No. 2 – P.J. Tucker
Unlike most of the names on this list, P.J. Tucker was not a youngster when the Bucks gave up on him; he was an established player in his late 30s. Tucker spent just a few months in Milwaukee in the 2020-21 season, where he was brought over in a trade with the Houston Rockets. Of course, that was the season Milwaukee won the NBA title, and Tucker certainly played a big part in the team finally getting over the hump.
Despite serving as a starter for most of the playoffs that season and helping Milwaukee reach the promised land, the Bucks shockingly let Tucker walk. It was a move that blindsided everyone, as it seemed inevitable that he would return for another go-round. Yet, he inked a deal with the rivaling Miami Heat instead. It’s unclear what exactly happened in the negotiation room, but it appears the Bucks may have tried to go cheap with Tucker on his next deal and lowballed him.
Since letting Tucker go, the Bucks have tried replacing what he brought to the table with a mix of different players. They brought in Semi Ojeleye in free agency that year, and he became unplayable in the span of a few months. They then added Wesley Matthews, who has been solid since coming back to Milwaukee, but not on the same level as Tucker. They added Jae Crowder this year, but he failed to make much of an impact and spent most of the playoffs on the bench.
Rather than trying to replace Tucker, the Bucks probably should have just coughed up the money to keep him. Since his departure, they’ve lacked some toughness and a go-to wing defender who is not afraid of the most imposing assignments. The decision to let him go will continue to be a big talking point among the fanbase for years to come.