The Cleveland Cavaliers are hovering in that frustrating middle ground - not quite bad, but not nearly as good as many expected heading into the season. Nearly 50 games in, they’ve been the definition of inconsistent: a couple of steps forward, then a stumble. That kind of rhythm doesn’t cut it in a crowded Eastern Conference, and with the trade deadline looming on February 5, a roster shake-up feels more like a matter of when than if.
One potential move that makes a lot of basketball sense? A deal with the Milwaukee Bucks centered around Bobby Portis and De’Andre Hunter. On paper, it’s a clean swap - each team addressing a glaring need, no draft picks required, and both players fitting more naturally into their prospective new homes.
Let’s unpack it.
Why this works for Cleveland
The Cavaliers have been searching for stability at the power forward spot all season. Portis would give them exactly that - a stretch four who brings toughness, playoff experience, and, oh yeah, he’s currently leading the NBA in three-point percentage. That’s not just a bonus - it’s a game-changer for a Cavs offense that can bog down without consistent floor spacing.
Portis isn’t just a shooter, either. He’s a grinder on the boards, a vocal presence in the locker room, and someone who doesn’t shy away from big moments. Adding him would give Cleveland a true power forward, something they’ve been missing, while allowing Jaylon Tyson to fully slide into the small forward role - a move that feels overdue given how well the rookie has played compared to Hunter this season.
Tyson’s emergence has made Hunter somewhat expendable, and this trade would be a clear signal that the Cavs are ready to lean into their younger core while still competing now.
Why this works for Milwaukee
The Bucks, meanwhile, are in a different kind of desperation mode. Their depth has been exposed, particularly on the wing, and the supporting cast around their stars isn’t holding up. The rotation has too many question marks and not enough answers - especially at the wing, where the current group (Gary Harris, Gary Trent Jr., Amir Coffey) just isn’t cutting it.
Hunter would immediately become a key piece in Milwaukee’s rotation. He’s a capable defender with size, he can knock down open shots, and he brings a level of polish that the Bucks are sorely lacking on the perimeter. He’s not a star, but he’s a real NBA wing - and right now, that’s exactly what Milwaukee needs.
The Bucks may not have the draft capital to chase bigger names, but Hunter represents a realistic, attainable upgrade without mortgaging the future. It’s the kind of smart, no-frills move that could stabilize things before the situation escalates - because when your franchise player is watching the team flounder, the clock is always ticking.
The financials check out, too
To make the money work, the Bucks would likely send Gary Harris along with Portis - Harris functioning as a salary match more than anything else. It’s not a flashy deal, but it’s clean, it’s logical, and it helps both teams address immediate needs without overcomplicating things.
A rare win-win scenario
Trades between division rivals are rare - and understandably so. But sometimes, the fit is just too good to ignore.
The Cavs need frontcourt help and spacing. The Bucks need wing depth and defensive versatility.
This deal checks both boxes.
It’s not a blockbuster in name, but it could have meaningful ripple effects for two teams trying to stay in the Eastern Conference hunt. For Cleveland, it’s about finding the right pieces around Donovan Mitchell and Darius Garland. For Milwaukee, it’s about keeping the window open while Giannis Antetokounmpo is still in his prime.
Both teams are in win-now mode. This trade would help them do exactly that.