The Boston Celtics’ pursuit of Giannis Antetokounmpo carries a major risk beyond losing out on the two-time MVP: damaging their relationship with Jaylen Brown.
As the league prepares for the June 23 NBA Draft and trade discussions around Antetokounmpo accelerate, ESPN’s Brian Windhorst cautioned that Boston has not necessarily made a firm offer involving Brown. Barry Jackson reported Monday that the Celtics’ hesitation is tied to the possibility of a deal collapsing after Brown becomes aware he was seriously discussed.
“If something does not materialize,” Bobby Marks warned on ESPN, the Celtics “ought to be awfully careful” with Brown if he knows he was offered in trade talks.
Brown has become the centerpiece of Boston’s championship foundation alongside Jayson Tatum. The 29-year-old forward averaged 28.7 points, 6.9 rebounds and 5.1 assists in 71 games during the 2025-26 season, earning All-NBA Second Team honors and finishing sixth in MVP voting. He shot 47.7% from the field while helping Boston finish 56-26, win the Atlantic Division and secure the Eastern Conference’s No. 2 seed.
The Celtics’ interest in Antetokounmpo is understandable. The Bucks fell to 32-50 in 2025-26 and missed the playoffs, creating uncertainty around the future of the franchise’s centerpiece. Reports have indicated Antetokounmpo would be open to signing a long-term extension with Boston or Miami if traded, but acquiring him would require a significant package.
Milwaukee’s potential interest in Brown complicates the situation. League sources told Marc Stein that the working expectation around the NBA is that the Bucks would prefer to move Brown again for younger players and draft assets rather than make him the face of their next era.
That approach reflects Milwaukee’s rebuilding challenges. The Bucks lack the flexibility of a typical rebuilding team after previous moves, including the trade that brought Damian Lillard, limited their future draft capital. A Brown-centered return could potentially be converted into additional young talent and picks rather than keeping a veteran on a massive contract.
Boston would also need a third team to make the numbers work. Previous reporting has suggested Milwaukee may prefer a broader asset package, while Portland has emerged as a possible facilitator because of its draft resources connected to Milwaukee.
For the Celtics, the risk is clear. Brown is under contract through the 2029-30 season on a five-year, $285 million extension and remains one of the NBA’s most valuable two-way wings. A failed Giannis pursuit could leave Boston with the same roster it started with but a potentially unhappy star.
