The Milwaukee Bucks are entering the 2020-21 NBA season in one of the most tense states in their franchise's history. Their ultimate goal would be having Giannis Antetokounmpo accept their supermax extension before the Dec. 21 deadline, which would keep the reigning MVP in the fold for a maximum of five years, with the fifth year being likely optional.
As it stands, the Bucks have at least attempted to do their due diligence in bringing Antetokounmpo some star talent that can make multiple championship runs for years to come. They ended their offseason on fair terms barring any breaking trades that happen. They were also able to move on from some stagnant pieces such as Eric Bledsoe and Ersan Ilyasova.
Yet the talent they brought back doesn't necessarily call for a celebration. As it stands currently, those additions are not much of an upgrade from the surrounding pieces they contained last year. While they don't put you on a decline, they certainly don't increase your winning percentage by a ridiculous margin.
Currently, the Bucks in all honesty are in no better position to sign Antetokounmpo to a supermax extension than they were before the offseason began.
3. Holiday's not the answer for Bucks
While they were able to land Jrue Holiday, who's an immediate upgrade in terms of both Eric Bledsoe and George Hill, they still failed at improving their bench talent as opposed to what they contained last year.
This free agency was set to be one of the weaker ones in recent memory, while being a crumb in comparison to the frenzy of the 2019 offseason. At that point, the Bucks front office's hands were tied in an oversaturated free agent market, which no one is to blame for.
They still were able to move the needle slightly after grabbing DJ Augustin, Bobby Portis and Torrey Craig, all of whom can make immediate impact. Still, those immediate impacts don't bring about championship promises. The player with the most playoff experience in terms of making a deep run is Craig, which points to the lack of postseason experience for the bunch of newcomers.
The Bucks also gave up far too much in exchange for Holiday's services. At the price of three first-round picks, Holiday's value becomes questionable. Those picks may come back to bite Milwaukee in the future if Antetokounmpo does elect to move on from the only franchise he's played for in seven seasons. Keeping at least one or two of those picks could've helped facilitate another deal around the league for more quality coming off the bench.
2. Other suitors got better
The Bucks are a low market team, which means most of their talent is coming in via trades or drafts. They may hold the rare exception of overpaying a free agent in desperation, but for the most part they remain at the bottom of the list for most players simply due to their location.
On the flip side, there are a few teams that have their eyes on Giannis for the 2021 free agency. For the most part, all of those teams have gotten better or remained in their normal contending stature.
The Lakers are still showing championship promise after a successful offseason. They were able to land a few exceptional players on team-friendly deals, which can still leave the door open for signing Antetokounmpo in 2021. The same can be said for Miami. While they didn't retain another star alongside Jimmy Butler, they did maintain most of their championship-appearing roster while adding some key pieces.
This was Milwaukee's time to get in front of the problem before it became one. Now they may just be playing catch up.
1. Failed at landing a third star
The Bucks still don't have another star outside of Antetokounmpo and Khris Middleton. Holiday will definitely bring a different dimension to the backcourt, but he won't be someone that can consistently put up big numbers like perhaps Chris Paul had they traded for him instead.
They had eyes on–and had reportedly signed–Bogdan Bogdanovic via sign-and-trade, but that deal backfired. Now, the Bucks find themselves in the middle of an investigation, seeing as how they “completed” a trade that one party didn't agree to. To make matters worse, Bogdanovic was someone that came highly regarded by Antetokounmpo. The DPOY spent a decent amount of time recruiting Bogdanovic, which surely won't sit well with him in their failed attempts.
While 2021 promises to likely be a bit more entertaining than this offseason, the Bucks may be in the midst of trying to convince an unrestricted Antetokounmpo to re-sign versus going after other star-like quality to pair with him. There were a few disgruntled stars out in the open, some of which could've brought about a different outcome to the Bucks' postseason woes.
At the moment, Milwaukee will be taking the stage with a talent level that closely resembles that of their 2020 squad, which is a problem.
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