Milwaukee Bucks: Did they really have one of the worst offseasons?

A recent ESPN survey that polled eight anonymous scouts and executives weighed in on the Milwaukee Bucks’ clumsy offseason heading into the 2020-21 year.

With nearly a week to the start of their 2020-21 campaign, the Milwaukee Bucks are ramping up action into a critical season.

The fact that it comes after what was a whirlwind offseason in general, but one that was especially so for Milwaukee as they overhauled their roster down to their foundation. But as all Bucks fans would readily admit, the organization’s many moves this offseason didn’t come without some significant hitches along the way.

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To that point, in a recent survey held by ESPN’s Tim Bontemps that polled the opinions of eight anonymous scouts and executives, the Bucks stood out in one particular category for all of the wrong reasons.

The Bucks were singled out as one of the teams that were voted to have the worst offseason this year, along with with the Detroit Pistons and the Houston Rockets. The clumsy pivot they had to make after the failed bid for Bogdan Bogdanovic even led to one executive saying the following:

"“Milwaukee was kind of left holding the bag,” an Eastern Conference executive said. “A lot of it seemed to be just because they were disappointed they didn’t execute their plan, or they didn’t have a better plan. It just seemed like after the [Bogdanovic] deal they were scrambling.”"

That tough assessment undoubtedly hits home with Bucks fans who wished to see Bogdanovic wearing green and cream only for it to go up in smoke and have an ongoing tampering investigation lurk in the background. And there was the whole Pat Connaughton deal that originally wasn’t legal under the CBA, all of which led to him garnering a bigger deal at three years and $16 million.

For as ungraceful as some their offseason dealings were, the Milwaukee Bucks’ offseason will be defined by Giannis Antetokounmpo’s decision on his supermax extension.

Ultimately, though, the biggest of the Bucks’ offseason still remains unanswered.

(UPDATE: Giannis announced himself Tuesday afternoon that he has signed his five year, $228 million supermax extension, which includes a opt-out clause in 2025).

The deadline for when Bucks superstar Giannis Antetokounmpo is able to sign his supermax extension offer is ticking down as he has until next Monday, the day before the NBA season starts, to sign said offer. As of this writing, the two-time MVP has kept his cards close to the vest regarding his decision, while the speculation surrounding his decision is nearly at a fever pitch.

But there’s no question that the team’s front office felt the urgency to put forth a better, more playoff adaptable roster in light of their last two playoff downfalls that exposed their outstanding flaws. That’s where their blockbuster deal for Jrue Holiday, that included three first rounders and a pair of pick swaps, comes into the picture and the Bucks are hoping that will be enough to turnaround their playoff struggles of the last two seasons.

Holiday isn’t immune to questions surrounding his own future himself, either. With a $26.2 million player option for next season, Holiday’s future is as much of a question as Antetokounmpo’s and like the two-time MVP, Holiday is extension-eligible starting in February.

Do the Bucks make a significant move to bring in Holiday, especially at the price they did, without having some confidence that the veteran guard would be interested in re-upping with the Bucks about an extension? That’s the next dilemma they face and it all goes to the fact that they’re doubling down on the present with Antetokounmpo’s future all but a given beyond this season.

With all of that in mind, the high-risk, high-reward nature of the Bucks’ offseason and the anxiety surrounding the two-time MVP’s decision could all be alleviated by him signing some sort of extension before the season starts. Would that alone make up for what was far from a shrewdly executed offseason for the Bucks?

All Bucks fans would agree that it wouldn’t, but having more time and some assurance that Antetokounmpo is tied to Milwaukee in some fashion beyond this year would simply come as a relief. While acknowledging that more work has to be done to capitalize on their open championship window.

Be on the look out for when we hand out our final grade on the Bucks’ offseason in the next couple of days and break down the various ways they got better and where they potentially got worse.