The Cleveland Cavaliers pulled off a last-minute trade at the deadline back in February that landed them All-Star center Andre Drummond from the Detroit Pistons for John Henson, Brandon Knight and a future second-round pick. It allowed Detroit to hit the reset button and enter a rebuild of sorts, and it gave the Cavaliers a defensive center who could get boards and block shots.
The remainder of the 2019-20 season was supposed to serve as an opportunity for both sides to feel each other out to see if Drummond could envision Cleveland as a long-term home for him and visa versa, but the COVID-19 pandemic halted those plans, limiting Drummond to just eight games in a Cavs uniform. Drummond has a $28.8 million player option that he's expected to pick up this offseason, and while it was earlier reported that the two sides were discussing a contract extension, those talks have reportedly fizzled out, per the Cleveland Plain Dealer's Chris Fedor.
"At one point, there was mutual interest in an extension. However, 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. They don't want to commit to an unfriendly deal that could limit future moves, not after an eight-game sample size. 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."
If Drummond picks up his player option this offseason, and the sides don't come to an agreement on an extension, that could make him a trade candidate going into next season as he'll be playing on an expiring contract. With this talent, he can surely be beneficial to a number of contending teams, which is reportedly what Cleveland is thinking, per Fedor:
"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. That gives rival executives a chance to evaluate where they stand financially and competitively.
If extension talks don't reignite between Drummond and the Cavs, and the goal is to get something of value before he leaves in free agency, the Cavs' best option may be taking a better-fitting player with multiple years of salary. "
While Drummond is still just 26 years old, he's been in the league for nine seasons, and he's only seen the postseason twice, both times getting bounced in the first round. He averaged a career-high 17.7 points between Detroit and Cleveland this season, while corralling 11 boards and almost two steals a game. He still has plenty left to offer a quality team, so it just wouldn't make sense for him to stick around on a Cavaliers team that isn't expected to reach the postseason any time soon.
The Cavs have some promising young pieces but are still in the process of figuring out what they can become. Collin Sexton, for instance, averaged 20.8 points a game in his second year in the league. But is he Cleveland's franchise cornerstone, or will they find that in a depleted 2020 draft class where the Cavaliers are selecting fifth? Cleveland still has Kevin Love, although who knows how much longer he'll be there as it was reported last December that he wanted to be traded to Portland, his hometown.
If the Cavaliers can get another team to offer up a good enough package for Drummond, it would be a win-win for them, especially after giving up next to nothing to acquire him.