Twelve years after first drafting Anthony Bennett, the Cleveland Cavaliers finally got the opportunity to redeem themselves with an overlooked free agent signature.
The 2013 NBA Draft was one of the worst draft classes ever. Only Giannis Antetokounmpo, Rudy Gobert and Victor Oladipo appeared in the All-Stars, with the first pick Anthony Bennett being considered the biggest bust in NBA history.
Bennett played only 52 games for the Cleveland Cavaliers, averaging 4.2 points and three rebounds. There was no top pick for consensus, but Cavs originally wanted to choose Oladipo, but they may have the opportunity to add him to the roster in the end.
Oladipo hasn’t played since 2023, but he was only 33 years old and one of Prime’s best two-way security guards. Teams like the Cavs are trying to strengthen their depth, but they may be interested in signing him.
In the Las Vegas Summer League, Oladipo held public training with multiple NBA teams involved.
“Front Office members were attending Victor Oladipo’s recent Vegas-based training,” reported Cavaliers insider Chris Fedor. “Oladipo, 33, is trying to revive his NBA career and has proven to NBA decision makers that he is healthy and still effective.”
This summer, Cavs added Lonzo Ball and boasted solid backcourt spins of Ball, Darius Garland and Donovan Mitchell. However, there are still four open rosters, and Oladipo will be a low-risk addition.
After LeBron James made his decision and signed with the Miami Heat in 2011, the Cavaliers began searching for a new franchise player. In 2011 they landed their first overall pick. Kyrie Irving quickly emerged as the center of the backcourt.
Cavs continued to pick Bennett and Andrew Wiggins in the overall first choice in future drafts, but Wiggins was later traded for Kevin Love.
After James returned to 2015, the Cavs continued their four finals, beating the Golden State Warriors only once.
If they had Oladipo in the backcourt next to Irving, they might have had the answer about Stephen Curry’s defense. Between 2015 and 2018, he stole an average of 1.7 steel and spaced the floors quite well, which could have been missing the links needed to make Cleveland come out frequently.
The Cavs were high in Oladipo in 2013, but instead made the last-minute decision to draft Bennett, but the decision that bothered the franchise.
“Cavs’ Chairman Dan Gilbert was once a massive Oladipo fan and was keen to pick a resilient Indiana star on the first pick in the 2013 NBA Draft,” continued Fedor. “David Griffin, then assistant general manager, campaigned for Anthony Bennett at UNLV.”
The Indiana Pacers and Phoenix Suns are also linked to Oladipo, but Cleveland can offer the best chance of postseason success.

