The potential ripple effects of this offseason and 2021

As the biggest question pertaining to this Milwaukee Bucks offseason remains unanswered, they face significant questions beyond the 2020-21 season.

The Milwaukee Bucks find themselves between a rock and a hard place with two weeks to the start of the 2020-21 season.

As they prepare for the upcoming campaign, Bucks superstar Giannis Antetokounmpo has yet to make his decision known whether he’s signing his supermax extension or not. On top of that, the Bucks prized acquisition of the offseason, Jrue Holiday, holds a $26.2 million player option.

Since coming to Milwaukee last month, Holiday has been open about his long-term future in Milwaukee and there have been whispers as to his intentions o f potentially signing a contract extension in February.

But until either one or both of those decisions are made, it leaves the Bucks Bucks in a precarious spot with two of their cornerstones not locked down for the long-term future.

All of that makes the 2021 offseason just as crucial as this offseason was for the Milwaukee Bucks and the ability to keep open this championship window.

Plenty of uncertainty could follow Giannis Antetokounmpo, Jrue Holiday and the Milwaukee Bucks going into next offseason.

Without having any guarantees on either Antetokounmpo’s or Holiday’s futures beyond this season, this current iteration we know as the Bucks goes up in smoke and affects their championship aspirations. That certainly can be seen in the anxiety most Bucks fans have in whether Antetokounmpo signs his extension this offseason or goes through with free agency next year.

The Bucks tried to thread a tight needle and assemble a more talented roster to entice Antetokounmpo into signing his extension as soon as this offseason. But their plan did not come without some pain, given the whole ordeal with Bogdan Bogdanovic.

As Antetokounmpo’s teammates and Bucks head coach Mike Budenholzer continue to feild questions regarding the two-time MVP’s future at the start of training camp, the unrest that hangs over the organization adds another layer going into the season. Having already squashed any trade rumors months ago, Antetokounmpo and the Bucks may just ride it out for this season if he elects to forgo signing his supermax extension before the start of the season.

Right now, though, the Bucks have, at minimum, $103.5 million committed on their books for next season and that’s without knowing what Holiday as well as Bryn Forbes ($2.45 million and Bobby Portis ($3.8 million) do with their respective player options. And we should add in the formality that is the Bucks picking up Donte DiVincenzo’s fourth-year option before the start of this season.

With the salary cap set at $112 million and the luxury tax set at $136.6 million for the 2021-22 season, the Bucks have the fallback of using the cap holds of both Antetokounmpo and Holiday to find a max slot for an upcoming free agent, albeit with some maneuvering.

That would be the best-case scenario of not knowing both players’ intentions on staying in Milwaukee long-term and it still comes with plenty of risk. Either way, all Bucks fans should buckle up for what could be an even bumpier offseason next year, even without knowing the answer to the biggest question facing them.