The Milwaukee Bucks are known for being one of the most commercially active teams in the NBA.

Whether the move goes through or not, general manager Jon Horst has never shied away from making a splash if he feels a move could help the team. In most cases, the moves made by the former Executive of the Year were easy to justify when they were made. However, for many of them, for one reason or another, things never work out the way fans had hoped.

Let’s analyze three different trades from recent memory that should have worked out better for Horst and the Milwaukee Bucks.

Fresh off a title win in 2021, the Milwaukee Bucks bolstered their backline by acquiring point guard Grayson Allen from the Memphis Grizzlies. Considering the Bucks parted ways with Sam Merrill, the 60th overall pick in the 2023 NBA draft who barely played last season, and two second-round picks, this was seen as a clear win for the Milwaukee Bucks in their quest to repeat.

At the time of the trade, Allen was coming off a career season in Memphis, averaging double-digit points and ranking among the league’s top shooters. He would fit in nicely with the Bucks’ stars while providing insurance at the second-down guard position as Donte DiVincenzo recovers from surgery. This had the potential to be one of Horst’s best trades, given the price and team needs.

Allen had his moments, even putting together the best regular season of his career in 2021-22. Yet the moment that will define his time in a Bucks uniform is the 2022 playoff series against Boston. After catching fire in the previous series, Allen’s production fell off a cliff against the Celtics, averaging five points while shooting 20.8 percent from three-point range and being constantly targeted on defense.

The point guard had a nice season the following season, shooting the long ball well while increasing his production as a facilitator. His play wasn’t as bad in the 2023 NBA playoffs as it was in this series against the Boston Celtics, but he still didn’t set the bar high enough against the Miami Heat, especially with the team missing Giannis Antetokounmpo.

After two years, Allen’s stint with the 414 came to an end after he was sent to Phoenix to the three-man squad. Damian Lillard deal. While the initial Allen trade certainly isn’t a stain on Jon Horst’s legacy or anything close to it, it’s a deal that should have worked out much better than it ultimately did over the course of those two seasons the guard was with the franchise.

If Allen plays up to par in this series against Boston, there’s a good chance another banner will be hanging on the Fiserv Forum right now.

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