Before Banner 18 became reality, Danny Ainge nearly rewrote the Boston Celtics with a different plot. In 2018, with Kyrie Irving already in place, Boston’s architect dreamed of adding Anthony Davis and Kevin Durant to build an unstoppable superteam. The price, however, threatened to sacrifice two rising names still finding their footing. Ainge chose patience over star chasing, keeping Jayson Tatum and Jaylen Brown. Six years later, that gamble delivered what every vision ultimately chases: an NBA championship.

For years, the league treated the Brown-Tatum duo as untouchable. However, this offseason carries a very different vibe. With NBA champion and 2 time MVP Giannis Antetokounmpo emerging as Boston’s dream target, the front office faces a crossroads. Even if the Celtics miss out on the Greek Freak, league insiders believe Jaylen Brown could still see the exit door.

ESPN’s Brian Windhorst revealed on Get Up that Boston has gone “all-in” on its pursuit of Giannis Antetokounmpo. “The Celtics and the Heat are the two teams aggressively going after Giannis,” Windhorst said. “I would say they are the finalists.” More importantly for Boston’s future, he added: “They were very cautious about putting Jaylen Brown in an official, firm offer. I believe they have. Jaylen Brown is on the table, and Jaylen Brown could get traded for Giannis in the short-term future.”

Windhorst’s reporting has since been reinforced by multiple insiders. ESPN’s Shams Charania indicated a resolution could arrive before the NBA Draft, while Marc Stein reported Boston has positioned itself as one of Milwaukee’s strongest suitors, with a Jaylen Brown-centered package emerging as the foundation of its offer.

Windhorst explained that Boston’s aggressive approach stems from a harsh internal evaluation following its first-round exit. “They’ve taken a hard look in the mirror,” he said. “They think they’re not as good as the Knicks, and they believe they need to upgrade their team.” Considering New York is coming off a championship run and returns most of its core, Boston appears unwilling to stand still after surrendering a 3-1 series lead to Philadelphia.

Windhorst stopped short of reporting an imminent Brown trade elsewhere, making it clear he was offering his own interpretation of events. “I am now speculating that if Jaylen Brown doesn’t get traded for Giannis, they may trade him somewhere else,” he said.

What makes the situation surprising is Brown’s recent production. The 2024 Finals MVP delivered arguably the best season of his career in 2025-26, averaging 28.7 points, 6.9 rebounds and 5.1 assists while helping Boston secure 56 wins despite Jayson Tatum missing significant time. His importance only grew in the playoffs, where he averaged more than 25 points per game against Philadelphia and carried much of the offensive burden.

Publicly, there is little evidence of tension between Brown and the organization. When rumors surfaced that the All-Star was frustrated with his role, Celtics president Brad Stevens dismissed the speculation. “He has not expressed those frustrations to me,” Stevens said. “We’ve been here 10 years together and I love JB and everybody around here loves JB.”

If Antetokounmpo ultimately lands elsewhere, the bigger question becomes whether Boston would still consider reshaping its roster. So far, no major insider has reported that the Celtics are actively shopping Brown beyond the Giannis discussions. That possibility originates solely from Windhorst’s own speculation, making the next phase of Boston’s offseason one of the league’s biggest unknowns.

Jaylen Brown is feeling energized by the online chatters

While trade speculation continues to dominate headlines, Brown has shown little concern publicly. Throughout the season and into the offseason, the Celtics star repeatedly pushed back against criticism, whether it came from referees, analysts or fans questioning Boston’s direction.

Meanwhile, the 29-year-old called it his “favorite year” right after losing Game 7 to the Philadelphia 76ers in the first round of the playoff series. This led fans and experts like Stephen A. Smith to call him out. Thus, social media, precisely comment sections of posts related to the star forward, were filled with comments from unhappy fans. Most of them hoped not to see him again on the floor. Others pointed out that the Celtics front office will trade him because they don’t like him anymore.

Brown later explained why he viewed the season so positively despite the disappointing finish. “The expectations were for us to fail, to be nothing and to quit,” he said on stream. “We did the exact opposite. We fought every single day. We aren’t satisfied with the result, but to maneuver through that adversity and galvanize as a group, that’s why this was my favorite season.”

Addressing the matters, Jaylen Brown finally spoke up. He said, “I’m somewhat grateful because I get to see some negativity that I didn’t want, but that just gives more fuel to the fire. I get to see some comments or takes that I didn’t even care to see, but it just gives me more fuel to the fire.” JB added, “So, to all the people that’s doubting me, that want me to do this, or want me gone, or whatever, you’re turning me into a monster. I’d say it’s great character building.”

The dilemma facing Boston is not unlike several franchise-altering decisions from NBA history. The Raptors moved DeMar DeRozan to acquire Kawhi Leonard before winning a championship in 2019, while Brad Stevens himself shocked Boston fans by trading Marcus Smart for Kristaps Porzingis before the Celtics captured Banner 18. Whether Jaylen Brown becomes the next difficult sacrifice may depend entirely on what unfolds in Milwaukee over the next few days.

Well, Jaylen Brown is positive about the online backlash. But his future with the Celtics seems more bleak than ever. If the front office truly parts ways with him, where will JB go next? Moreover, will they end up with Giannis Antetokounmpo? The next 24 hours are going to be interesting!