The NBA's midseason marketplace might deliver the homecoming Milwaukee fans never saw coming (but probably shouldn't want). Because as things currently stand, Washington's trade strategy could put Khris Middleton back in a Bucks uniform by February, creating the kind of emotional decision that championship teams must resist.
Per Andrew Schlecht and Alex Speers of The Athletic, Washington's early season goal is crystal clear: showcase Middleton and CJ McCollum in hopes of flipping their expiring contracts for some value before the deadline. There's also a chance he hits the buyout market later in the year, where the one-year anniversary of Milwaukee trading him could pass.
Loyalty runs deep in this league; Damian Lillard, for example, recently signed back with the franchise that took a chance on him after just two seasons with Milwaukee. So it isn't impossible for Middleton to find his way back to Wisconsin after a short break in the capital city.
A Khris Middleton return to Milwaukee suddenly isn't impossible
Even this writer, whose favorite basketball player remains Khris Middleton, knows the sentimental appeal is undeniable.
Middleton spent the best years of his career as an indispensable part of the roster that delivered the franchise's first championship in 50 years. His clutch shots, playoff heroics, and chemistry with Giannis Antetokounmpo created memories that still define Bucks culture to this day. So it absolutely goes without saying that the storybook ending of a midseason reunion would generate the kind of emotional energy that playoff runs are built on.
But vibes and sentiment don't win championships. Production does, and Middleton's recent track record has long cast doubt on his ability to stay on the court at this juncture in his career. That he played just 37 games last season should be reason enough to be wary about a reunion during the twilight of Antetokounmpo's prime years.
Obviously, the age factor compounds these concerns. Middleton is entering the phase of his career where consistent health becomes increasingly unlikely, and he'll be 34 by the time the trade deadline comes around. As we've learned the past few years, Milwaukee's championship window doesn't have time for load management or extended injury recoveries.
Washington's showcase strategy also creates leverage issues for Milwaukee. The Wizards know the emotional connection runs deep, potentially inflating Middleton's trade value beyond his current basketball worth. Other teams might view him as a rental piece, but Milwaukee would be trading for both a player and a nostalgic narrative.
Yet because of the long history between Middleton and the franchise, there's always going to be an argument for the reunion that has nothing to do with bask. For one, he understands Milwaukee's system and culture in ways that new acquisitions simply cannot. The intangibles of his leadership and playoff experience (not to mention his still-elite shotmaking) could prove invaluable during the postseason.
The reality is that Washington will more than likely dangle Middleton as the perfect midseason addition for contenders seeking veteran leadership and clutch experience. And sometimes the most difficult choices involve saying no to the players you love most.