One failed blockbuster may have changed the Celtics’ entire offseason direction. The team entered the summer chasing Giannis Antetokounmpo, hoping to extend its championship window around Jayson Tatum. It collapsed after the Miami Heat spoiled the party. Now, insider Brian Windhorst believes the Celtics have pivoted toward a different strategy. The one that makes Jaylen Brown’s future with the franchise increasingly uncertain. 

“I guess it’s not impossible that Jaylen Brown and the Celtics could get back together, but I think that’s highly unlikely,” Windhorst said, speaking on The Rich Eisen Show.

Now, with the Giannis trade slipping past the Celtics’ grasp, Windy described how aggressively the C’s have explored JB’s market. 

“They’re offering him everywhere, Rich. I mean, I’m not in the Celtics’ offices, so I can’t say for sure, but I’ve heard the Celtics are attached to- I’m not even going to put a number on it because then I have to defend that number- many, many teams.”

Setting up the stage, the ESPN insider showed a glimpse of how the Celtics’ vision has changed in a matter of a few days. 

“The actions were that the Celtics were trying to get Giannis. If you’re trying to trade Jaylen Brown for Giannis Antetokounmpo, you are intending to try to win the championship this year, which is not a surprise,” Windy said. “The Celtics have been trying to win a championship every year for most of the last decade.”

The latest conversation, however, tells a different story. They don’t seem to want a superstar now, but draft capital.

“I have been told they’ve been asking for three, four, five first-round picks for Jaylen Brown, which leads me to believe that they’re examining a short-term future where they’re not trying to win a championship.”

That detail stood out the most, leaving Windy with two important observations. 

1. “They’re very motivated to trade him (Jaylen Brown).”
2. “They’re a little bit outside their plan, because again, their plan seems to have changed.”

Trading an All-NBA player for another superstar signals a franchise trying to maximize its championship window. But trading the same player primarily for draft picks points toward a long-term vision. 

In short, they’re moving away from a win-now vision to building a team from scratch around Tatum.

Notably, the shift also aligns with the C’s financial reality. The team has spent the past two seasons operating around the NBA’s restrictive second-apron threshold. Brad Stevens also trimmed salary by moving veterans such as Jrue Holiday, Al Horford and Kristaps Porzingis.

Even after those moves, Jaylen Brown’s projected $57 million salary, along with JT’s $58 million, remains one of the league’s largest commitments. Turning one of the contracts into draft assets would provide significant financial flexibility. It will ultimately ease the pressure created by the second-apron tax. 

To name a few, 

• Cannot trade first-round picks from seven years out.
• Cannot use trade exceptions from previous years.
• Cannot use cash in trades.
• First-round pick moves straight to the end of the first round if the team stays in the second apron for three of five years.

Wind’s comments, therefore, raise a larger question. If Boston is no longer operating strictly in win-now mode. What does that mean for the rest of the roster?

Draft picks over Jaylen Brown: the Celtics’ new vision

It creates a delicate balancing act for the Celtics. 

Jayson Tatum remains firmly in his prime. Trading Jaylen Brown for future draft picks would, in turn, lower the team’s championship ceiling at least for the next few seasons. Moreover, there is no certainty that the future draft picks would ultimately turn into a player of Brown’s caliber.

Meanwhile, Brown hasn’t suggested that he wants to leave the house.

The former Finals MVP is coming off arguably the best season of his career. He averaged 28.7 ppg, 6.9 rpg, and 5.1 apg while helping the team finish second in the East without Tatum.

Now, with the failed Giannis trade, interest around the league has continued to grow. The Denver Nuggets have emerged as one of the frontrunners to nab Brown, as per Chris Haynes. Apart from that, teams like the Raptors, Nets, and Hornets have also surfaced in reports.

Notably, the Blazers emerged as potential suitors up until the latest Ja Morant blockbuster.

Whether the Celtics’ strategy to trade out Brown results in a deal remains to be seen, but it also raises important questions about Tatum’s timeline. Asking a franchise player, who is in his prime, to wait through a draft-driven reset is a tough ask.

The Celts have two options. One is to chase the ring with the team centered around Brown and Tatum. The other is to prioritize financial flexibility and future assets to evade the tax rules.

Looking at the rumors, the second option seems to be rolling out.