The 30 most painful NBA Draft pass-ups since 2000

NBA Draft Mistake #29: The L.A. Clippers drafting Darius Miles over Mike Miller and Jamal Crawford.

In the 2000 NBA draft, the Los Angeles Clippers took a risk by drafting Darius Miles third out of high school. At the time, no high school player had ever been taken that high, but Miles’ size, athleticism, and raw talent won out. While he wasn’t as big of a disappointment as others on this list, it is fair to say that his career didn’t go as expected. Miles spent two decent seasons with the Clippers, coming off the bench, before being traded in a deal that included Andre Miller.

As it turns out, the Clippers got rid of Miles just in time before they really regretted their decision. He spent time in Cleveland before ending up with the Portland Trailblazers. After signing a huge contract, he later missed two full seasons recovering from microfracture surgery before being waived and his contract removed from Portland’s books.

That led to a strange saga where Portland then threatened to sue teams if they signed him during a comeback attempt. He did, resulting in them being stuck paying him. No matter what, Miles being taken third didn’t work out, and while the 2000 NBA draft was awful, there were still better players on the draft board. Mike Miller and Jamal Crawford, neither of whom were all-stars, both had long careers and were less risky than Miles was.