Oladipo, who is entering a contract year, has become a frequent subject of trade speculation in recent months, since it’s unclear whether he’ll remain in Indiana beyond his current contract. A report earlier this week suggested the two-time All-Star likes playing with the Pacers and would be happy to sign a big new deal with the team, but an earlier story had indicated he may be “looking to move on” from Indiana.
The Bucks, meanwhile, will be seeking out roster upgrades this offseason as they attempt to boost their title chances following a disappointing second-round playoff exit and convince Giannis Antetokounmpo to sign a long-term contract with the franchise. Chris Paul has been mentioned as one possible target for Milwaukee, though a September report stated that the club is “highly unlikely” to aggressively pursue the veteran point guard.
While Oladipo would be an intriguing addition to an already formidable Bucks defense, his offsensive game didn’t look quite right in 2019/20 as he returned from the quad tendon injury that sidelined him for a full year. If he could recapture his form from the previous two seasons – when he averaged 21.7 PPG and 4.6 APG on .461/.362/.780 shooting – he may be just the sort of play-maker, scorer, and shooter that Milwaukee needs in its backcourt.
Any Bucks offer for Oladipo would probably have to start with point guard Eric Bledsoe for salary-matching purposes and would likely see the Pacers’ 2020 first-round pick returned to Indiana. I imagine the Pacers would seek another future first-round pick or other additional assets for Oladipo, while the Bucks may be reluctant to go all-in on a player who didn’t look fully healthy in ’19/20.
The Pacers and Bucks, two Central rivals, did come together last year to complete a sign-and-trade involving Malcolm Brogdon, so respective heads of basketball operations Kevin Pritchard and Jon Horst have worked with one another before.