Year signed: 2013
Team: Toronto Maple Leafs
Contract: 7 years, $36.75 million
ROI: Clarkson scored just 15 goals in 118 games with the Leafs.
Bottom line: This is considered the worst contract in Maple Leafs history, which is saying something.
It's not to say that Clarkson wasn't a solid player. When the hard-nosed winger hit the open market in the summer of 2013, the speculation was that as many as 20 organizations showed interest.
But committing seven years to a merely solid 29-year-old was a mistake from the beginning. This, compounded by injuries, resulted in Clarkson scoring just 15 goals in two seasons with the Leafs.
Toronto traded Clarkson to Columbus in 2015 for Nathan Horton. It was an exchange of bad contracts — the injured Horton never suited up for the Maple Leafs. Clarkson played just 26 games for the Blue Jackets, before they passed on his poison pill contract to the expansion Golden Knights.
The injured Clarkson never played for Vegas.
But what goes around comes around. In 2019, Vegas sent Clarkson's contract back to Toronto. In a convoluted, but clever bit of salary cap manipulation, Clarkson and Horton's contracts (Horton is still on the books, too) will give the Maple Leafs more cap space in 2019-20.
Meanwhile, for Clarkson, it doesn't matter who's cutting his checks — he's still getting them. He's now the coach of his local high school hockey team.