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Cleveland Cavaliers could fix all-time NBA Draft mistake with free agency signing 12 years later

Originally posted on NBA Analysis Network
By Jonah Kubicek | Last updated Jul 21, 2025 6:30 PM ET

12 years after drafting Anthony Bennett first overall, the Cleveland Cavaliers finally have a chance to redeem themselves with an overlooked free agent signing.

The 2013 NBA Draft was one of the worst draft classes of all time. Only Giannis Antetokounmpo, Rudy Gobert, and Victor Oladipo made an All-Star appearance, and first overall pick Anthony Bennett is considered the biggest bust in NBA history.

Bennett played in only 52 games for the Cleveland Cavaliers, averaging 4.2 points and three rebounds. While there was no consensus top pick, the Cavs originally wanted to select Oladipo, and might finally have a chance to add him to the roster.

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Oladipo is drawing free agency attention

Oladipo has not played since 2023, but he is only 33 years old and was one of the best two-way guards during his prime. A team like the Cavs, looking to bolster their depth, might be interested in signing him.

During the Las Vegas Summer League, Oladipo held a public workout, which was attended by multiple NBA teams.

“A member of the front office was in attendance for Victor Oladipo’s recent Vegas-based workout,” reported Cavaliers’ insider Chris Fedor. “Oladipo, 33, is trying to resuscitate his NBA career, proving to NBA decision-makers that he is healthy and can still be effective.”

The Cavs added Lonzo Ball this summer and boast a solid backcourt rotation of Ball, Darius Garland, and Donovan Mitchell. However, they still have four open roster spots, and Oladipo would be a low-risk addition.

Cavaliers have long coveted Oladipo

After LeBron James made his Decision and signed with the Miami Heat in 2011, the Cavaliers started looking for a new franchise player. In 2011, they landed the first overall pick, nabbing Kyrie Irving, who quickly emerged as a centerpiece in the backcourt.

The Cavs would go on to pick Bennett and Andrew Wiggins first overall in future drafts, although Wiggins was later traded for Kevin Love.

After James returned in 2015, the Cavs made four Finals in a row, beating the Golden State Warriors only once.

Had they had Oladipo in their backcourt next to Irving, they may have had an answer on defense for Stephen Curry. Between 2015 and 2018, he averaged 1.7 steals and spaced the floor rather well, and could have been the missing link Cleveland needed to come out on top more often than not.

The Cavs were high on Oladipo in 2013, although they made a last-minute decision to draft Bennett instead, a decision that haunted the franchise.

“Cavs chairman Dan Gilbert was once a massive Oladipo fan, eager to select the bouncy Indiana star with the first-overall pick in the 2013 NBA Draft,” Fedor continued. “David Griffin, assistant general manager at the time, campaigned for UNLV’s Anthony Bennett.”

The Indiana Pacers and Phoenix Suns have also been linked to Oladipo, although Cleveland can offer him the best chance at postseason success.

This article first appeared on NBA Analysis Network and was syndicated with permission.

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