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BOSTON — On the day the Celtics agreed to trade him, slamming the door on a beloved era in the organization’s rich history, Jaylen Brown walked through a crowd toward the court of a one-on-one basketball tournament in Orlando.

Judging by his casual stride, one never would have guessed such a drastic shift in Brown’s life and career was underway. His highly-decorated Celtics tenure, which could one day see his jersey lifted into the TD Garden rafters, was ending after 10 seasons in stunning fashion. After exploring Brown’s market for weeks, president of basketball operations Brad Stevens had decided to break up the highly successful partnership with Jayson Tatum and send the 29-year-old Brown to the Philadelphia 76ers for 36-year-old Paul George, two first-round picks and two second-round picks.

Brown, a five-time All-Star coming off his best season, had won the 2024 championship and NBA Finals MVP award in Boston. He made second team All-NBA twice, including this past season. He and the Celtics experienced some playoff failures, but with him, they were always relevant contenders. He even valued the letdowns because of how they forced him to sharpen his skills; he could be trusted to improve year after year. And he seemed to appreciate Boston, pouring himself into the community off the court while contributing to a decade of winning on it.

So how did Brown’s time with the Celtics come to such an abrupt end? How did they become so open to trading him that they continued to shop him around the NBA even after a pursuit of superstar Giannis Antetokounmpo fell short? How did they reach the point where, on Wednesday, they agreed to trade Brown for what was widely viewed as an underwhelming package?

Wearing sunglasses and a black hat, Brown slowly made his way onto the floor. Following his brother, Quenton, Brown strolled toward Hall of Famer Tracy McGrady for an embrace. Brown and McGrady have had a close friendship for years, dating back at least to 2018 when they worked out together at McGrady’s gym in Houston. Years later, they would reveal on a podcast that McGrady helped convince Brown not to request a trade from the Celtics early in his career.

In early May, McGrady shared a different message about Brown, stating on his podcast a belief that the Celtics star’s “frustrations lie deeply within the organization and other things we don’t really have details to.” Though McGrady later walked back his comments — Brown responded by saying he would stay in Boston for the next decade if it were up to him — the initial quote still raised eyebrows given their relationship.

It was one final billow of smoke from a summer of drama. Brown spent his trade day with the friend who had seemingly helped light the match.

The quality of the package the Celtics received and the timing of the deal, with three seasons left on Brown’s contract, left some around the league wondering why the team seemed to feel so much urgency to move Brown now.

Over recent weeks, the Celtics began to give other teams the impression they were seriously weighing the possibility of a future without Brown even after their trade pursuit of Antetokounmpo fizzled. Though team sources said they kept Brown in the loop throughout the whole process of trade negotiations, and that he wasn’t surprised by any of the news that became public, he took offense to the way they approached the situation. While live streaming Thursday night, Brown said he wasn’t thrilled with the amount of respect he was shown during the process.

“I definitely think there’s more to it,” Brown said, noting that Stevens is probably getting criticized. “… I just wish that the more to it could have been explained to me because if the more to it was explained, I think I would have understood. I thought I earned respect enough to get that explanation but hey, obviously, I was wrong.”

In a statement earlier Thursday, Brown thanked the city of Boston and the community he built there, but did not thank the organization.

“I’m big on respect,” Brown said in his written statement, “and actions speak louder than words.”

The Celtics believe that the four picks they received in the trade, including two second-rounders, should all be valuable whether they keep them or use them in a future trade, according to a league source, who, like others in this article, spoke on condition of anonymity to discuss private negotiations. The prize of the bunch might be a complicated 2028 first-round pick/pick swap, which could either give the Celtics a pick swap into the top half of the draft or a second pick later in the first round, depending on the outcomes of the teams involved. The other first-round pick, a 2031 selection from Philadelphia, is unprotected.

The Celtics also acquired George, a nine-time All-Star who averaged 17.3 points in 37 games last season. Though some NBA observers were left wondering if the Celtics had a subsequent move lined up, don’t expect another shoe to drop. George only has two more years left on his contract, one fewer than Brown, but a league source also said the trade was not driven by finances.

The Celtics’ actions suggested they valued Brown differently than how he valued himself. There were even signs back in February that they were considering a major move involving Brown, as league sources say they made a late push for Milwaukee’s Antetokounmpo before the trade deadline. That pursuit continued in the summer, of course, when the Heat won those sweepstakes and the Celtics were forced to face the harsh realities of Brown’s market.

In the days leading up to this week’s deal with the Sixers, it is quite telling that two of the reported suitors — Denver and Portland — had shown no interest in meeting the exorbitant asking price that Boston had previously put forth. Front office executives all around the NBA had been talking about the unreasonably high bar they’d set, how the Celtics expressed a strong desire to land as many as four first-round picks. Even teams that many assumed would eventually get involved, with the Houston Rockets among them, chose to stay on the sideline. Per league sources, the Rockets — whose head coach, Ime Udoka, had made an NBA Finals run with Brown in 2022 when he was in Boston — did not pursue Brown.

