Perhaps no NHL team has made a living off of making unconventional and unlikely trades in recent years as the Pittsburgh Penguins have.
Take the Phil Kessel acquisition in 2015 — Kessel was carrying a $8.0 million salary cap hit, the Pens are perpetually cap-strapped right up against the upper limit. The thought of being able to trade for such a high-priced winger seemed pure fantasy. But Pittsburgh got creative (and utilized the good fortune of Toronto wanting to dump Kessel badly) by having the Maple Leafs retain $1.