Some gambles aren’t worth taking. For the Milwaukee Bucks, keeping Khris Middleton beyond the trade deadline might be the one bet they can’t afford to lose.

The Heat, Pistons, Wizards, and Raptors are all listed as teams that could be a good fit for Middleton. All of those teams need a veteran guy who can help a younger team thrive, except maybe Miami.

The Milwaukee Bucks have some difficult decisions to make surrounding Khris Middleton as they balance sentiment and pragmatism.

The Bucks have been active this trade season, sources said, with Khris Middleton, Bobby Portis and Pat Connaughton all expected to be available in potential moves to bring back an impact player.

Here is all the latest news you need to know about the Milwaukee Bucks, including why their game against the New Orleans Pelicans was postponed.

Bucks star Khris Middleton is an NBA champion that has shined on the biggest of basketball stages. Now, on this stage, inside the Big Brothers Big Sisters of Metro Milwaukee's MentorZone, he's interested in winning over a new crowd.

Milwaukee Bucks remain interested in Jimmy Butler and are reportedly willing to trade Khris Middleton to acquire him. “Amid rumors surrounding Butler and the Bucks possibly emerging as the main dark horse to land him in a trade deadline blockbuster, the one thing that everyone… pic.twitter.com/supaGdjPKV

Bucks star Khris Middleton is helping out at the Big Brothers Big Sisters of Metro Milwaukee's MentorZone Middleton grew up with mentors, and now he's paying it forward as a long-time advocate for ...

Because the Bucks have crossed the NBA’s second tax apron, players like Connaughton or Portis would have to be traded away to make a deal like this happen. Milwaukee can’t aggregate players in a trade unless that trade gets them under the tax apron.

The Miami Heat could acquire Milwaukee Bucks' wing Khris Middleton due to the disgruntled state of their own star.

Giannis Antetokounmpo can't make free throws again and Khris Middleton is thriving off the bench, complicating the Bucks trade deadline plans.