Another team with widely reported interest, the Trail Blazers, similarly did not join the chase. A Blazers team source said the Blazers were never enamored with Brown, even before Boston made it known he was available on the trade market. Two factors went into the Blazers’ disinterest: Their analytics viewed him as a negative player and the Celtics’ asking price was too high. “We were never aggressively looking to trade for him,” a team source said. “And particularly not at their price.”

The cool market suggested the existence of a significant gap between the general perception of Brown, who finished sixth in MVP voting this season, and the way he is seen within the NBA. Though the idea of him being viewed as the seventh-best player on a given team was widely mocked, a recent report that one front-office member saw Brown in that way illuminated the reality that advanced analytics never shined too brightly on Brown’s game. Even more pointedly, a current general manager, speaking anonymously to comment on internal team discussions, told The Athletic in the wake of the trade that he doesn’t view Brown as a top-50 player in the NBA.

For all of Brown’s individual accolades, the Celtics over the years consistently saw no dropoff, statistically speaking, when he left the court. Even in the Boston front office, some believed Brown’s impact did not match his reputation.

Over the years, Brown had sometimes voiced that he didn’t believe analytics could capture everything he contributed on the court. He seemed well aware that some of the numbers weren’t favorable to him long before responding to that train of thought during a recent social media flurry. Brown pointed out that nobody has won more games than he has, including playoff games, since he entered the NBA.

“Analytics nowadays (are) used to discredit and control narratives,” Brown wrote on X on June 27. “Roll the ball out none of these guys better than me on both ends…”

That sentiment about his on-court impact was not shared by everyone with the Celtics. Stevens always seemed to place a high value on Brown, making him the highest-paid player in the NBA in 2023 after arguably the most disappointing playoff series of his career. But the market seemed less sold that Brown was worthy of his current contract.

As several front office executives shared with The Athletic, the most significant suppressor to Brown’s market was his massive salary. He is owed a combined $182 million in the next three seasons, topping out at $64 million for the 2028-29 campaign (and representing 35 percent of the team’s salary cap). He is slated to be the seventh-highest paid player in the NBA next season, behind Steph Curry, Nikola Jokić, Tatum, Anthony Davis, Antetokounmpo and new teammate Joel Embiid.

In today’s NBA, where there is a serious roster-building price to be paid for surpassing the second-apron in addition to the exorbitant financial penalties, the prospect of paying more than one player that much money can be disastrous for a team’s depth. These past two finals have underscored that widely-held belief, with all four of the featured teams (Oklahoma City, Indiana, New York and San Antonio) boasting deep, versatile rosters.

So when it came to Brown’s market, it’s clear rival executives didn’t believe he was valuable enough to justify the contract. Or, more specifically, that what he brought to a team outweighed the fact his presence would make it challenging to provide top-tier supporting talent. What’s more, some rival executives said they believed Stevens was at a negotiating disadvantage because he had never truly shopped Brown to the entire league in the past. And when his asking price came in so much higher than teams cared to go, that disconnect ultimately doomed the Celtics.

As for the notion that Boston should have waited, and perhaps revisited a deal down the road if they couldn’t mend fences with Brown, the possibility of the star making a formal trade request was seen by rival executives as the sort of thing that would put more duress on the Celtics.

If the Celtics and other teams evaluated him as one of those overpaid players, it would have sharply contrasted with Brown’s self-assessment: He saw himself as the NBA’s best two-way player, as he said during the season. On top of all of his previous accolades, Brown believed he proved plenty about himself last season. Since 2022, when he and the Celtics were able to move past the team’s willingness to trade him for Kevin Durant, he had ascended in his career. It wouldn’t have been as easy for the organization to mend the relationship with Brown this time.

Based on how the Celtics operated, they seemed to understand that.

With Tatum out for most of last season, Brown took the reins — and something shifted.

“I think this has been my favorite season so far,” Brown said in December, “being able to get an opportunity to lead a group.”

He didn’t get enjoyment just because he took over as the No. 1 option with the team’s star sidelined. He loved seeing his younger teammates succeed alongside him. He took pride in the way the organization exceeded all realistic expectations after losing half of its rotation in the offseason, including three former All-Stars in Al Horford, Kristaps Porziņģis and Jrue Holiday, plus an injured All-Star in Tatum. Brown saw beauty in how quickly the Celtics jelled after going through so many changes.

“It just doesn’t happen,” Brown said late in the regular season. “I’m very proud of this group that we’ve been able to come together and find chemistry and the product looks like it looks. It could have looked completely different.”

Brown helped the Celtics succeed more than most outsiders considered possible. As they won 56 games, several of Brown’s teammates pointed to his competitiveness and leadership as primary reasons their season didn’t go sideways after the loss of so much talent and basketball IQ. His coach highlighted his leadership. Brown helped set a tone of intensity during training camp, but also stayed patient with his suddenly far less experienced team. After Boston fell to 0-3 in October, giving Brown his first three-game losing streak since March 2023, he didn’t lose his cool. Instead, as much as he thought Boston fans wouldn’t want to hear it, he stressed that the new-look group would need time to figure things out.

