The Milwaukee Bucks made headlines last offseason by acquiring All-Star point guard Damian Lillard in a blockbuster trade involving the Portland Trailblazers and Phoenix Suns. In this deal, Milwaukee sent shooting guard Grayson Allen to Phoenix and Jrue Holiday to Portland, a move made without consulting two-time MVP Giannis Antetokounmpo, who was close to Holiday. Giannis expressed no dissatisfaction but acknowledged the emotional complexity, stating, “I love him as a brother.”
As anticipated, the Trailblazers, not planning to retain Holiday, sought a trade. Holiday provided a list of preferred destinations, leading to his trade to the Boston Celtics in exchange for former Bucks guard Malcolm Brogdon, Robert Williams, and multiple first-round picks. In his debut season with Boston, Holiday averaged 12.5 points, 5.4 rebounds, and 4.8 assists per game, earning Second Team All NBA Defense honors and finishing sixth in Defensive Player of the Year voting.