Why Damian Lillard landed in Milwaukee and what comes next

Giannis Antetokounmpo's uncertain future in Milwaukee loomed large over this lengthy summer of Damian Lillard trade talks. His repeated public comments — first to the New York Times, then to the "48 Minutes" podcast — didn't fall on deaf ears. When a two-time MVP loudly claims he's not signing an extension with his incumbent franchise, in part to evaluate if Milwaukee was still as committed to championships as he is, the Bucks and rival front offices certainly heard him loud and clear.

It was thought Toronto and Miami, the two teams most league executives pinned Lillard's sweepstakes between, were attempting to save powder and draft capital in their respective pursuits of Lillard, should Antetokounmpo ever become available before his current deal with the Bucks expires in 2025. Yet in the end, it was Milwaukee that emerged with Lillard and his four-year, $220 million contract, having sent out All-Star point guard Jrue Holiday, a 2029 first-round pick, unprotected swap rights in 2028 and 2030 and more in a three-team trade that also landed Phoenix Suns center Deandre Ayton in Portland, league sources confirmed to Yahoo Sports.

There’s an argument that Milwaukee suffers a significant defensive downgrade in forfeiting Holiday, one of the league’s premier perimeter pests, for Lillard and his deficiencies on that end of the floor. Yet the Bucks’ half-court offense, particularly in the postseason, was in dire need of secondary sizzle behind all of Antetokounmpo’s power toward the rim. Opposing coaches often found Milwaukee predictable and lackluster in those moments, and then watched the Bucks’ scoring sputter in their fateful 4-1 first-round series loss to Miami.

The Bucks’ blockbuster took rival personnel largely by surprise across the NBA. Most of the chatter surrounding Lillard’s future over the last week, as the Blazers increased conversations regarding their All-NBA guard, was centered on Toronto’s legitimate interest and approach for Lillard, sources said, in contrast to Portland’s nonexistent negotiations with Miami. The Bucks quietly sought Lillard in the background of those theatrics, doubling down on the very script Milwaukee followed to satisfy Antetokounmpo before the 2020-21 campaign, when they acquired Holiday from New Orleans.

It’s just too consequential to see a generational player leave your franchise, whether in free agency or by getting valuable pieces back via trade. And if the Bucks were going to take any swing before this season began, you must applaud Jon Horst’s front office for taking the biggest swing imaginable in landing one of the top 75 players in NBA history. In February, there was talk of Milwaukee using its 2029 pick to go after Bojan Bogdanović from Detroit. To turn that selection, plus swaps in 2028 and 2030, into Lillard is a much, much bigger bomb. The Bucks still require depth at guard behind Lillard, where veteran Cam Payne could be an option for the Bucks, league sources told Yahoo Sports.

The fact this deal resulted in a three-team trade, and with Phoenix as the third party, does not come as a surprise. Much of the league was aware of Portland’s interest in swapping center Jusuf Nurkić for Ayton, sources said. The Suns also had lengthy conversations throughout last season with the Bucks regarding Jae Crowder trade frameworks, sources said, as Phoenix personnel conducted due diligence on Grayson Allen, who’s now finally heading to the Suns as part of this mega-deal.

Phoenix continues to spend, second apron be damned. While the entire NBA is steering away from the new collective bargaining agreement’s imposing limitations, the Suns actually added $1.3 million in salary and $4.8 million in luxury tax payments by taking on Nurkić, plus Allen, young swingman Nassir Little and former first-round pick Keon Johnson. The Suns, at this early juncture, are expected to waive Johnson and Ish Wainright, league sources told Yahoo Sports. Phoenix included second-round pick Toumani Camara with its outgoing package in part to maintain the roster flexibility for Jordan Goodwin, the only point guard on the Suns’ roster and a close friend of Bradley Beal’s following their season together in Washington.

Phoenix surely looks at the departure of Ayton as addition by subtraction, not to mention the added depth to a roster that was full of four hefty contracts and minimum deals. The fissures between Ayton and Suns personnel began under former coach Monty Williams, sources said, and seemed headed for further frustrations as the former No. 1 pick was undoubtedly headed to a more limited role behind Beal, Devin Booker and Kevin Durant. Phoenix leadership was not sold on Ayton’s consistency and ability to impact winning amid this franchise’s expensive title chase. Various Suns figures were eager for a change of direction, sources said, from players to front office members, despite new coach Frank Vogel’s opportunity to mold Ayton into a defensive anchor.

The fresh start for Ayton in Portland will be welcomed on his side as well, sources said. For all his naysayers, he remains a naturally gifted 25-year-old with untapped upside. Depending on the Blazers' continued return for Holiday — Portland is exploring trade scenarios in the coming days, sources said — Joe Cronin's front office is at least halfway to a major haul for Lillard many rival teams didn't necessarily believe was there after Lillard and his representation pinpointed Miami so clearly as his preferred destination.

Holiday may even have a wider market than Lillard, not to say he will draw a bigger return. With just one season at $34.9 million guaranteed on his contract before a player option for 2024-25, plenty of teams can welcome the two-way stalwart onto their books, with consideration to a next deal that should decline in value as Holiday’s physicality naturally declines as well.

Could Miami satisfy its wishes for an All-Star point guard by dealing with Portland for Holiday instead of Lillard? That was a repeated talking point among league executives in the aftermath of Wednesday’s trade, although it’s clear the Blazers and Heat did not have significant conversations for much of this summer, league sources told Yahoo Sports, including this past week. Miami, though, has valued Holiday quite highly dating back to his days in New Orleans, sources said.

Perhaps Holiday entering the trade market presents more flexibility for the Sixers and James Harden. Philadelphia has indeed registered its interest in Holiday with Portland, league sources told Yahoo Sports. And there would seem to be an obvious three-team structure that benefits Portland, Philadelphia and Los Angeles, where Holiday returns to the franchise that drafted him, Harden gets his wish and joins the Clippers and the Blazers receive first-round picks from each team. Los Angeles has not been willing to offer more than one selection to Philadelphia for Harden, sources said. The Clippers have also not been willing to include versatile swingman Terance Mann. But if the Sixers and Daryl Morey could spin a potential holdout with Harden into a motivated Holiday, for the cost of one of Philadelphia’s future picks and Harden’s $35.6 million salary, that would bill as fantastic value for all parties involved. But then, maybe the Clippers abandon all pursuit of Harden to go after Holiday in their own right.

How quickly Portland moves on from Holiday of course remains to be seen. There’s clear recent precedent: It took Washington several days to flip Chris Paul to Golden State after netting the future Hall of Famer from the Beal trade to Phoenix. The Blazers took three months to scour the market and hold Lillard for their greatest possible return. Holiday marks the last vestige of Portland’s chances to maximize what comes back for their franchise’s greatest player. If they handle their business in similar fashion, the Blazers are going to look far and wide for what Holiday can add to their treasure chest. From here, it’s a matter of what deal Cronin’s group believes gives Portland that ultimate return.