Giannis Antetokounmpo of the Bucks is a free agent after next season, and the team seems to be doing its best to make sure he stays in Milwaukee. Ashley Landis/Pool Photo via the Associated Press

The Milwaukee Bucks crashed the opening of NBA business under cover of darkness, delivering a big jolt to the NBA.

The Bucks emptied their stash of draft picks for the foreseeable future and landed Jrue Holiday from the New Orleans Pelicans. They then cashed in role players to bring Sacramento Kings sharpshooter Bogdan Bogdanovic, improving the starting lineup around MVP Giannis Antetokounmpo and delivering on a promise to pursue a championship rather than rest on their laurels.

In the meantime, the Boston Celtics sit on the sideline, watching as any future trip to the NBA finals become an ever greater challenge.

The hurdle has been raised in front of the Celtics, and it’s not just Milwaukee trying to block their path.

The Brooklyn Nets and Philadelphia 76ers are already addressing weaknesses and the Nets seem to have an inside track on trading for James Harden. Now the possibility of Antetokounmpo leaving – and maybe even being a player in that sweepstakes – seems to be disappearing. Any playoff run the Celtics are going to make over the course of the Jayson Tatum and Jaylen Brown era is going to be a rough gauntlet from start to finish, and that’s now magnified with Antetokounmpo seemingly spending his prime years in Boston’s way.

Danny Ainge, Boston’s president of basketball operations, surely has moves that he wants to make, even though he didn’t have the assets to compete with what Milwaukee just pulled off. It will be interesting to see how Ainge responds, or if he can even come up with a counter-move. If he can’t, Boston might be stuck in the middle of the pack for while.

The Bucks are not stuck. On one end of the equation, it seems ludicrous to suggest a deal that sends five players (Eric Beldsoe, George Hill, Dante DiVincenzo, Ersan Ilyasova, and D.J. Wilson) and what could be five first-round picks (This year’s pick from Indiana, unprotected 2025 and 2027 first-round picks, and pick swaps in 2024 and 2026) for Holiday and Bogdanovic is fair for the Bucks at all.

If you look at it from the perspective of everything going out, it’s an outrageous price to pay for those two players.

However, he big prize in all of this isn’t those two players. It’s keeping Giannis Antetokounmpo and making sure he believes this is a team that will fix what is broken to pursue a title.

Marc Stein of the New York Times tweeted “The last two weeks have been filled with chatter that Giannis Antetokounmpo indeed plans to sign his five-year supermax with the Bucks before the Dec. 21 deadline to do so. The Bucks just made a trade that suggests they must believe it.”

The Bucks don’t get many Giannises floating through town. Even when they have salary cap room to spend, it’s pretty unlikely they’re going to be any MNA superstar’s first choice. Now that they have Antetokounmpo there, and it seems he’s willing to stay, they have little choice but to make some high-risk moves in order to make him happy. It’s hard to win a championship without an MVP candidate on the roster, and he’s won two straight. Milwaukee’s time is now.

What the Bucks get in Holiday is a proven performer who can defend just as well, or better, than Bledsoe but who doesn’t fear playoff moments. He can drive and distribute, and the Bucks hope is that with more space created by Antetokounmpo and others, he can improve his outside shooting. Earlier in his career, he shot somewhere between 36% and 38% but that has tailed off in recent years.

Losing Hill’s 46% shooting will hurt a little, but Bogdanovic is certainly going to make up for some of that and he is a much more willing shooter, taking a 3-pointer 25% of the time he was on the floor as compared to Hill’s 13.8%. Again, playing alongside Antetokounmpo will give him more open looks, so he’ll likely see a little bump in his 37% shooting.

Add to this mix Khris Middleton, who was an All-Star for the past two seasons, and Brook Lopez, who has mastered patrolling the paint and protecting the rim, and the Bucks have now solidified a better starting lineup than they have in years past.
Yes, they have a bench to build, but they’re good enough now to find potentially cheap help from ring-chasing veterans who can fill some gaps.

It’s not a perfect team, but it’s a team that seems to be able to keep Antetokounmpo around for a while.