Throughout the process, the Pacers have stated that retaining Oladipo is a priority and have shown signals that they’ll do all they can to make it happen. They were even willing to pay him the remainder of his 2019/20 salary when he initially planned on opting out of the summer restart to focus on his health, despite the fact that he’d received medical clearance from doctors.
But if Indiana knows Oladipo plans to leave in free agency in 2021, it’s in the organization’s best interests to see what it can get for him before then rather to resign itself to losing him for nothing. The Pacers’ willingness to take that route with Paul George was the reason the team landed Oladipo (and fellow All-Star Domantas Sabonis) in the first place.
The challenge for the Pacers if they explore the trade market for an Oladipo deal will be finding a trade partner willing to give up a package that reflects the guard’s pre-injury value. Since Oladipo returned from his torn quad tendon in January, he hasn’t quite looked like the same player — in 19 games this season, he averaged just 14.5 PPG on .394/.317/.814 shooting.
Questions surrounding Oladipo’s health and production going forward will complicate any trade talks, especially if suitors believe they’ll have a shot to sign him outright in free agency a year from now. As such, an offseason trade definitely isn’t a sure thing.
In fact, sticking with Oladipo and hoping he looks like his old self to start next season may end up being Indiana’s best strategy. If Oladipo alleviates his health concerns in the first half, the Pacers could potentially extract more value for him at the trade deadline than they could this offseason — especially if multiple contenders view him as a missing piece for the stretch run.