Oladipo last played in the NBA in 2023 with the Miami Heat. He sustained a devastating left patellar tendon injury during the Heat’s 121-99 Game 3 win over the Milwaukee Bucks in the first round of the playoffs, sparking speculation about whether his career might be nearing its end after a string of injuries.
His injury history is lengthy. In January 2019, Oladipo ruptured his right quadriceps tendon, an injury so severe that he was unable to play in the NBA for more than a year. He underwent season-ending surgery on that tendon in May 2021 and was sidelined for almost another year. In 2023, a new injury derailed his momentum. He was traded several times during rehab and found himself without a team after the Memphis Grizzlies waived him in February 2024.
Despite the setbacks, Oladipo did not quit. He appeared to be on track for another NBA opportunity in 2025. ESPN reported that Oladipo participated in a private workout in Las Vegas in July 2025, attended by personnel from multiple NBA teams. Although he impressed during the session, no team ultimately offered him a contract at that time.
In November 2025, Oladipo joined the G League’s Wisconsin Herd. During the 2025-26 season, the 34-year-old posted averages of 13.5 points, 4.6 rebounds, 3.8 assists, and 2.1 steals per game for the Herd before being traded to the Cleveland Charge in February 2026. He did not play for the Charge.
Looking back at Oladipo’s journey, it’s clear the road has been challenging. Once the No. 2 overall pick in the 2013 NBA Draft by the Orlando Magic, he showed promise with solid seasons that led to a trade to Oklahoma City in 2016. A subsequent move to Indiana in 2017 yielded his peak years, including All-Star selections, an All-NBA Third Team nod, and the 2018 Most Improved Player award. He earned All-Star honors again in 2019, but a series of injuries limited his impact and availability, leaving his ultimate height in question.
Oladipo’s career highlights the volatility of professional sports, where talent can be tempered by injuries, but the tenacity to return remains a defining trait. As he continues to pursue opportunities, teams weighing a potential fit will consider his experience, leadership, and demonstrated resilience.
