14. Cleveland Cavaliers – 1989
The Cavs had an amazing opportunity in 1989 to break their championship slump. But they fell short in the first round against the Bulls. This series also confirmed that Michael Jordan was the real deal. The young man was impressive against Cleveland the previous year, but rose to a new level throughout this history-making series.

He scored 50 points in Game Four but was a high-scoring threat throughout the entire series. In the end, the Cavaliers couldn’t handle him and the red-hot Bulls. Perhaps it’s unfair to call it a choke job because of the context. But it was a major upset at the time (via Yahoo!)