The Celtics proved Brown wrong on that point by quickly finding an identity. While they did it, he flourished in his new role, posting career-high averages of 28.7 points, 6.9 rebounds and 5.1 assists per game.

Only small hints of possible trouble began to emerge. As Brown consistently expressed how much he was savoring the season, what went unsaid was that the Celtics’ formula would need to change significantly again once Tatum came back, and that, after a career of accepting smaller roles than he believed he could handle, Brown could have some reservations about sliding back into one. As much as Boston thrived after Tatum returned in March, going 13-3 with him during the regular season, Brown let it be known that the adjustment wasn’t always easy for him.

“It takes humility and it takes some understanding,” Brown told reporters on March 16. “I think JT is extremely important to us for what we want to do. Obviously, I’m having a great season, but then I have to just think, what’s the big picture? And sometimes that’s not easy, but I always put the team first and what the bigger picture is first.”

Over the years, Brown had a habit of doing just that. Still, the Celtics began to have questions about whether he would remain fully bought in moving forward, according to league sources. Internally, they wondered whether they could keep everyone on the same page basketball-wise, as they had always managed to do in the past.

Some around the league believed Boston had a potential problem brewing when Brown spoke so glowingly of the experience he had last season, when Tatum was sidelined for 66 games. Not helping the external perception of the situation, Tatum’s trainer, Drew Hanlen, posted several times on social media about how well the Celtics played when the ball was in his client’s hands.

“Last night, (Tatum) had a usage rate of 39.4%,” Hanlen posted on X on March 30. “Celtics are really tough to beat when Tatum’s usage is over 33%.”

Tatum posted a usage rate of 29.2 percent after returning on March 6. Brown, who led the team at 33.2 percent during that stretch of the season, similarly topped Tatum in the category during the first round of the playoffs. Hanlen didn’t necessarily speak for Tatum, who was less than 100-percent physically and never complained about his touches, but it was the first time since Tatum’s rookie season that he finished with a lower usage rate than Brown.

With Tatum healthy again, it would have been understandable if the Celtics wanted to flip their hierarchy back to the old normal. For that to work, they would have needed Brown to take a step back after he had shown what he could do as the top option.

Jayson Tatum and Brown had a highly successful partnership on the court, including one title, but last year – with Tatum out for a large portion of the season — shifted their dynamic. (Maddie Meyer/Getty Images)

As recently as this week, the Celtics were giving indications they were still willing to bring Brown back if they didn’t find a trade they were willing to accept. If that had happened, they would have needed to confront any lingering issues about the trade negotiations. They would have also needed to make sure everyone was aligned from a basketball perspective.

Contributing to concerns about the situation, the Celtics believed that Brown went off script too often during playoff games as Boston blew a 3-1 first-round lead to Philadelphia, according to a league source. Over the final three games of that series, the Celtics were outscored by 57 points with Brown on the court. Though he scored 33 points in a Game 7 loss, he shot 12 for 27 from the field and finished the series with more turnovers than assists. Afterward, despite the loss, he stated how much he appreciated the style the Celtics played in that game, which was played without Tatum on the court. He thought they had played faster and freer.

“Tonight, I wish we played that style and trusted that style more, even throughout the playoffs, even through wins and through losses,” Brown said. “Obviously it’s not always the easiest decision, but I wish that style for our team was how we empowered the rest of our group, and you saw tonight how everybody came out and they played their tail off. I wish we trusted that more.”

Though far from unforgivable, those comments could have been viewed as a criticism of head coach Joe Mazzulla. They could have been taken as a hint that Brown preferred how the Celtics played without Tatum. Regardless of what Brown intended, as he ended the best season of his career, some around the NBA wondered whether his words suggested the possibility of future friction between him and his organization.

One week before the trade, Stevens emphasized how much the organization had always appreciated Brown.

“I think the one thing that I want to make very clear is how valued he’s always been,” Stevens said after the first round of the NBA Draft. “He’s been amazing. He’s been an amazing teammate. Great person to be around. Whether that run ends 10 years from now when he retires or before, there’s a lot to celebrate.”

Ironically, Brown might have foreshadowed the end of his Celtics tenure eight years ago.

While speaking at Harvard, he spoke about a paper he had read in college at Cal about the difference between identities players see for themselves and the identities a coach — or in this case, an organization — gives to them. Brown said friction begins when those identities clash.

“Like, if I say that I want to be a point guard and then the coach tells me I want you to just play defense, that’s it,” Brown said. “That’s when the butting of heads comes in.”

In the end, the clash in identities seemed to not necessarily be between a player and coach, but possibly between an organization and player.

– Jason Quick contributed reporting from Portland.