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Mailbag: Could Victor Oladipo join the Cavs?

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Cleveland could be wheelin’ and dealin’ this offseason.

Indiana Pacers v Cleveland Cavaliers Photo by David Liam Kyle/NBAE via Getty Images

Dude from the Athletic mentioned Oladipo and Turner might both want out of Indy, and mentioned a swap of those two for Hayward + assets as a potential trade scenario. That’d make the Celtics pretty terrifying, especially defensively, even if Oladipo sucks. If he doesn’t suck they’d be East favs. On that note, would Oladipo be worth taking a flyer on? From SaintWeirdo3

There’s a lot to unpack with this question so let’s take it piece by piece. First off, it’s been reported by multiple outlets that both Victor Oladipo and Myles Turner would both prefer to be traded from Indiana this offseason. According to league sources, those reports are very true and Oladipo especially wants to start fresh with a new organization. Those same sources shared that both Oladipo and Turner have soured on the direction of the team after the Pacers parted way with Nate McMillan after their first-round loss to the Miami Heat. Oladipo also wants a maximum contract, despite looking sluggish after suffering a severe injury, and Indiana is unwilling to commit that type of money to their star at the moment.

With that in mind, it seems that the Pacers have made both Oladipo and Turner available on the trade market, per league sources. According to those same sources, a handful of teams around the league have shown interest in Turner — including the Golden State Warriors. A hypothetical trade of Turner to Golden State for Andrew Wiggins and the no. 2 pick in the 2020 NBA Draft makes a ton of sense. The Warriors can add the perfect center to their starting lineup and the Pacers can rebuild around a prospect like James Wiseman or LaMelo Ball.

Oladipo, meanwhile, has a few interested suitors including the New York Knicks and the Boston Celtics. The Knicks are beyond desperate to be relevant in the grand scheme of the NBA - even more so in New York with Kyrie Irving and Kevin Durant returning to the Brooklyn Nets next year. Trading for a star like Oladipo would be a step in that direction. But, the Knicks, much like the Pacers, are hesitant to commit a serious amount of scrilla to Oladipo due to concerns with his health, according to league sources. It’s still the Knicks, though.

The hypothetical offer mentioned above that has the Celtics sending Hayward and future picks for Oladipo also does make some sense. It would be nice to finally rid of Hayward’s albatross of a contract. But, it all hinges on Oladipo’s health for the trade to happen. Danny Ainge is known for dealing with damaged goods (Isaiah Thomas to Cleveland) but, he might be averse to adding on another disgruntled player that’s injury-prone (Kyrie Irving to Boston). If he’s healthy, Oladipo would be an awesome option alongside Kemba Walker like you mentioned — especially defensively. But, it also does get murky when you consider the Celtics also have Marcus Smart, Jaylen Brown and Jayson Tatum also operating on the perimeter as well. That can make things clunky with Oladipo and probably makes it less likely he ends up with Boston.

Cleveland is in a similar vein to Boston when it comes to obtaining Oladipo. Sure, adding him to this current Cavs’ squad would likely give them the jolt in star power that Andre Drummond hasn’t provided, at least so far. But, his fit becomes clunky considered the Cavs are trying to grow and nurture ball-dominant guards in Collin Sexton, Kevin Porter Jr., and Darius Garland.

Adding Oladipo to the mix only complicates that and also hamstrings the development of the Cavs’ young stable of players. He also doesn’t seem likely to re-up in Cleveland if he wants out of Indiana. So, for now, the Cavs politely decline if the Pacers come calling offering Oladipo. But, if Indiana instead was offering Turner, it would be an entirely different story.