The 2021-22 NBA season will always be categorized as a massive "what if" for the Milwaukee Bucks.
With Giannis Antetokounmpo dominating, Khris Middleton putting up over 20 points per contest and Jrue Holiday playing elite two-way basketball, the Bucks seemed well-positioned to defend their title. However, in their first-round playoff series against the Chicago Bulls, Middleton slipped on a wet spot, suffering a sprained MCL that sidelined him for the remainder of the NBA Playoffs.
Even without Khris Middleton healthy, Milwaukee pushed the eventual Eastern Conference Champion Boston Celtics to seven games in the second round. They lost in crushing fashion in Game 7, forever making Middleton's injury one of the prominent "what ifs" in franchise history. Would there be another banner hanging in Fiserv Forum right now if Middleton didn't slip? It's entirely possible.
There's no arguing that Middleton is the biggest "what if" from that season, but there is another, to a much lesser degree, and that's DeAndre' Bembry. While Bembry wouldn't have guaranteed another championship, he certainly wouldn't have hurt their odds, given how everything played out.
DeAndre' Bembry checked off the boxes for the Milwaukee Bucks
After being let go by the Brooklyn Nets mid-season, DeAndre' Bembry was swiftly picked up by the Milwaukee Bucks. Bembry previously played under Bucks then head coach Mike Budenholzer, so he was reuniting with a familiar face.
Early in his tenure with the Bucks, Bembry showed that he could help by serving as a spark off of the bench with his defense, cutting and attacking in transition. It looked like he was destined to see more minutes down the stretch and into the NBA Playoffs.
Unfortunately, eight games into his tenure with the Milwaukee Bucks, Bembry suffered a devastating knee injury, having torn his ACL and MCL. Obviously, he was sidelined for the remainder of the season and has still not played in the NBA since that day.
It was brutal for the Milwaukee Bucks at the time, but it only got more amplified in the NBA Playoffs.
How Bembry could have helped the Bucks vs. Boston
With Khris Middleton down, the Milwaukee Bucks were short a wing. With both Pat Connaughton and Wesley Matthews already exceeding 29 minutes per contest, someone else needed to be relied on at the wing spot to try and fill Middleton's shoes, and that player was Grayson Allen.
Unfortunately for Milwaukee, rather than stepping up like he did against the Bulls in the series before, Allen was horrendous against Boston. In over 26 minutes per game, he averaged just five points while shooting 31 percent from the floor and a vile 20.8 percent from deep. He was nothing short of awful.
One could argue that his defense was even worse. The Celtics targeted Allen as if he was a wounded animal. The primary culprit was Jaylen Brown, who shot a red-hot 11-of-15 (73.3 percent) with Allen as his primary defender, per NBA.com/stats. Jayson Tatum was 6-of-13 (46.2 percent), and Marcus Smart was 4-of-9 (44.4 percent).
Allen had a horrific series, but with Middleton injured and the team already pushing their other two main wings to the brink in terms of output, they had nowhere else to turn. Had Bembry been healthy, perhaps things could have been better for the Milwaukee Bucks.
To be clear, Bembry is not swinging a series against the Boston Celtics. However, given how badly Allen was playing on both sides of the ball, it certainly would have been nice to throw him out there instead. He could have held his own better against players like Tatum and Brown, at least providing some resistance against them on the defensive end.
Would Bembry have made a difference in the end? The world will never know, but it's certainly one of the more underrated "what ifs" the Milwaukee Bucks have endured over the past few years.
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