Giannis Antetokounmpo’s uncertain future in Milwaukee played a big role in this long summer of trade talks with Damian Lillard. His repeated public comments — first to the New York Times, then to the “48 Minutes” podcast — did not fall on deaf ears. When a two-time MVP loudly asserts that he’s not signing a contract extension with his established franchise, in part to gauge whether Milwaukee is still as interested in championships as he is, the Bucks and rival front offices certainly heard him loud and clear.
It was assumed that Toronto and Miami, the two teams between which most league executives had drawn Lillard’s sweepstakes, were trying to conserve powder and capital in their respective pursuits of Lillard should Antetokounmpo ever become available before his current contract with the Bucks expires in 2025. But in the end, it was Milwaukee that emerged with Lillard and his four-year, $220 million contract after acquiring All-Star point guard Jrue Holiday, a 2029 first-round pick, unprotected trade rights in 2028 and 2030 and more in a three-team trade that also included center Deandre Ayton moving from the Phoenix Suns to Portland, league sources confirmed to Yahoo Sports.
There’s an argument that Milwaukee takes a significant defensive hit by giving up Holiday, one of the league’s greatest perimeter pests, because of Lillard and his deficiencies on that end of the court. But the Bucks’ half-court offense, especially in the postseason, desperately needed secondary momentum behind Antetokounmpo’s power toward the rim. Opposing coaches often found Milwaukee predictable and lackluster in those moments, then watched as the Bucks faltered in their fateful 4-1 first-round loss to Miami.
The Bucks may have felt backed into a corner when they bolstered Giannis Antetokounmpo’s roster with Damian Lillard. (Photo by Abbie Parr/Getty Images) (Abbie Parr via Getty Images)
The Bucks’ blockbuster largely surprised rivals across the NBA. Most of the talk about Lillard’s future in the last week, as the Blazers ramped up talks about their All-NBA guard, focused on Toronto’s legitimate interest and approach to Lillard, according to sources, as opposed to Portland’s nonexistent negotiations with Miami . The Bucks were quietly scouting for Lillard in the background of those theatrics, falling back on the exact playbook Milwaukee followed to keep Antetokounmpo happy before the 2020-21 season when they acquired Holiday from New Orleans.
It’s just too consequential when a generational player leaves your franchise, whether in free agency or by getting valuable pieces back through trade. And if the Bucks were to pull off a swing before this season began, you have to applaud Jon Horst’s front office for pulling off the biggest swing imaginable and acquiring one of the 75 best players in NBA history. There was talk in February that Milwaukee would use its 2029 pick to pursue Detroit’s Bojan Bogdanović. Converting that pick plus swaps into Lillard in 2028 and 2030 is a much, much bigger bombshell. The Bucks still need coverage depth behind Lillard, where veteran Cam Payne could be an option for the Bucks, league sources told Yahoo Sports.
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The fact that this deal resulted in a trade between three teams and Phoenix as the third party is no surprise. Much of the league was aware of Portland’s interest in trading center Jusuf Nurkić for Ayton, sources said. According to sources, the Suns also had lengthy discussions with the Bucks last season about the Jae Crowder trade deal, while Phoenix staff conducted due diligence on Grayson Allen, who is now finally joining the Suns as part of this mega deal changes.
Phoenix continues to spend money, second apron be damned. While the entire NBA is moving away from the implicit restrictions of the new collective bargaining agreement, the Suns have actually added $1.3 million in salaries and $4.8 million in luxury tax payments by adding Nurkić as well as Allen, young swingman Nassir Little and signed former first-round pick Keon Johnson. The Suns are expected to be without Johnson and Ish Wainright at this early stage, league sources told Yahoo Sports. Phoenix included second-round pick Toumani Camara in its departure package in part to maintain roster flexibility for Jordan Goodwin, the only point guard on the Suns’ roster and a close friend of Bradley Beal after their season together in Washington.
Phoenix certainly views Ayton’s departure as an addition by subtraction, not to mention added depth to a roster that consisted of four large contracts and minimal deals. The divisions between Ayton and Suns staff began under former coach Monty Williams, according to sources, and appeared to lead to further frustrations as the former No. 1 pick was undoubtedly headed for a more limited role behind Beal, Devin Booker and Kevin Durant. Phoenix leadership was not convinced of Ayton’s consistency and his ability to contribute to victory in this franchise’s expensive title game. Various Suns figures were eager for a change of direction, sources said, from players to front office members, although new coach Frank Vogel had the opportunity to mold Ayton into a defensive anchor.
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The new beginning for Ayton in Portland is also welcomed by his side, sources said. Despite all his critics, he remains a gifted 25-year-old with untapped potential. Depending on the Blazers’ continued holiday return – Portland is exploring trade scenarios in the coming days, according to sources – Joe Cronin’s front office is at least halfway to a big win for Lillard, who many rival teams didn’t necessarily believe would be the case after Lillard and There was His presentation clearly named Miami as his favorite travel destination.
Holiday may even have a bigger market than Lillard, but that doesn’t mean he’ll get a bigger return. Since his contract only has one season guaranteed at $34.9 million before receiving a player option for 2024-25, many teams can welcome the two-way star to their books and consider a next deal that increases in value should lose, as Holiday’s physical performance naturally decreases as well.
Could Miami get its wish for an All-Star point guard by turning to Portland instead of Lillard for Holiday? That was a recurring topic of conversation among league executives after Wednesday’s trade, although it’s clear the Blazers and Heat haven’t had any meaningful discussions for most of this summer, league sources told Yahoo Sports, including last Week. However, according to sources, Miami has held Holiday in high regard since his time in New Orleans.
Perhaps Holiday’s entry into the trade market provides more flexibility for the Sixers and James Harden. Philadelphia has indeed expressed interest in Holiday with Portland, league sources told Yahoo Sports. And there seems 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 are first-rounders from each team -Get picks. According to sources, Los Angeles was unwilling to offer Philadelphia more than one pick for Harden. The Clippers also weren’t willing to add versatile swingman Terance Mann. But if the Sixers and Daryl Morey could turn 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 be fantastic value for everyone involved. But perhaps the Clippers will give up pursuing Harden to pursue Holiday themselves.
Of course, how quickly Portland says goodbye to Holiday remains to be seen. There is a clear recent precedent: It took Washington several days to trade Chris Paul to Golden State after acquiring the future Hall of Famer from the Beal trade to Phoenix. It took the Blazers three months to scour the market and retain Lillard for their best possible return. Holiday marks the last vestige of Portland’s chances of maximizing what comes back for its franchise’s best player. If they conduct business in a similar manner, the Blazers will be looking far and wide for what Holiday can add to their treasure chest. From here, it comes down to which deal Cronin’s group believes will give Portland the ultimate return.