Milwaukee Bucks: All eyes turn to ownership going into pivotal offseason

MILWAUKEE, WISCONSIN - MAY 23: (Photo by Jonathan Daniel/Getty Images)
MILWAUKEE, WISCONSIN - MAY 23: (Photo by Jonathan Daniel/Getty Images) /
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As the Milwaukee Bucks come to grips with a pivotal offseason, our attention turns to the team’s ownership who will influence the team’s next course of action.

Whether they want to admit so or not, the Milwaukee Bucks are nearing on a crossroads of sorts.

For the second straight regular season, the Bucks finished with the league’s best record and captured the one-seed in the East. Not only that, but they will soon have the back-to-back MVP in Giannis Antetokounmpo, they have a two-time All-Star in Khris Middleton and both Eric Bledsoe and Brook Lopez have officially landed on the NBA’s All-Defensive Second Team. All while two-time NBA Coach of the Year Mike Budenholzer has pulled the strings from the sidelines.

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And yet, for the second straight season, the Bucks have seen their run go up in flames in the playoffs far earlier than anyone expected, this year being more fiery after losing to the Miami Heat in five games in the Eastern Conference Semi-finals.

Running into in an incredibly bad matchup in the Heat aside, the Bucks now have to come to grips with an early playoff exit and an offseason that’s ripe with uncertainty ahead of Antetokounmpo’s free agency. And it starts from the top on down.

As we’ve seen many outlets write in light of the Bucks’ failure to reach their ultimate goal of winning an NBA title and rightfully so, Milwaukee’s ownership, led by the trio of Jamie Dinan, Wes Edens and Marc Lasry, aren’t above blame for the team’s ultimate failures.

That all revolves around their collective decision to avoid going into the luxury tax for this season, which spurred the sign-and-trade deal with the Indiana Pacers for Malcolm Brogdon. As they told it during their press conference before the start of the season, it wasn’t a matter of avoiding the luxury tax altogether. They knew it would be coming, but chose to avoid doing so this year.

It’s clearly their imperative to make such a decision and before the regular season was suspended, it looked as if the team’s quest to win a title would be validated without the need to rehash the Brogdon/luxury tax discussion. Nonetheless, it simmered throughout the Bucks’ run into the playoffs and boiled over when things blew up in the Bucks’ face, just as other recent big picture decisions have re-entered the discourse as well.

By pushing the ball down the road in regard to entering the tax, it has directly informed the very tough spot the Milwaukee Bucks are in and in what direction they can possibly go next this offseason.

Unlike the last couple of years, there are no obvious solutions or fixes that have to be made.

It’s not like fixing a mess of a coaching situation during the Jason Kidd days, all of which led them to Budenholzer. Their overwhelming success during the 2018-19 season and run to the Eastern Conference Finals made retaining their core players entering free agency incredibly pertinent to their longevity in this window. Well, until the cost became too much to bring ALL of those core players back again.

Now, the Bucks enter an offseason where they have little flexibility or mechanisms to shore up or even upgrade a roster that will need to be addressed. Despite sporting the many playoff shortcomings that have followed him throughout his coaching career, Budenholzer’s job in Milwaukee is reportedly safe for the time being.

There are already rumors of the Bucks exploring a move for sure-to-be Hall of Famer Chris Paul, but that requires working around a lot of potential pitfalls and also footing the bill on Paul’s rather extravagant salary, which will be a combined $85 million over the next two seasons.

Ultimately, to make such a move for Paul or explore any serious upgrades, all in the name of winning a title and appeasing Antetokounmpo, puts the onus on the Bucks’ ownership and their willingness to spend. Again, they will assuredly spend and the Bucks will be in the tax, even with all of the uncertainty surrounding the cap at this time.

But how much they’re willing to spend is the bigger issue as the Bucks have reached their fork in the road. And the harsh financial realities, in light of the coronavirus pandemic, that will affect a 2020-21 season that is far from concrete at this stage has made that question all the more pressing.

At their own doing, the Bucks have backed themselves into this corner, where no solution or quick fix is both easily identifiable and can be put into action. Now in a year where Antetokounmpo holds all the cards and can state his intentions to stay long-term in Milwaukee whether or not he signs his supermax extension, the Bucks face their biggest test in maintaining their current title window this offseason.

Next. 4 lessons learned in face of Bucks' disappointing playoff exit. dark

For the second straight year, following the money will determine whether Bucks ownership’s talk of winning an NBA championship will prove cheap or not.