No. 1 – Khris Middleton, Milwaukee Bucks

While they failed to reach the Eastern Conference Finals last season, losing 4-1 to the Miami Heat in the Eastern Conference Semifinals, the Bucks did everything they could to turn the roster around this offseason to convince Giannis to stay.

It ultimately worked as Antetokounmpo and the Bucks reached an agreement on a five-year, $228 million super-max contract extension that will guarantee Giannis in a Bucks uniform through the 2024-25 season, with a player option of $51 million for the 2025-26 season that will be hard to turn down on Giannis’ end. They made their superstar the highest paid player in NBA history and are all-in on winning numerous championships with him.

Now, with Giannis, Khris Middleton and Jrue Holiday, the Bucks have “championship-or-bust” on their minds and look like one of the best teams in the NBA. They are currently 9-5 and are the best offensive team in the league, averaging about 120.4 points per game, and the 2nd best three-point shooting team, shooting 40.3% from deep. 

The Bucks are undoubtedly going to be one of the Top-3 seeds in the Eastern Conference come playoff time and have a very strong chance to make it to their first NBA Finals since 1974 when they were led by Kareem Abdul-Jabbar, but if they come up short once again, Khris Middleton could very well end up being the guy that takes all the blame along with head coach Mike Budenholzer. 

Regardless if the Bucks finish with the best record in the league once again, if they lose before the NBA Finals, expect to see Coach “Budz” fired and seeing as he has been on the roster with Giannis for years now, Khris Middleton could also be on the move. 

Any trade involving Khris Middleton would not happen until next offseason at the earliest, but it is definitely not crazy to think he could end up starting the 2021-22 NBA season in a new uniform. He has been an All-Star for two consecutive years now and with him putting up better numbers than in those years statistically, it is safe to assume Middleton will be an All_Star once again this season. 

Khris Middleton’s value is going to be at an all-time high, meaning the Bucks could not only get some of the draft picks they do not have back, but they could also free up cap space to bring in another superstar talent to pair with Giannis Antetokounmpo. 

Every move this organization makes over the next few seasons will revolve around Giannis Antetokounmpo and setting not just him up for success, but this entire Bucks organization. With Giannis leading them, they have a legit shot to win the title every single season, but he will need some help along the way. That’s where a shake-up involving a Khris Middleton trade could help.