a magic eight ball help … Or some mystic tea leaves perhaps?

Do you view this challenge as a ridiculously impossible feat of fortune telling, which if somehow successful, could only have been achieved through blind dumb luck? Of course it is impossible but let me explain my point.

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Back on October 16, 1989 there was a trade made by then Leafs General manager Floyd Smith with the New Jersey Devils to acquire defenceman Tom Kurvers. The price was the Leafs’ 1991 1st round pick, which was by all measures an over-payment based on over-valuing Kurvers’ talents but that is all it was.

At the time, no one outside of Kamloops BC had even heard of the player who was chosen with that pick almost two years later. His name was Scott Niedermayer and he had just begun the first month of his major junior career at the time of the transaction.

The Leafs did not trade Neidermayer for Kurvers! …at least not in the real world.

There have been plenty of instances over the past few decades where weeping into one’s beverage has been the appropriate response to moves made by Leafs management. There is no need to contrive or dream up even more bad deals by adding “what ifs” to the equation.

Next: Forward Combinations, Who Will be Traded First?

Besides, who has time? Just like all other Armchair GMs, I am intent on saving the Leafs franchise single-handedly with my brilliant trade strategies.

How about yourself? What type of Leafs trade speculation have you come up with? Are there any players you would like to see the Leafs acquire? . . . or send packing?