Cleveland jumped at the chance to land Andre Drummond in a deadline trade for next to nothing. The goal was for the two sides was to play out the rest of the season and see if there was a fit, except that turned out to be only eight games due to the pandemic.
This summer, Drummond has all but said he would pick up his $28.8 million option and remain with the Cavaliers. While there was some early optimism about an extension, that has faded as the sides are far apart, reports Chris Fedor of the Cleveland Plain Dealer in a recent Q&A.

The sides have been far apart in those preliminary discussions, sources say. The Cavs recognize Drummond’s talent but they are also honest about his flaws, especially in this pace-and-space era, where bigs like him are easy to attain… Drummond, meanwhile, wants to be compensated for bypassing a chance at 2021 free agency, when many teams will have significant cap space. Given the differing, current monetary views, an extension seems unlikely.
Does that open the door to an Andre Drummond trade? Maybe, there have been rumors about a Drummond trade before. He provides some real value to the right team as a strong pick setter and rim runner who can block shots and clog the paint defensively, plus he’s a beast on the glass. Drummond averaged 17.7 points and 15.2 rebounds a game last season.

Fedor’s sources suggest a trade is more likely to be a deadline deal than an offseason one.
Multiple league sources believe the Cavs’ best chance for a trade would be at the deadline, sending him to a contender looking for an additional piece with no financial commitment beyond the 2020-21 season.

With Drummond’s hefty contract, it’s next to impossible to imagine a trade to a contender this offseason. None of those teams is going to give up good players/picks to take on that much salary for a player whose skill set others can replicate (for example, there is zero chance the Clippers would give up Ivica Zubac and more to land Drummond, it doesn’t make them better). At the deadline, maybe, depending on how things play out for teams and Drummond. Even then, it’s a maybe.
An Andre Drummond trade could happen, but it’s going to require patience from fans and the front office.