Judging a trade can be tricky business. It’s especially difficult to gauge winners and losers in a trade when the parameters involved offer varying degrees of benefit to the parties involved.
Personally, when it comes to measuring trade value in the immediate versus the longrun, I like to think about the Todd Van Poppel rookie card I swapped back in 1991. Van Poppel was supposed to be some kind of pitching phenom. I was too young at the time to understand or investigate why such sentiment was so popular, but I bought in. I scored a Van Poppel rookie card in a pack of Score baseball cards one afternoon. Knowing that such a card was a valuable commodity at the time, I used it to complete my set of 1990-91 Upper Deck hockey cards. Jeremy Roenick’s rookie card was featured in said set, and it just so happened to be the final piece of cardboard I required to complete my collection.
One afternoon, at the age of 11, I wandered in to my local card shop and presented the owner with my Todd Van Poppel rookie card. I told the man at the counter that all I wanted was the 1990-91 Jeremy Roenick card. I can’t recall what the value of these cards were at the time, but I know that this older gentleman looked at me and didn’t think twice about ripping me off. We had a deal. I had my Roenick rookie card to finish off my inaugural Upper Deck hockey set, and card store guy had his 25th Van Poppel rookie to add to his collection for the purpose of cashing in at the end of Van Poppel’s illustrious career.
Todd Van Poppel flamed out famously in the Majors. My 1990-91 Upper Deck hockey collection sits in a Rubbermaid container in my parents’ basement and I’ve seen its current sale value as low as $3.99 and as high as $19.99. Whatever the case, I won that trade, but it wasn’t a certain victory until four or five years after the fact.
This may not seem relevant at all here on Backhand Shelf, but it’s remotely relevant when we consider the Phil Kessel-for-Maple Leafs draft picks trade. Brian Burke gambled when he shipped three draft picks to the Boston Bruins in exchange for Phil Kessel back in 2009. He gambled that the pieces already existing on the Maple Leafs roster before he took over, combined with the free agents he had brought in, would make for a legitimate contender with the addition of Kessel. It didn’t work out right away, but here we are looking at a Game 7 between these two teams nearly five years after the fact. Brian Burke is no longer present in this picture, but his finger prints are smeared all over it.
Below is a timeline of the Kessel trade and the events that took place in its aftermath, complete with facetious judgment on who held the upper hand at the time. Read the rest of this entry »

