Back in May 2024, Stephen A. Smith cited an anonymous “NBA source” claiming a Boston star’s marketability was being held back by an “I-am-better-than-you attitude.” That set off a beef between Smith and Jaylen Brown. Two years and a title later, the same tension showed up again on Smith’s own show, only this time it read less like criticism and more like genuine worry about where Brown goes from here.

On The Stephen A. Smith Show, Michael Wilbon, a commentator for ESPN, expressed real worry about how Brown’s straightforward nature will be received in his new market.

“I worry about Jaylen in Philadelphia. Philadelphia is the toughest place to play in America. It is, to me,” Wilbon said. “I worry about him because he’s got depth of thought. And people can disagree with him, as you know. You can go back and forth with him. He’s not going to sit on the side and say, I don’t want to get involved in that because it’s not sports.”

“I worry that there’s different, when they say different races for different horses, I worry about that in that, can he be the person he’s been and enjoys being there without a lot of pushback, without a lot of noise? … I applaud that about him. And also, it has consequences,” he added.

Wilbon’s comments can be backed by context.

In 2019, Brown became the youngest vice president in NBPA history, and has held the post since, speaking at Harvard and MIT along the way. In 2020, he drove through the night from Boston to Atlanta to lead a protest after George Floyd’s death, then spent that summer pushing the league to do more on social justice. So, like Wilbon said, just because something isn’t about sports doesn’t mean Brown stays quiet.

In 2024, he got left off Team USA’s Olympic roster right after winning Finals MVP, and he said outright that he thought his public criticism of Nike, USA Basketball’s apparel partner, had something to do with it, a claim Grant Hill has denied more than once, most recently three weeks ago.

That same year, Brown turned down a reported $50 million Nike deal and started his own brand, 741, because he didn’t want a standard endorsement contract that let sponsors bail if he said something they didn’t like.

Then, earlier this summer, Brown called his last season in Boston his “favorite year” despite the early playoff exit. Smith went after the comment on air, and Brown clapped back on Twitch, telling him to retire, calling him “the face of clickbait media,” and accusing him of “pushing a weak narrative.”

Hours after the Philadelphia trade was reported on July 2, Smith revisited the whole saga on his own show, Straight Shooter, telling viewers plainly that Brown is “not liked.”

Now, Wilbon has called Philadelphia one of the few “real” sports cities in America, the kind of place that ran Ben Simmons out of town. It is clear that the intense culture holds athletes to an uncompromising standard. And Brown now enters that market on a $304 million supermax contract, expected to share the ball with LeBron James, Joel Embiid and Tyrese Maxey, a roster with plenty of egos to sort out before a single word gets said to a microphone.

However, Brown, for his part, doesn’t sound rattled. At his introductory press conference, he framed the move as a fresh start: “I want to earn everybody’s respect and trust, which takes time.”

Whether Philadelphia grants him that time, or reacts to his candor the way it has with plenty of stars before him, is the question Wilbon was really asking.