Before the NBA Media Day, the Boston Celtics and Milwaukee Bucks completed significant trades to address their backcourt needs. The acquisition saw the Milwaukee Bucks gain 7x All-Star Damian Lillard from Portland, while the Boston Celtics secured Jrue Holiday, a defensive specialist.
Damian Lillard had spent his entire career in Portland. The long-standing saga between Damian Lillard and the Portland Trail Blazers concluded recently. Last July, 33-year-old Lillard expressed his desire to be traded from Portland, where he had been a mainstay for eleven seasons. During his tenure, Lillard led the Trail Blazers to eight playoff appearances but was unable to secure an NBA Championship. Despite several strong playoff runs, Portland only managed to reach the Western Conference Semifinals three times and made one appearance in the Western Conference Finals against Golden State.
Known for his loyalty to Portland, Lillard boasted a career average of 25.5 points, 1 steal, 6.7 assists, and 4.2 rebounds. No. 0 holds several all-time records with the Trail Blazers, including Points (19,376), Offensive Win Shares (86.8), Three-Point Field Goals (2,387), Three-Point Field Goal Attempts (6,410), Free-Throw Attempts (4,946), Free-Throws (4,427), and Player Efficiency Rating (22.5).
Lillard’s time in Portland ended without an NBA Championship title, with the Trail Blazers finishing 33-49 and near the bottom of the Western Conference. Since head coach Chauncey Billips’s appointment, Portland has not made a playoff appearance. Despite Lillard’s repeated desire to play alongside other star players, the Trail Blazers elected to retain the third overall pick in the NBA Draft Lottery. With a crowded backcourt that included Lillard, Anfernee Simons, and Shaedon Sharpe, the organization drafted guard Scoot Henderson from G-League Ignite, indicating that he is seen as Lillard’s successor.
Portland had the opportunity to improve and build a championship roster, having signed Jerami Grant to a $160 million, five-year contract. However, less than ten days after this signing, Lillard requested a trade. During his stint in Portland, Lillard became a consensus 7x NBA All-Star, won the 2012-2013 Rookie of the Year, and was honored as a member of the NBA 75th Anniversary team. In the most recent season, the point guard achieved a career-high points per game average of 32.2.
Reports surfaced about Lillard’s preferred destination being the Miami Heat. However, Portland General Manager Joe Cronin was clear that Lillard would only be traded for the right package, which had to include a “star-level return.” Despite Lillard’s inclination, trade negotiations with the Miami Heat and Milwaukee Bucks did not materialize. Additionally, Lillard’s agent’s attempts to steer several NBA teams toward his preferred landing place brought Lillard close to facing disciplinary action. According to Shams Charania of the Athletic, Miami was ready to make an offer in the summer, offering up to three first-round draft picks, along with Tyler Herro to a third team, and multiple second-rounders and swaps, along with expiring contracts and 2022 first-round pick Nikola Jović. However, the Blazers showed little interest in these negotiations, leading to a strained relationship between the two parties.
As the months passed, trade talks stagnated. At one point, Lillard considered returning to his hometown. Reports indicated that Joe Cronin had every intention of trading Dame . Despite the ambiguity surrounding these negotiations, Damian Lillard made it clear that his relationship with the Trail Blazers front office had been soured. Following his trade, No. 0 announced his move via his Twitter account, focusing on addressing the Blazers fans and the city of Portland, expressing his excitement for the next chapter with the Bucks.
The Milwaukee Bucks emerged as the “secret” team to secure Lillard in the East, making a three-team trade that also involved the Phoenix Suns and Portland Trail Blazers just days before the start of training camp. In this trade, Portland acquired Deandre Ayton and Toumani Camara from the Suns, Jrue Holiday from the Bucks, and a 2029 first-round pick from Milwaukee while also securing two first-round pick swaps with the Bucks in 2028 and 2030.
Phoenix received Grayson Allen from Milwaukee, along with Keon Johnson, Nassir Little, and Jusuf Nurkic from the Blazers. Lillard now joins Giannis Antetokounmpo, one of the best players in the league, to pursue championship aspirations with the Bucks, the most recent NBA Champions in 2021. This transfer reshapes the landscape of the Eastern Conference by solidifying the Bucks as favorites to win the NBA title.
Damian Lillard’s arrival sparked a grand welcome from the Milwaukee community, with thousands of fans gathering outside the stadium for his welcome rally. Eye-catching “It’s Dame Time, Milwaukee!” billboards surfaced three days after the trade announcement, and Lillard, joined by his two children, made his first public appearance in a vibrant green sports outfit during the event. On Media Day, Lillard expressed his excitement about the trade and his newfound association with Milwaukee, portraying it as a fresh and welcoming experience for him and his family.
Lillard expressed his anticipation about teaming up with 2x MVP Giannis Antetokounmpo, forming one of the most formidable duos since the days of Oscar Robertson and Kareem Abdul-Jabbar. He also emphasized his desire for winning, stating that his arrival at Milwaukee was propelled by a mutual goal to win, an opportunity that he is extremely thankful for. Lillard also appreciated the warmth shown by the Bucks towards his family and praised the familial environment he experienced from the outset. His sentiments about feeling wanted and comfortable highlight the positive impression of his entry into the Bucks organization.
Following this significant acquisition, the Milwaukee Bucks became immediate frontrunners to clinch the NBA title, signaling a power shift within the Eastern Conference. In a surprising turn of events, the Portland Trail Blazers subsequently traded Jrue Holiday to the Boston Celtics, further levelling the playing field in the East. The Celtics acquired Holiday, sending Robert Williams III, Malcom Brogdon, and two future first-round picks to the Blazers, thereby enhancing their title prospects as well. Previously, Boston was viewed as the dominant force in the Eastern Conference, but these trades have redefined the landscape and positioned both the Bucks and Celtics as equally probable contenders for the championship.
Lillard’s arrival in Milwaukee has infused the Bucks with championship aspirations, elevating them into a superteam that is primed for success. His partnership with Giannis Antetokounmpo offers the potential to be one of the most formidable pick-and-roll duos in the league. Expressing his excitement about playing alongside Giannis, Lillard revealed that he had never encountered such an opportunity before. Amidst the team’s notable talent, Lillard clearly understands his role and emphasized the importance of establishing chemistry alongside the existing hype. While acknowledging his consistent underdog status throughout his career, Lillard hinted at a sense of fulfillment and readiness, stressing the need to convert potential into achievements at this stage of his career.
Similarly, the addition of Jrue Holiday to the Boston Celtics bolsters their backcourt, injecting defensive intensity and exceptional playmaking skills. Described as an “assassin” by Jaylen Brown, Holiday’s defensive prowess and playmaking abilities are anticipated to elevate the Celtics’ championship aspirations significantly. Serving as a complementary force alongside the team’s standout players, Holiday joins a formidable roster that includes Jayson Tatum, Jaylen Brown, Kristaps Porzingis, Al Horford, and Derrick White. Concluding their Eastern Conference Finals disappointment from the previous season, the Celtics have made a substantial upgrade at the point guard position, fortifying their championship ambitions and creating a balanced rivalry with the Bucks. The acquisitions of Lillard and Holiday have redefined the Eastern Conference landscape, presenting both Milwaukee and Boston as equally potent forces vying for the ultimate prize.
