The 1st annual Jimmy Awards: 10 worst contracts in the NBA

There are more terrible contracts in the NBA than in every other sport combined. Parsing through them to find the 10 worst was tough, but it had to be done

Momentary lapses of judgment leading to bad decisions. It happens every day to all of us. And every one of them seems like a good idea at the time.

Here’s the thing though: unlike ordering oysters at a diner, when an NBA GM makes a bad decision, it haunts the franchise that employs him for years. Even one truly heinous contract can single-handedly derail the results of several good moves made around it.

That almost imperceptible moan you just heard? That was Knicks fans everywhere wincing in pain, which is why this column is named after their owner, who has signed more terrible contracts than anyone.

(Somewhere, deep in the woods, Jim McIlvane got really excited when he thought this column was named after him. Don’t worry Jimmy, we will never forget you!)

There is no exact science to ranking the worst NBA contracts, but there is one major thing to keep in mind: length is everything. A terrible player making a ton of money on an expiring contract is less onerous than a slightly less terrible player making slightly less money but signed for multiple years.

One more thing: context matters.

You won’t see JR Smith on this list because his shooting and passable defense are key to Cleveland’s chances every June. If he was signed to the same deal in, say, Charlotte, he might have made the cut here.

Honorable mention to Jon Henson, Myers Leonard, Omer Asik, Solomon Hill, and towel-waivin’ Kyle Singler.