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While it's somewhat depressing to say, the day the Leafs traded David Clarkson might be one of the five best days to be a Leafs fan in the last decade. It really can't be overstated how awful and seemingly untradeable that contract was. At the time of the trade, Clarkson still had 5 full years remaining on his deal with an AAV of 5.25M.
He had just come off a season where he scored 11 points in 60 games, playing 2nd line minutes with Nazem Kadri and Joffrey Lupul, and getting PP time too.