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Why waiting to trade Jaylen Brown wouldn't guarantee a better return

Jaylen Brown just had the best season of his career, and the Celtics opened up a bidding war for his services. The NBA showed exactly what they thought of him, and there's no reason to believe his value would have ever gone up.
Oct 26, 2025; Detroit, Michigan, USA;  Boston Celtics guard Jaylen Brown (7) reacts in the second half against the Detroit Pistons at Little Caesars Arena. Mandatory Credit: Rick Osentoski-Imagn Images
Oct 26, 2025; Detroit, Michigan, USA; Boston Celtics guard Jaylen Brown (7) reacts in the second half against the Detroit Pistons at Little Caesars Arena. Mandatory Credit: Rick Osentoski-Imagn Images | IMAGN IMAGES via Reuters Connect

A popular trope in the media right now is this idea that the Celtics were acting rashly and that if this was the best return they could get for Jaylen Brown, they should have simply waited to deal him. But in reality, we have no way of knowing there’s any truth at all behind that theory.

Here’s what we do know: the Celtics were in trade talks for Giannis Antetokounmpo, and when that fell through, they started canvassing the league, trying to find a trade for Brown. Reports indicate they were speaking to roughly half the teams in the league and that their asking price was simply too high.

The teams that we hoped would get involved obviously weren’t interested, and many of them moved on to other deals. The Raptors pivoted to Kawhi Leonard, the Blazers took their big swing on Ja Morant, the Timberwolves went all-in on LaMelo Ball, and on and on.

Every team in the NBA knew Brown was available

This wasn’t a case of Luka Doncic being dealt in the dead of night without most teams ever knowing that he was available. This was essentially an open auction with every team in the NBA able to get involved. And the teams just didn’t want Brown. The combination of his contract and the Boston asking price was too much.

Teams either made other deals or were never really interested to begin with. Those that appeared to have interest were dropping like flies, so when Brad Stevens and company finally got a deal they liked from Philadelphia, they decided to take it before that option disappeared as well.

Sure, maybe there is a world where a month from now, a team would have gotten desperate and pushed in a few more chips for Brown, but that’s no guarantee. There’s also no way of knowing if the Celtics would have ever had the chance to recoup four draft picks, including an unprotected first from the 76ers and a juicy 2028 swap that will likely come from the Clippers.

Those are premium assets that nobody else was offering. On top of that, they got a player in Paul George, who is certainly overpaid, but is also a very good player and a good fit on the team. Just given the size of JB's contract, the Celtics were going to have to take back a lot of money, and a lot of the options, like Jerami Grant, Jordan Poole, and Brandon Ingram, were worse players on lower, but less valuable contracts than George's. In other words, they were going to have to take on some iffy contract(s) regardless, so at least they got a good player.

No reason to think Jaylen Brown's value will ever be higher

You have to remember that all draft picks aren’t created equal and consider that when thinking about sheer pick volume. Would three first-round picks have made the deal sound better? Probably. But would three late firsts from a team that would be very good after adding Brown be better than this ‘28 Clippers pick that seems destined for the lottery? I think not.

We’ve seen a flurry of deals in recent weeks, and most teams seem close to finishing their business for the summer. The Celtics wanted to be in that camp, and trading Brown was a big part of that. By waiting, they not only risk losing more suitors, but they also risk the idea of JB getting upset and making this situation uncomfortable and possibly even untenable. I don’t see any world where that would have helped Boston’s leverage.

It’s easy to sit here on the outside and judge the situation, saying the Celtics should have just waited until the perfect trade came along. But that’s just not how this works. The league, to an extent, has soured on Brown and his contract, and considering he just had the best season of his career and wants a huge extension in October, it’s silly to think his market will ever be better than it is and that the Celtics would have gotten a better deal. Sometimes, the truth hurts.

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