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Mailbag answers - part 1: the Jaylen Brown questions

You had a lot of questions about Jaylen Brown. I have scattered and conflicted answers.

NBA: Chicago Bulls at Boston Celtics David Butler II-USA TODAY Sports

We asked for your questions and you delivered (thank you!). There were a number of questions about Jaylen Brown and since that’s the most important topic of the offseason, I figured I’d do a dedicated post answering questions about him and his situation. Stay tuned for the next section coming soon with my answers about the rest of the roster and team.


Will Brown take less than

Will the Celtics offer more than

Jeff I’m thinking he’s going to Houston.....your thoughts

While I think this is an oversimplification, I think there’s a case to be made for a more refined decision tree thought process.

So you start with picking between the following choices:
- Retain Jaylen Brown on a SuperMax contract
- Trade Brown for some package of players and picks that represents near-equal value

If you want to retain him, you still have to find out if Jaylen Brown is interested in the Supermax. I would think so because it is the most money he can get, but he may prefer to play out his contract and become a free agent. If that is the case, then you immediately look to trade him.

If you do decide to trade him, either now or later, you have to decide if you want another star player in return or a step back in immediate talent in favor of future potential (and cost savings). See more thoughts on this below.

This is oversimplified since a lot of these issues are intertwined, but it may help to compartmentalize things rather than trying to tackle all at once a broad question like “is Jaylen Brown worth the supermax under the new CBA rules?”


Do you see Jaylen agreeing to a more team-friendly deal (one that doesn’t break the bank for team salaries, but one that still reflects his All-NBA status)? Jaylen strikes me less about making money, but more about mutual respect, which makes me believe that it’s possible. If so, what would it look like?

Technically the Celtics have the option of offering Jaylen more than the standard max and less than the SuperMax. That would still be more than any other team could pay him and in theory it would save some money that could be allocated to another player’s salary.

With that said, I don’t see the benefits outweighing the negatives. You may be able to save a few million dollars (forgive me, I don’t know the exact numbers), but you risk insulting Jaylen who already took a team-friendly deal on his last contract and out-performed it. As others have noted, he’s a Players Association VP and there’s pressure there to maximize what he gets as a precedent for other players.

The only exception would be if Jaylen Brown came to the Celtics with the idea of taking less in order to add another player. However, everyone involved would need to have a clear plan for who that added piece would be.

Bottom line is that this path seems unlikely.


Do the Celtics have enough assets to move up in the draft to get a highly touted player?

If they decide to trade Jaylen Brown, then yes. I think they could make a real bid for one of the top 2 picks in the draft (if they wanted to). If that’s the direction they want to go, I’d imagine they’d be targeting Scoot Henderson who has all the makings of an elite combo guard in the NBA. But he won’t be at Jaylen’s level in his first year or two (if ever) so the team has to weigh what they are looking for. Which brings me to...


I’m not saying they should. But if the Celtics do explore a trade with Jaylen Brown, what is a realistic package to obtain?

The Celtics are title contenders right now. You can quibble with that distinction if you like, but getting to the Finals last year and being a win away from the Finals this season indicates that they are very much in the running. If a few things break their way in either year, they could be champs.

If the team thinks that running it back with some changes outside of the core gives them another reasonable chance at competing for a championship, then they’ll do that. If they decide that they’ve reached their ceiling with this group and a change needs to be made, my assumption is that they’ll still be looking to compete for titles in the immediate future. All of which is to say that they’d probably prefer to trade Jaylen for an equal level star.

The problem is, star-for-star trades are very hard to complete. Often times the team dealing a star is looking to tear down and restart with a package of picks and prospects. Take Portland for example. The general thought is that they’ll either take the package of picks and prospects for Dame or they’ll look to build around Dame by dealing their pick and some package of players for another star. Dealing Dame for Jaylen doesn’t make much logical sense.

That said, it only takes one star to demand a change of scenery and who knows what can happen. Maybe they could work something out with Karl Anthony-Towns, LaMelo Ball, or Bradley Beal coming back (with picks and players going one way or the other to balance the trade).

If not, then you might be left taking a step back in order to take a step forward. Maybe a deal for a high draft pick and an intriguing player is the best that you can get. That might be a difficult sell to Jayson Tatum as he’s getting ready to sign his own SuperMax contract. Especially with limited time left with Al Horford on the roster. You might need to get a third team involved in order to flip those assets for a star right now.

As you can see, none of this is easy or straightforward. On one hand it feels like a Bill Belichick type decision maker would look to move someone a year early (before they become very expensive). On the other hand, we’re so close that it seems like we should largely run it back and pay Jaylen the money that he’s earned. There will always be an opportunity to trade him later (perhaps not at the same value as he’d bring this summer, but still a substantial return).

Dave Higgins

Hey Jeff. With four conference finals and one trip to the NBA finals can Boston lose Brown and still contend for the Larry O’Brien Trophy? Should any team trade an All NBA Player for a dream? Has a team ever traded an All NBA player and gotten better? I’m not talking about money. Just talent. Houston traded away Harden and have become a perennial lottery team. The Pelicans traded Anthony Davis and are still praying his replacement can be healthy for a year.

Those are good questions Dave. I think if you are in favor of trading Brown, you either need to hope another star is coming back in return, or you have to be ready to take at least a temporary step back. I’m not there yet, but I guess we’ll see.

Well, those were my somewhat scattered thoughts and answers to your Jaylen Brown questions. I’ll follow up with the rest of the answers soon. Thanks!

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