The 2025 Cleveland Cavaliers have a winning record this year, but have looked inconsistent. They have talent, but they are stuck with their roster at the moment due to how much money is owed to their best players. That has hamstrung them in trying to improve their roster and has not allowed for roster flexibility. They might have to make some moves at the trade deadline to allow for flexibility, and that starts with Darius Garland, who has been dealing with injuries.
On the latest episode of “The Bill Simmons Podcast,” Bill Simmons floated the idea of the Cavaliers trading Darius Garland to Khris Middleton for his contract and some picks. That is because the Cavaliers are stuck on the second apron, which hurts their roster flexibility overall, and a move like this could help them instantly.
Simmons said, “They could trade Garland but the one for one rules that they’re handicapped with, they’re really screwed. Like here’s a trade they could do. They could trade Garland to Washington for Khris Middleton’s contract and picks. Which Washington might think about but that would only save them $6.2 million. They’d still be way under the apron.”
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Darius Garland has struggled this season in comparison to his past seasons in Cleveland. He can't stay healthy, playing in only 12 of the Cavaliers' 28 games. The injuries are partly to blame, but Garland's scoring has also taken a dip, with him averaging 15.4 points per game after averaging 20.6 points per game last season.
The Wizards are in the depths of a rebuild, and if they made a trade like this, it would give them a player closer to their timeline than Khris Middleton, who is older. Garland is 25, while Middleton is 34 and recently picked up his option in the final year of his contract this season.
That trade could work well for everyone because Garland has a lot of potential and could get even better where he is not the second option and instead has his own team, especially in the backcourt. Then, for the Cavaliers, they get extra help on the wing and draft capital they desperately need to keep a flexible roster.