The Cleveland Cavaliers don't exactly have a rich history. However, they turned things around after the arrival of LeBron James followed by the current era that has propelled the franchise back to relevancy. After a disappointing second-round exit at the hands of the Indiana Pacers, the Cavs will look forward to the offseason to make some potential upgrades. One route could be through the upcoming 2025 NBA Draft, where the team will be selecting twice in the second round with the 49th and 58th picks.
Although Cleveland has acquired some great prospects through the draft, that hasn't always been the case. Here is a look at the Cleveland Cavaliers' 10 worst NBA Draft day mistakes in history.
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10. Christian Eyenga – 2009

While expectations are much lower on late first-round picks, that's not an excuse to waste one. At the 2009 NBA Draft, the Cavs selected Christian Eyenga out of Congo with the 30th overall pick. Eyenga was expected to inject some defensive prowess to help LeBron James. However, he failed to be productive at the NBA level, averaging just 6.2 points per game in a Cavs uniform. His NBA career ended after just two years.
9. Sergey Karasev – 2013

Another international prospect who didn't pan out with Cleveland is Sergey Karasev. The Russian forward was picked 19th overall at the 2013 NBA Draft. Standing at 6-foot-7, Karasev had size and the ability to space the floor. However, playing for a cellar-dwelling Cavs squad didn't do him any favors. In fact, he averaged just 1.7 points per game for Cleveland. Karasev still managed to enjoy a two-year tenure with the Brooklyn Nets before taking his talents back to Europe.
8. Dion Waters – 2012

Dion Waters turned out to be a decent scorer at the NBA level. But in hindsight, he shouldn't have been drafted as high as the fourth overall pick of the 2012 NBA Draft. While he could score, Waiters wasn't exactly the star the Cavs needed to successfully rebuild, especially when looking at the players drafted after him. The list includes the likes of Damian Lillard, Draymond Green, and Andre Drummond.
7. Trajan Langdon – 1999

Another wasted lottery pick came at the 1999 NBA Draft for the Cavaliers when they picked Trajan Langdon. The Duke standout's best arsenal was 3-point shooting. Although shooting was his calling card, Langdon wasn't exactly good at anything else. By not developing other facets of his game, Langdon was gone from the NBA after three seasons with Cleveland. On the bright side, he did enjoy a fruitful career in Europe.
6. Vitaly Potapenko – 1996

A Ukrainian player out of Wright State, Vitaly Potapenko was expected to bolster the Cavs' front court by forming a twin-tower combination with Zydrunas Ilgauskas. He was drafted with the 12th overall pick at the 1996 NBA Draft, one pick ahead of the late Kobe Bryant. Unfortunately, Potapenko's game didn't translate well in the NBA. He averaged just 6.7 points per game for the Cavaliers in three seasons before embarking on a journeyman career.
5. J.J. Hickson – 2008

J.J. Hickson was another player that the Cavs hoped to develop into a major contributor alongside James. He was athletic enough to throw it down while possessing the motor to gobble up rebounds. However, the 19th overall pick of the 2008 NBA Draft struggled to stay consistent in his Cavs tenure.
Article Continues BelowFurthermore, with the selection of Tristan Thompson, who was more consistent and turned out to be a major contributor to Cleveland's 2016 championship run, Hickson eventually parted ways with the organization. He played for a handful of NBA teams before playing professionally overseas.
4. Luke Jackson – 2004
One year after making James the top overall pick of the draft, the Cavaliers possessed the 10th overall pick of the 2004 NBA Draft. Thanks to his elite shooting and decent passing at the college level, Cleveland chose Luke Jackson out of Oregon.
Unfortunately, he was unproductive at the NBA level, averaging just 2.7 points per game for the Cavs. It made fans wonder what if the franchise selected better players such as Al Jefferson, Trevor Ariza, Tony Allen, or Jameer Nelson. While not exactly superstars, any of them would've contributed more alongside The King.
3. DeSagana Diop – 2001

DeSagana Diop was a menace at the high school level while playing for Oak Hill Academy. He instantly made the jump into the NBA as he was selected with the eighth overall pick at the 2001 NBA Draft. However, Diop never acclimated well to the NBA. In fact, throughout his career, Diop never averaged more than 3.0 points per game in a season. But on the bright side, despite his production, the Senegalese big man found a way to stick in the NBA for more than a decade.
2. DaJuan Wagner – 2002
A year after drafting a disappointing Diop, the Cavs made another costly mistake by selecting DaJuan Wagner. He was an absolute star for Memphis, convincing the Cavs to use their sixth overall pick of the 2002 NBA Draft on him. Although Wagner had a decent rookie season, it was downhill from there. To make matters worse, health concerns started to derail his career.
1. Anthony Bennett – 2013

The biggest bust in recent memory goes to Anthony Bennett. The Canadian prospect out of UNLV had size and skills that made him a decent player at the college level. By making him the top overall pick of the 2013 NBA Draft, Cleveland believed that he was a franchise building block.
However, he ultimately failed to live up to lofty expectations. After good stints at the NBA Summer League and the preseason, Bennett's flaws were exposed, and the Cavaliers were given a slap of reality that convinced them to give up on Bennett just after one season. In fact, Bennett became the first lottery pick since Hasheem Thabeet to be demoted to the NBA G-League.