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Cleveland Cavaliers’ 10 biggest draft busts since 2000

By Caleb Crowley

NEW YORK, NY - JUNE 27: Anthony Bennett of UNLV poses for a photo with NBA Commissioner David Stern after Bennett was drafted #1 overall by the Cleveland Cavaliers during the 2013 NBA Draft at Barclays Center on June 27, 2013 in in the Brooklyn Bourough of New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Mike Stobe/Getty Images)
NEW YORK, NY - JUNE 27: Anthony Bennett of UNLV poses for a photo with NBA Commissioner David Stern after Bennett was drafted #1 overall by the Cleveland Cavaliers during the 2013 NBA Draft at Barclays Center on June 27, 2013 in in the Brooklyn Bourough of New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Mike Stobe/Getty Images) /
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Cleveland Cavaliers
Dylan Windler, Cleveland Cavaliers. Photo by Jason Miller/Getty Images /

7. Dylan Windler, 2019 – Rd 1, Pick 26

Dylan Windler may be the biggest “What If” selection in the modern Cavaliers era. Windler has all the makings of a prototypical, high value 3-and-D forward. Sadly, his career was immediately sidelined by recurring injuries, leaving Windler only to appear in a total of 84 NBA games spanning over three seasons. When he did manage to step on the court, his potential and talent was undeniably present. His shooting was solid, and his defense was above average.

But, whether or not Windler can reach his potential will probably never be realized. This past offseason, the Cavaliers did not extend a qualifying offer to Windler, and no NBA team has offered him a full NBA deal. He did sign a non-guaranteed two-way contract with the New York Knicks eventually, though he is unlikely to spend much time outside of the G-League.

6. DeSagana Diop, 2001 – Rd 1, Pick 8

DeSagana Diop may have the most confusing career on this list. Selected in the top 10, Diop never became more than a last man on the roster. Over his 12-year career, Diop averaged 2 points, 3.7 rebounds, and shot 46.7 percent from the free throw line. His career high points average was 2.9 on 16.4 minutes per game in the 2007-08 season. Even with his disappointing numbers, Diop managed to stick around in the Association for over a decade, albeit on small contracts with half a dozen rosters. Staying in the NBA at all, however, is something many others on this list could not accomplish.

The 7-foot center could not contend in the league at all, and the Cavaliers surely regret the selection, considering the amount of incredible talent selected after him. Zach Randolph, Gerald Wallace, Tony Parker, and Gilbert Arenas were all still available when Cleveland chose Diop. Only in dreams can the world consider what would have transpired for the Cavaliers if they had chosen Tony Parker only to draft LeBron James two years later. The missed potential not only for Diop, but the entire franchise, makes for a horribly depressing thought.

5. Christian Eyenga, 2009 – Rd 1, Pick 30

Following a similar thread with many others, Christian Eyenga entered the NBA nearly as quickly as he exited. Eyenga was not considered a fully realized prospect in 2009, but his defensive prowess as a quick shot blocker and decent offense made Eyenga an eye-catching prospect to pair alongside LeBron James. At this point, the Cavaliers were consistently competing with the top teams in the East in the playoffs. They were unlikely to find a second star in the latter parts of the draft, but they failed even to find a steady role player most times.

Once again, the Cavaliers could have done much better in the draft but made mistakes. Other than Patrick Beverly, there were not many options in the draft decidedly better that the Cavaliers skipped. They did, however, draft eventual three-time NBA champion Danny Green in the second round only to trade him near instantly. The constant blunders by Cleveland in the first LeBron era makes it no wonder that he eventually left.