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Why Damian Lillard Chose Milwaukee and What’s on the Horizon

The Milwaukee Bucks faced an uncertain future with Giannis Antetokounmpo, and this uncertainty became the focal point during the extended summer of Damian Lillard trade discussions. Giannis, a two-time MVP, made his intentions clear through public statements, including interviews with the New York Times and the “48 Minutes” podcast. His reluctance to sign an extension with the Bucks stemmed from his desire to assess the franchise’s commitment to championship aspirations.
These declarations didn’t go unnoticed by both the Bucks’ management and rival front offices. When a player of Giannis’s caliber hints at potential departure, it sends shockwaves across the league. Teams like Toronto and Miami, long considered frontrunners in the Lillard sweepstakes, were keeping a close eye on the situation, aiming to preserve their assets for a possible pursuit of Giannis, should he become available before his contract with the Bucks expires in 2025.
However, in a surprising turn of events, it was the Milwaukee Bucks who secured Damian Lillard and his lucrative four-year, $220 million contract. This move came at the cost of All-Star point guard Jrue Holiday, a 2029 first-round pick, unprotected swap rights in 2028 and 2030, and additional assets in a three-team trade. As part of this trade, the Portland Trail Blazers also acquired Deandre Ayton from the Phoenix Suns, according to sources familiar with the deal.
Critics argue that Milwaukee might suffer a defensive setback by parting ways with Jrue Holiday, known for his tenacious perimeter defense, in exchange for Damian Lillard, who has certain defensive limitations. Nevertheless, the Bucks were in dire need of offensive firepower in their half-court game, especially during the playoffs. Opposing coaches often found their offense predictable and lackluster, ultimately resulting in their disappointing 4-1 first-round series loss to the Miami Heat.
The Milwaukee Bucks’ surprising move sent shockwaves through the NBA community. The recent buzz surrounding Damian Lillard’s future centered mainly on the Toronto Raptors’ keen interest in acquiring the All-NBA guard. In contrast, discussions with the Miami Heat seemed nonexistent. However, under the radar, the Milwaukee Bucks were quietly pursuing Lillard, reminiscent of their strategic approach to satisfy Giannis Antetokounmpo before the 2020-21 season when they acquired Jrue Holiday from the New Orleans Pelicans.
Losing a generational player, whether in free agency or via trade, is a significant blow to any franchise. The Milwaukee Bucks, faced with this reality, made an audacious move to secure one of the NBA’s top 75 players in history. This move involved leveraging their 2029 draft pick and swap rights in 2028 and 2030 to acquire Damian Lillard, a massive upgrade. While the Bucks still need depth at the guard position alongside Lillard, sources suggest that veteran Cam Payne could be a potential option for the team.
The fact that this deal unfolded as a three-team trade with the Phoenix Suns involved shouldn’t come as a surprise. The league had been aware of Portland’s interest in trading center Jusuf Nurkić for Deandre Ayton. Additionally, the Suns had engaged in discussions with the Bucks throughout the previous season regarding Jae Crowder trade scenarios. Phoenix was also conducting due diligence on Grayson Allen, who is now part of this blockbuster trade.
Despite the league’s move away from the new collective bargaining agreement’s constraints, Phoenix continued to spend, absorbing significant salary and luxury tax payments by acquiring Nurkić, Allen, Nassir Little, and Keon Johnson. The Suns are expected to waive Johnson and Ish Wainwright, maintaining roster flexibility for Jordan Goodwin, the only point guard on their roster, and a close friend of Bradley Beal from their time together in Washington.
Phoenix sees Ayton’s departure as a positive step, adding depth to a roster filled with high-value contracts. Differences between Ayton and Suns personnel had emerged under former coach Monty Williams, casting doubt on his ability to contribute to the team’s championship aspirations. Despite new coach Frank Vogel’s potential to develop Ayton into a defensive anchor, the desire for change was palpable among Suns players and front office members.
The fresh start in Portland is expected to benefit Ayton, a gifted 25-year-old with untapped potential. Meanwhile, the Blazers are exploring trade scenarios involving Holiday as part of the ongoing deal. This move comes as a surprise, considering Lillard’s previous preference for Miami.
Jrue Holiday’s market value may be broader than Lillard’s, although the return may not necessarily be larger. With just one guaranteed season at $34.9 million before a player option for 2024-25, many teams are interested in acquiring the versatile guard.
Could Miami, aiming for an All-Star point guard, explore a trade for Holiday rather than Lillard? While the Blazers and Heat had limited conversations this summer, sources indicate that Miami highly values Holiday, dating back to his days in New Orleans.

Holiday’s availability in the trade market could also open up opportunities for the Philadelphia 76ers and James Harden. Philadelphia has expressed interest in Holiday, potentially leading to a three-team deal involving the Blazers, 76ers, and the Los Angeles Clippers. Such a deal could reunite Holiday with the team that originally drafted him, fulfill Harden’s desire to join the Clippers, and provide the Blazers with valuable first-round picks. However, negotiations with the Clippers have faced challenges, as they are reluctant to part with versatile swingman Terance Mann.

The timeline for Portland’s move involving Holiday remains uncertain. Previous transactions, such as Chris Paul’s trade to Golden State after the Beal trade to Phoenix, suggest that it could take some time. The Blazers are committed to maximizing the return for their franchise’s greatest player, Damian Lillard. As they navigate the trade landscape, it’s a matter of finding the deal that best aligns with their ultimate objectives.

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