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The New Win-Now Milwaukee Bucks

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After two decades, Milwaukee seems to approach “Win Now” the right way.

NBA: Los Angeles Lakers at Phoenix Suns Mark J. Rebilas-USA TODAY Sports

The Herb Kohl-era Milwaukee Bucks brought many things to fans. These included two logo changes, several different jerseys, a run to the Eastern Conference Finals, the rally cries “Fear The Deer” and “Bucks in 6,” and a commitment to staying in Wisconsin. There was also plenty of mediocre (or poor) basketball that fans had to watch. Despite all of that, there was one issue that many Bucks fans had; during this reign, the personnel decisions never got the Bucks over the hump. With the Eric Bledsoe trade, some people see it as a win-now move and have some fears, but are those fears justified?

Past Situation

For much of the last 15 years, Milwaukee always was a team that either were pretty poor (2013-14 season) or meh (almost every season besides 2009-10 season). During those seasons of mediocrity, Milwaukee would usually sit just outside of a playoff spot, or be one of the lower seeded teams. Since the “Light it Up” 2000-2001 season, Milwaukee has not made it past the first round of the playoffs or had home court advantage.

Much of that is because the team always had good, but not great, players leading the team like Michael Redd, Andrew Bogut, and Brandon Jennings. While Redd and Bogut got hit badly with injuries that made them a shell of their former selves, the team was banking on them to get the Bucks to the next level. Unfortunately, this never happened. Redd was tabbed the star after the team infamously traded away Ray Allen, while Bogut was drafted before Chris Paul and Deron Williams. Ironically, Milwaukee would draft their superstar in the final year of the Kohl ownership in Giannis.

Mistakes Made and Opportunities Lost

Kohl had always wanted to make sure that his team made the playoffs. While that ambition was admirable, it hurt the Bucks in the long run. This situation was similar to the Philadelphia 76ers during the Andre Iguodala era. As previously mentioned, Milwaukee made a few roster moves that created the win-now narrative. The first and most-glaring error was trading team star Ray Allen for Gary Payton and Desmond Mason. While on paper that doesn’t sound like a bad trade, in reality this was a Gary Payton who was in his 13th season in the league and was going to be a free agent after the season, and was leaving the first opportunity he would get.

That trade left the Bucks without a star after the Glove rental expired, and only an “okay” player in Mason remained. This trend would continue in the 2005 trade for Jamaal Magloire while giving up Mason and a first round pick. We saw it again in 2012, trading Bogut for Monta Ellis, and again in 2013 when the Bucks traded young prospect Tobias Harris for J.J. Redick. Each of those moves were made to get the Bucks in a playoff spot, any playoff spot, but not enough to make them a contender.

The Magloire trade left the team without a draft pick and while the Hornets used that pick to draft Cedric Simmons, Milwaukee could have used that pick on someone like Rajon Rondo or Kyle Lowry. The Ellis trade really hurt, because instead of trading for some guy who can shoot but had ankle problems named Stephen Curry, Milwaukee traded for Ellis, which some people in sports media ripped the Warriors for doing in the first place.

Fast forward five years and that move looks worse and worse. But with Ellis, Milwaukee was still in the playoff hunt and wanted to get someone to help them now, not later, which meant that a young piece had to be traded. In hindsight, it was tough to see Steph be as great as he’s been the last few years, or Harris who in 2012 didn’t have a role, while now he would be a great fit on a roster. These moves always put a low ceiling on the Bucks as a team that could make the playoffs, but never really made you believe a strong run was possible.

Key Differences

While the trade is a “win now” move, some fans view parting with a first round pick more risky than ever before. This move for Bledsoe is different. Before, Milwaukee never had a true genuine superstar; they haven’t had someone who can single-handedly win you a game just by being better than everyone else on the court. Now they do and when you hit that stage, you need to get pieces around him. The talent needs to be at a level so that your superstar can see that the front office is trying to help them as much as they can.

Khris Middleton was a start (and a bargain), and a healthy Jabari Parker might have helped (and might still. Add the revelation of Malcolm Brogdon and the steady shooting of Tony Snell, and you can see that Milwaukee has begun collecting the pieces. Bledsoe is a talented guard that was easily attainable after he said that he wanted out. While not a superstar, he is a player that will help any roster and at a position Milwaukee was lacking quality. The timing was perfect.

Due to the unique protections, the departing first round pick will be gone at some point whether it’s next season or 2021. But with the Eastern Conference crown more vulnerable than ever before, and a Top-5 caliber player on the roster for the next four years, the time to make moves to win is now.

Same Results?

Ultimately, we won’t know the repercussions until years down the road. Milwaukee can turn this early season slump around and make a run as contenders in the Eastern Conference, and maybe even make other roster moves to move towards the ultimate goal of a Finals berth. Milwaukee could also crash because of this move, and it could set the franchise back for years (especially if the unthinkable regarding Giannis playing in a city not ending in “-ilwaukee” happens). This trade is only a factor of the win-now window, as other factors like cap management, internal roster growth, and coaching have just as much of an influence. As a Bucks fan for the last 20 years, this win-now move is justified compared to the moves during the Kohl era. Back then those moves were made to be good enough, now these moves are an attempt to be great.