He might prefer to exit sooner.
Victor Oladipo looking to move on this offseason, according to sources
The Pacers control the situation for now. Oladipo is under contract next season at $21 million. But the specter of him leaving in 2021 unrestricted free agency applies implicit pressure. Indiana could trade him rather than risk him walking for nothing.
Of course it’s not fait accompli Oladipo would leave the Pacers in 2021 free agency. They’re looking for a new coach, and maybe that hire would help motivate Oladipo to stay. Indiana could take the upcoming season to sell him on a new direction. If going that route, the Pacers could still pivot before the trade deadline. That plan would allow Oladipo time to get healthy and boost his trade value (or suffer a setback and tank his stock).
Oladipo’s impending free agency also gives him some leverage in trade talks. He can signal an intent to re-sign with only certain teams, motivating those teams to trade for him (and dissuading other teams).
But at this stage, even if Oladipo is ready to leave, Indiana still holds most of the cards.