Report: Cavs linked to Victor Oladipo, who once had a ‘massive’ fan in Dan Gilbert

Victor Oladipo hasn’t played in the best basketball league in the world since he suited up in two games for the Miami Heat in the 2023 NBA Playoffs, yet at the age of 33, he’s attempting to make a professional comeback.

Oladipo recently worked out in Las Vegas in front of people in NBA circles, and according to Cleveland.com’s Chris Fedor, a member of the Cleveland Cavaliers’ front office was among the folks in attendance for Oladipo’s workout.

Cavaliers owner Dan Gilbert was allegedly once a “massive” fan of Oladipo’s, too.

“The Cavs will remain opportunistic, always looking for potential improvements,” Fedor wrote. “Does an unforeseen maneuver pop up over the next few months? Hard to predict.

“A source tells Cleveland.com that a member of the front office was in attendance for Victor Oladipo’s recent Vegas-based workout. Oladipo, 33, is trying to resuscitate his NBA career, proving to NBA decision-makers that he is healthy and can still be effective.

“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 — until David Griffin, assistant general manager at the time, campaigned for UNLV’s Anthony Bennett. The rest is history.

“Could Gilbert get his man more than a decade later? Does Oladipo fit?”

Gilbert likely wishes he could go back in time so that the Cavaliers could draft Oladipo instead, as the guard was a bona fide star in his prime. His best season came in the 2017-18 campaign when he averaged a career-high 23.1 points per game and was named an All-Star.

Bennett, meanwhile, proved to be one of the biggest draft busts in modern NBA history. He lasted just one season in Cleveland and hasn’t played in the league since the 2016-17 campaign.

It’s of note that Oladipo’s former team, the Heat, have been linked to him in rumors lately as well. Per Ira Winderman of the Sun Sentinel, the Heat were one of the teams in attendance for a scrimmage Oladipo participated in earlier this month.

If Oladipo is hoping to finally win an NBA title in the coming season, the Cavaliers stand out as clearly the more appealing option of the two landing spots.

After all, the Heat just recently were swept in the opening round of the 2025 NBA Playoffs by the Cavaliers. Cleveland won 64 games in the 2024-25 regular season and ended up with the second-best record in the entire league.

Oladipo has been part of a deep playoff run before, and his playoff experience could come in handy for the Cavaliers if he can avoid the injury bug. He was an integral part of the Heat team that made a run to the Eastern Conference Finals in the 2022 NBA Playoffs.

It will be interesting to see if Oladipo ends up with an NBA team for the 2025-26 season.