With Damian Lillard Trade, Bucks Masterfully Answer Giannis’s Call to Win Now

After a first-round playoff exit, Milwaukee addressed several needs with a move for the Portland star, and may have just convinced Antetokounmpo to stick around.

Milwaukee wins.

Miami loses.

And Damian Lillard will get his chance to compete for a championship.

The months-long standoff between Lillard and the Trail Blazers is over. Lillard is headed to Milwaukee, part of a three-team deal that will send DeAndre Ayton, Jrue Holiday and some draft capital to Portland and a handful of rotation players to Phoenix.

It is, unequivocally, a win for Milwaukee. The Bucks didn’t need Lillard. They won a championship in 2021, with Holiday playing a key role. They were a 58-win team last season with the guts of it coming back. But a shocking first-round exit followed by some not-so-subtle public pressure from Giannis Antetokounmpo convinced Bucks brass they needed to do something. Quickly.

Sheesh, did they. Lillard is an upgrade. That’s not a swipe at Holiday, a 19-point-per-game scorer, an elite defender, an All-Star last season. But when Milwaukee has stumbled in the playoffs the Bucks halfcourt offense has often been the reason why. Lillard solves that. He’s a 32-point-per-game scorer. A 37% three-point shooter. A player most comfortable in clutch moments.

You thought Antetokounmpo was difficult to guard before?

Try defending him with Lillard on the floor.

The Bucks will lose something defensively. But Antetokounmpo and the ageless Brook Lopez will erase a lot of mistakes. They will need to replenish some of the lost depth. But Pat Connaughton, Jae Crowder and Malik Beasley are still around, and if a veteran or two hits the market after the trade deadline, the Bucks will be frontrunners to sign him.

Lillard (left) is coming off a career-best season after averaging 32.2 points per game last year.  :: Soobum Im/USA TODAY Sports

For Jon Horst, this is a masterstroke. The Bucks GM didn’t draft Antetokounmpo—John Hammond gets the credit for that—but in six years on the job, Horst has boldly built a winner around him. In 2020, Horst swapped three first-round picks for Holiday. Months later, thanks in no small part to Holiday’s pesky defense, Milwaukee celebrated a championship. Lillard comes with risk—he’s 33, owed $200 million over the next four seasons and has a recent injury history—but he averaged a career high in scoring last season and will undoubtedly be energized playing for a contender.

Giannis, too. The double whammy in all this is not only does Milwaukee improve its chances of winning next season, it also gives Antetokounmpo reason to stick around a lot longer. The Bucks have given Antetokounmpo everything. They have paid him. Promoted him. Signed every basketball-playing member of his family. When the team needed an infusion, they got Holiday. When the team needed a shakeup, they traded for Lillard. Giannis is extension eligible. The Bucks have given him every reason to sign one.

For rivals, that would be devastating. Antetokounmpo’s offseason comments offered a flicker of hope that he might be ready to relocate. The Knicks took notice. The Nets, too. Miami, forever in pursuit of stars, dreamed of Antetokounmpo on South Beach. Those dreams are dead. At the ’23 All-Star game, Antetokounmpo, one of the captains, selected Lillard with his first pick. He isn’t going to like playing with Lillard. He’s going to love it.

And Miami? No, the team can’t be blamed for toxic Heat Twitter—er, X. Or the exasperating ire of certain members of Miami media who couldn’t accept the possibility that Blazers GM Joe Cronin could find a better deal. Ensconce yourself in a Miami Beach bubble and you’d think Portland would be lucky to come away with Tyler Herro and a couple of first-round picks.

Reality, though, was different. Miami wasn’t willing to push all its assets to the middle, and they paid for it. Cronin liked Ayton, a maligned figure in Phoenix but a center who, at 25, averaged 18 points and 10 rebounds as a third option last season. He gambled that a Bucks pick five years will be more valuable than Miami’s. And he’s betting he can collect more with Holiday. There will be a bidding war for Holiday in the coming weeks. The Clippers. The Sixers. The Celtics. The Heat, once the whiplash is gone, will get in the mix. Cronin can get one first-rounder for Holiday. If he plays it right, he could get two.

And Miami? If they can’t land Holiday—and the guess here is that Kyle Lowry and two first-round picks will be the asking price—they will come away with nothing. Max Strus gone, Gabe Vincent, too, and the player they waited all summer for will suit up for a conference rival. Jimmy Butler is still a star, but he’s 34 and a 55–65 game-per-season player. His supporting cast is both diminished and aging. His best chance to win in Miami now is to hope Joel Embiid wants to relocate.

Lillard is relocating and, unsurprisingly, doesn’t sound upset about it. “Excited for my next chapter,” Lillard posted on Wednesday, tagging the Bucks. Lillard may have wanted Miami but he wants to win more, and with the 28-year old Antetokounmpo, he has that chance. For Milwaukee, the championship window is wide open. For the Heat, it may have just slammed shut.