The sight of Jaylen Brown holding up a Philadelphia 76ers jersey did not sit well with Bill Simmons.
As Brown posed for photographs during his introductory press conference on August 6, Simmons posted the video on X with an emphatic three-word message: “I HATE THIS.”
The reaction was brief, but there was little ambiguity behind it. Simmons, a longtime public Celtics supporter, was watching one of the defining Boston players of the last decade formally begin his next chapter with an Eastern Conference rival.
Brown’s introduction came roughly a month after the Celtics traded him to Philadelphia for Paul George, two first-round selections and two second-round selections. The deal officially ended Brown’s 10-season Boston tenure and broke up his championship partnership with Jayson Tatum.
For Celtics followers, the press conference supplied an uncomfortable visual that the initial transaction could not: Brown wearing Philadelphia colors and discussing how he intends to help the 76ers win.
Jaylen Brown Addresses His Celtics Exit
Brown did not use his introduction to launch a sustained attack against his former organization. He nevertheless made it apparent that he did not appreciate every part of the process that led to his departure.
Asked about the trade cycle, Brown described aspects of it as “disrespectful” before declining to provide additional details. He also said learning he had been traded was so jarring that he threw his phone across the room.
That reaction was understandable considering Brown’s place in recent Celtics history.
Boston selected him with the No. 3 pick in the 2016 NBA draft. He developed into a five-time All-Star, helped the franchise reach two NBA Finals and earned Finals MVP honors during its 2024 championship run. He then carried an increased offensive burden while Tatum recovered from the Achilles injury he suffered during the 2025 playoffs, posting career highs of 28.7 points, 6.9 rebounds and 5.1 assists per game in 2025-26.
Despite the difficult ending, Brown characterized his Boston tenure as a completed and fulfilling chapter. He called it a “perfect cycle” and expressed appreciation for what he experienced with the Celtics.
Brown Discusses His Relationship With Jayson Tatum
Brown also addressed one of the central questions created by the trade: where things stand between him and Tatum.
The two former teammates had not spoken since the deal as of Brown’s introduction, according to his comments. Brown nonetheless emphasized that he still respects Tatum and did not portray the lack of communication as evidence of a permanent fracture.
Their relationship was scrutinized throughout their time together, particularly when Boston fell short in the postseason. Ultimately, however, Brown and Tatum answered the most important question by leading the Celtics to a championship.
Trading Brown did more than separate that partnership. Boston sent him to the team that eliminated the Celtics in seven games during the opening round of the 2026 playoffs. Philadelphia can now pair Brown with Joel Embiid, Tyrese Maxey and LeBron James as it pursues its first championship since 1983.
That is what gives Simmons’ response more weight than an ordinary social-media reaction. Brown did not simply leave Boston. He joined a direct conference competitor with enough talent to make the Celtics regret the decision quickly.
The trade’s final judgment will depend on George’s health and production, what Boston ultimately does with the acquired draft capital and how far Brown helps Philadelphia advance. On the day Brown first held up his new uniform, however, Simmons needed only three words to describe how the moment felt.
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