In the spring of 2013, the final buzzer sounded for the Milwaukee Bucks in Game 4 of the 1st round of the NBA Playoffs against the Miami Heat.
The Bucks returned to the playoffs in hopes of breaking a drought of four-straight first-round exits.
Times were tough in Milwaukee. Seemingly nobody wanted to be there. For the diehards, there was this fake excitement of just trying to be positive that the Bucks were able to pull off a trade for JJ Redick…and pairing him up with Brandon Jennings and Monta Ellis???
As the Bucks season came to a sweeping halt against a screaming-hot Heat team who went on to win the NBA championship, fans could almost sense they’d be in for a very long string of bad basketball. A trade that would change Milwaukee Bucks culture would occur in the summer, however.
The Trade of the Brandons
On July 31st, 2013, the Bucks traded Brandon Jennings in a sign-and-trade deal to the Detroit Pistons for Brandon Knight, Khris Middleton and Bucks Legend Viacheslav Kravtsov. Jokes aside, Middleton coming to the Bucks was, for the lack of a better term, the throw-in piece of the trade.
Knight was supposedly the key to this trade, and had his moments, both good and bad.
The Bucks, however, found themselves a diamond in the rough with Middleton during an otherwise horrific time in the franchise’s history. Luckily, they have never had to look back.
In Middleton’s first year with the Bucks he saw all 82 games, started 64, averaged 12.1 points over 30.0 minutes per game on 44% shooting. Though that isn’t an incredible stat line, Khris would start to make a significant difference as time would progress, even finishing 12th place for the Most Improved Player Award the following season.
Middleton Emerges as No. 2(2)
As the Brandon Knight and painful Michael Carter-Williams experiences came to a merciful end, Middleton was no doubt becoming the number two option. Although he would injure his hamstring in the 2016 preseason — leaving him out for nearly two-thirds of the year —Bucks fans would soon have to live by a phrase, “Khris Middleton is Good.”

In the 2017-18 season, Middleton started 82 games, averaging 20.1 points (47% FG, 36% 3PT, 88% FT), 5.2 rebounds, 4.0 assists and 1.5 steals across 36.4 minutes per game. He finished right behind Giannis Antetokounmpo in points scored at No. 2, was selected to his first All-Star Game in the following year, scored a career high thereafter in the 2019-2020 season, and ever so sweetly, hoist the Larry O’Brien in the 2020-2021 season.
While this article has highlighted all of Middleton’s success, it doesn’t really match the title. Khris is set to make $31.7 million this year and has a player option the following. The thought of Middleton not being on this team is something some Bucks fans wouldn’t mind and others be heartbroken over.
Injury History Cannot Be Ignored
Khris just turned 33 years old, and he had surgery on both ankles this offseason. After the 2022-2023 season concluded, he also had surgery on his knee. That’s not all, as we of course remember the injury he suffered in the playoffs against the Bulls in 2022 where he sprained his MCL, ending the Bucks’ real chances of repeating.
Barring any sort of ridiculous trade, Middleton is in the driver’s seat for the remainder of his contract with the Bucks. Some may think it’s asinine to suggest that this would be his last season in basketball.
But he may have to take stock in how many injuries are piling up and how much of a physical toll that it is taking on his body.
During his tenure with the Bucks, Middleton has never seemed to have the quickness that a guard has. As seasons roll by, just by body language alone, even a casual could pick out that he can sometimes be as slow as Kareem Abdul-Jabbar was when he was running up and down the court.
It would be nice to see a recovered Middleton in the best shape of his life at the start of this season. Unfortunately, that has continued to be the hope too many seasons in a row.
This Season Will Determine the Rest
Sure, 33 seems like an early age to retire from basketball and it appears Middleton has gas left in the tank for this upcoming season, yet once again the body language he exudes can sometimes look otherwise.
With Giannis’ window of opportunity slowly closing as each day passes, Middleton will have more help from a hungry Damian Lillard and other offseason additions.
As we remember, Jrue Holiday floating the idea of retirement, fans should not be shocked if those same words are mulled by Khris Middleton at seasons end.
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