The Cleveland Cavaliers and the Milwaukee Bucks are ships passing in the night.
After years of dominating the Eastern Conference behind the two-way play of Giannis Antetokounmpo and his wingman Khris Middleton, the Bucks are falling apart. Middleton has yet to play a game, the rest of the rotation looks old and slow, and Milwaukee is at the very bottom of the East standings at 1-6.
The Cleveland Cavaliers, however, are soaring. They have ascended into the space at the top of the conference that the Bucks have vacated, pinning to their own chest the nametag of "biggest threat to the Boston Celtics."
To truly push for an NBA Finals berth and a second championship for the city of Cleveland, the Cavaliers may need a little more oomph on offense, someone who can take and make shots in a gummed-up halfcourt setting. Donovan Mitchell can do that, and perhaps Darius Garland to an extent, but the Cavs would benefit from someone with size who can also create a shot.
If the Bucks self-destruct, which they seem very close to doing, the Cavaliers will be among those banging on the door and demanding both answers and good deals. This trade would be the boldest one, the invitation both teams might have needed but not wanted to initiate themselves.
Laying out the trade details
Here are the details of a 3-team trade:
For the Bucks, this deal would be in large part about digging themselves out of salary cap prison as they pivot toward a rebuild. It's not unthinkable that they make this deal for the here-and-now, but most likely they pull this lever if things are all over for the Bucks as a contender.
Instead of being committed to Khris Middleton's $31.67 million salary for next season (he has a player option he will almost certainly pick up) the Bucks get a pair of expiring deals in Caris LeVert and Ty Jerome, and Georges Niang's relatively minor contract for one further season. Each of those players would have some value of their own to flip on to another team, particularly LeVert. The 2031 first-round pick is far enough out that the Cavs' future is uncertain and could end up in the lottery.
It's not an overwhelming return for a former All-Star like Middleton, but given his age and continual injury history it's fair value, and because of how much Middleton makes there may not be a long list of suitors at the trade deadline.
Should the Cavaliers make this deal?
The Cleveland Cavaliers committed to this core of players again this summer, signing Donovan Mitchell, Evan Mobley and Jarrett Allen to extensions. That belief has paid off thus far with an 8-0 start, but it also doesn't yet speak to whether they can contend at the highest levels in the playoffs.
It's hard to find a player more proven in playoff settings than Khris Middleton, and this deal allows the Cavs to add a top-flight scoring option without touching their core of players - not the four stars, not Max Strus or Dean Wade, and not their first-round pick Jaylon Tyson.
Caris LeVert has become an important piece for the Cavaliers, but he is replaceable, especially with Middleton stepping in as an on-ball scorer and secondary playmaker. Georges Niang will be on the fringes of the rotation when Strus returns, while Ty Jerome may not be in the playoff rotation and has a ready-made backup in Craig Porter Jr. These are all good players, but they are not irreplaceable.
Using their 2031 first-round pick fires off their single best draft asset, but it's unclear who would be a better target than Middleton. He can either start at the 3 or even come off the bench as a super sub, playing limited minutes over the course of the regular season to be ready for the playoffs.
This is a trade that makes a lot of sense for both sides, and if the Cavaliers get the opportunity to make this trade they should strongly consider placing the call.