Acquiring Damian Lillard required pushing all the chips to the table and the Milwaukee Bucks saw luxury-tax aprons on one side, with Giannis Antetokounmpo's possible eye wandering on the other. The longer the Miami Heat and Portland Trail Blazers went without consummating a deal, particularly with training camp looming and nobody wanting a PR disaster if Lillard showed up to camp, the more the odds increased for someone to step in and realize Lillard was worth the chance.
The Bucks, sitting idly by as the clock ticks on Antetokounmpo's impending free agency, didn't want to let their Miami tormentors increase the mental space between the two by watching Lillard fly south.
And good for them. There’s no rule that claims the Bucks shouldn’t inquire on Lillard when Lillard asks out, and his tune changed in the last couple weeks when it appeared there wouldn’t be real traction between Miami and Portland.
The water had been poisoned for weeks now, with Lillard insisting on going to Miami and Portland insisting on refusing to deal him there. Lillard’s loyalty to Portland wasn’t worth the price of the phone he used to tweet from, even if it seemed like he was the one player who would’ve gotten sent to a desired destination because of his previous service as opposed to being put under the umbrella of that nasty phrase, “player empowerment.”
The deal doesn't look like Milwaukee knocked Portland's socks off — Jrue Holiday will have to be moved before one can truly evaluate the Trail Blazers' haul in this. Holiday, arguably the league's best defensive guard, told the media in Milwaukee on Tuesday he wanted to remain a Buck for the rest of his career.
Today, he’s sent away — albeit a champion and beloved figure, with very little agency to his future, and no regard to his own connection to a place he’s learned to call home.
The other side of player empowerment, the umbrella that doesn’t keep everyone safe from rain.
The real empowerment lies with the two-time MVP, the man who’s in the short conversation as the game’s best, Antetokounmpo. It’s slightly different from a few years ago, when Anthony Davis loudly asked out of New Orleans with one place in mind, Los Angeles — with LeBron James being the most powerful figure in the league at that time.
James had the sway, always has. Now, Antetokounmpo is flexing, albeit subtly. He let it be known he wasn’t content with the Bucks merely being a contender, resting on the laurels of an excellently built roster headed by general manager Jon Horst.
Excellent but not excelling in May and June. Knocked out in the second and first rounds, respectively, since winning the 2021 title. And once a team wins a title with the superstar still in tow, that becomes the standard — Khris Middleton’s wrist injury (2022) or Antetokounmpo’s ailments be damned.
So, the Bucks quietly began poking around the matter two weeks ago, league sources told Yahoo Sports. A deal of this manner — involving multiple teams and a player of Lillard’s stature required discretion. They waited out the dalliance with Toronto Raptors that came and went, before putting the finishing touches on an agreement Wednesday afternoon.
Antetokounmpo’s present and future loom over this deal, and apparently, Bucks ownership had no qualms about acquiring a player in Lillard who’s owed over $215 million over the next four years compared to Holiday, who has a player option this summer he can exercise or try to negotiate an extension with his next club — certainly not the Blazers.
Antetokounmpo led the league in usage rate for the second time in his career, in large part due to Middleton’s extended absence. But that isn’t a recipe for winning championships — in fact, it’s indicative of having a star worn down when the games really matter and a sign that some type of decline is approaching.
Antetokounmpo having late-game help — a player who yearns for the big moment, who doesn’t need to be set up while also being able to facilitate others — seems like a match made in heaven for the time being.
The pressure is still on both to consummate this marriage and not just get to the Finals, but to win it. Until Antetokounmpo signs a long-term extension with the Bucks, the clock will be ticking, his words will be analyzed and dissected like Dame D.O.L.L.A. song lyrics.
And losing Holiday is no minor measure for the Bucks. One could argue he was the author of the biggest — or second-biggest — play in franchise history, his strip of Devin Booker and subsequent lob to Antetokounmpo to seal Game 5 of the 2021 NBA Finals, giving the Bucks a 3-2 lead and cementing himself as a stone-cold big-game player.
Lillard is an assassin, he just does it in a different way, a way the Bucks have not had since Antetokounmpo has become the center of the franchise.
You could stick the low-maintenance Holiday on virtually any perimeter star in the league, and feel reasonably comfortable that your defense won’t be compromised. Lillard isn’t that brand of defender, although one would think he would rise to the level of accountability playing with Antetokounmpo demands. It’s the same internal accountability that would’ve been waiting for him in Miami, with Erik Spoelstra, Jimmy Butler and Bam Adebayo.
But Portland was so turned off by either Lillard’s approach or his public desire to go to Miami, they weren’t willing to engage. And perhaps Miami felt no one was willing to pay the freight for Lillard, so the Heat took a hard line believing Portland would come back to the table in good faith.
It doesn’t appear to be high-stakes thievery by any team in this three-team deal, with question marks all around. Can Portland salvage Deandre Ayton while developing Scoot Henderson, Shaedon Sharpe and Anfernee Simons? Phoenix got pieces back to replenish a little depth after being depleted in deals to acquire Kevin Durant and Bradley Beal, but will it be enough to get through the treacherous West?
Portland has some measure of pride in not being bullied by its franchise player, but the long-term prospects are still murky. Milwaukee has retooled on the fly, with this blockbuster after replacing its coach with Adrian Griffin months ago.
All that’s left is for Antetokounmpo to hold up his end of the bargain, and for Lillard to fulfill the promise his talent calls for.