Jaylen Brown is gone from Boston, and that alone has turned the Celtics’ past into a magnet for what-ifs. The latest one is a big one: what if the franchise had taken a different swing in 2016 and ended up with Kevin Durant, Jimmy Butler and Al Horford instead of the path that eventually led to Jayson Tatum and Brown?
The Brown angle matters because Boston wasn’t just willing to move him once he was in the building. The Celtics had already been open to dealing the pick that became Brown years earlier, when they explored a Butler trade with Chicago back in 2016. The Bulls wanted the Celtics to send the No. 3 pick and the Nets pick the following year - the one that became Tatum - and Boston passed.
On the surface, that’s easy to understand. Chicago’s ask was steep.
But that summer wasn’t operating in a vacuum. Boston was also chasing Durant, and the Celtics made a serious run at him before he chose Golden State, a move he still defends.
That’s where the imagination starts to run wild. Boston had Horford in hand, and Durant supposedly wanted to play with him.
If Butler had been added too, maybe Durant looks at that group differently. A core of Butler, Durant and Horford would have put the Celtics right in the title mix.
It also would have changed everything else. The Jays era might never have happened in Boston.
Brad Stevens might have stayed on the sideline instead of moving into the front office. And Miami might never have become such a problem for the Celtics if Butler had been wearing green and white instead of red and black.
Still, there’s a reason Boston never pulled the trigger. Danny Ainge’s hesitation suggests he didn’t feel sure enough that the rest of the summer was going to break the right way. Horford’s arrival that year came in part because Atlanta didn’t go beyond Boston’s offer, while Ainge’s decision to move down from No. 1 to No. 3 and ship Avery Bradley for Marcus Morris was another sign he believed Gordon Hayward was coming the next summer.
What-ifs don’t change anything. But Boston landing Durant, Butler and Horford in one summer is the kind of possibility that’s hard not to keep turning over.
In Other News...
NBA Legend Blasts Celtics Over Hard To Defend Jaylen Brown Gamble
Charles Barkley did not hold back on a recent podcast, putting the Celtics on blast for shipping Jaylen Brown to the 76ers in a move he called one of the craziest trades he has ever seen. The backlash has fit the wider reaction around the deal, with media analysts handing Boston low grades because the return centered on an aging Paul George and draft picks rather than a clear, immediate replacement for Browns impact.
Brad Stevens has defended the trade as a roster-building decision tied to the teams structure and salary cap realities, but that explanation has not quieted the questions. For a franchise that has spent so much time trying to balance present contention with future flexibility, the Brown gamble has quickly become the kind of move that invites debate long after the initial shock wears off. [Read more 🡒]
How The 76ers Managed To Pry Jaylen Brown From Boston
The Celtics longtime rivalry with Philadelphia took another twist as the 76ers finally landed Jaylen Brown in a trade built around two first-round picks, two second-round picks and Paul George. What had started as Bostons pursuit of Giannis Antetokounmpo ultimately shifted the market in a different direction, and the end result was one of the leagues biggest roster swings of the offseason.
76ers president Mike Gansey said the talks stretched over several weeks, with Philadelphia staying persistent until the deal came together. For Boston, it is another reminder of how quickly a contenders plans can change when the top of the market moves, and for the 76ers, Brown arrives with the kind of impact that could push them toward another title chase. [Read more 🡒]
Celtics Just Became The Clearest Warning About The NBAs New Rules
The NBAs new salary cap rules are already changing the way front offices think, and Boston has become one of the clearest examples of what that looks like in practice. The leagues second apron has turned roster-building into a much tighter exercise, forcing teams to balance talent, contract structure, and long-term flexibility in ways that were not nearly as pressing before.
Bostons trade of Jaylen Brown underscores how quickly those choices can become unavoidable for a contender. The Celtics are hardly alone in confronting the new reality, with teams like the Knicks, Thunder, and Pistons also working through the ripple effects, but Bostons move may end up being the one other clubs study most closely as they decide how far they can push their own payrolls. [Read more 🡒]