Milwaukee Bucks: Going through the rollercoaster of emotions this offseason

The Milwaukee Bucks’ offseason offered nothing short of drama and excitement going into the start of training camp and less than a month before the start of the 2020-21 season.

In easily the most critical offseason in franchise history, it appeared as though the Milwaukee Bucks were up for tackling such a challenge.

Even before free agency had even started, the Bucks had appeared to hit a home run with the blockbuster acquisition of Jrue Holiday and what appeared to be a sign-and-trade deal for then-Sacramento Kings restricted free agent Bogdan Bogdanovic.

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In one fell swoop, the Bucks looked to have assembled their most talented five in franchise history. But as the week unfolded and new developments came pouring in going into the start of free agency, Bucks fans certainly had to hang on in what was a rollercoaster of an offseason.

And those emotions do not even include the supermax decision yet to be made by Giannis Antetokounmpo.

The prospect of landing a superior upgrade at the point guard position was all too enticing after having seen Eric Bledsoe’s playoff failures in each of the last three seasons. While the Bucks had made it known they weren’t interested in pursuing Chris Paul, they were reportedly interested in Dennis Schröder before he ultimately landed with the reigning champions, the Los Angeles Lakers.

That failed pursuit put Bucks fans on the edge of their seats as everyone was searching for who they could realistically make to land a superior ball handler and more proven performer.

It’s very possible that the Bucks acquired the best replacement available on the market for Bledsoe in Holiday, even at the exorbitant price that the Bucks parted with in what ended up being a four-team trade. And to add someone that has long been a dream target of Bucks fans truly made for a wild night.

While the Milwaukee Bucks landed Jrue Holiday, the saga of Bogdan Bogdanovic has overshadowed their offseason.

But the elation in seeing both Holiday and Bogdanovic come to Milwaukee in what was essentially a package deal seemed too good to be true. In the end, that proved to be the case.

The bewilderment and confusion that set in for myself and all Bucks fans felt, especially after the Bucks had waived Ersan Ilyasova ahead of his salary guarantee date, broke down the framework of the deal that would have sent the Serbian international to Milwaukee.

From there, the Bucks had to pivot quickly on the cusp of free agency getting underway. As they saw veteran depth pieces like Robin Lopez and Wesley Matthews go elsewhere, the Bucks looked to bring back one of their own in Pat Connaughton.

But even retaining Connaughton on what ended up being a three-year, $16 million deal became fraught with questions and plenty of head scratching in the aftermath of the news.

However, to see the Bucks piece together their depth and bench unit with the additions of D.J. Augustin, Torrey Craig, Bryn Forbes and Bobby Portis, at best, gives them the shot in the arm they need in this roster makeover. Will it be enough, especially after the dreams of Bogdanovic coming to Milwaukee go up in smoke? It remains to be seen, but the failed bid for Bogdanovic will certainly loom over the Bucks’ 2020-21 season, without question.

All of this and the biggest question hanging over this Bucks offseason remains unresolved. The Bucks are “cautiously confident” that Antetokounmpo that inks his five-year supermax extension this offseason, but whatever his decision may be, there’s no sign this rollercoaster appears to be slowing down anytime soon.