This offseason has been a mixed bag for the Milwaukee Bucks so far. After swinging a blockbuster trade with the New Orleans Pelicans for Jrue Holiday, they thought they had another massive deal lined up to acquire Bogdan Bogdanovic. Only, that fell apart and they had to scramble to come up with a Plan B for filling out the rest of their roster. They wound up with DJ Augustin, Bobby Portis, Bryn Forbes and Torrey Craig, then re-signed Pat Connaughton.
In terms of regrouping on the fly, it was a passing grade. But their offseason won't be judged on managing to find solid veterans to come off the bench, but rather on whether or not Giannis Antetokounmpo signs his five-year, $228 million supermax extension. And on those terms, it remains to be seen whether the Bucks did a good enough job, though they believe they did, according to ESPN's Brian Windhorst:
Internally, league sources said, the Bucks have gone from cautiously optimistic to cautiously confident in recent weeks that the outcome will be favorable when Antetokounmpo returns from Greece, where he has been since mid-September.
Obviously nothing is final until he puts the pen to paper, but this is good news for Bucks fans. And there are multiple signs that point to Milwaukee's front office being correct.
First of all, the Bucks dumped an incredible amount of draft capital to get Holiday, sending three first-round picks and two future pick swaps to the Pelicans. For comparison, that's the same amount of picks and pick swaps that the Los Angeles Lakers gave up to get Anthony Davis. Doing that for Holiday -- a very good player but not one of the league's best -- is somewhat reckless, unless you know it will convince Giannis to stay, at which point it becomes a perfectly reasonable trade.
Then, of course, there's the fact that Giannis would make an additional $83 million in guaranteed money by signing the supermax extension than he would by signing somewhere else in free agency. The back-to-back MVP said recently that he doesn't care about the money, but it's one thing to say that as an abstract idea, and another to actually turn down such a substantial figure when it's presented to you.
Giannis has until Dec. 21 to sign the extension this year, and if he does, it will cement the Bucks as title contenders for the foreseeable future. If not, and the Bucks' confidence was misplaced, this will be perhaps the most stressful season in the history of the franchise.