Some Celtics fan just really can't seem to wrap their minds around the fact that the Celtics re-signing a guy who just made all-nba 2nd team is a good thing.
Its not a question of whether Brown is worth the deal. Maybe he will be, maybe he won't be. The question is whether he's worth more under contract for five years or as an expiring. Then EVEN IF you answer "as an expiring" you also have to make a deal that brings back something that helps you win THIS YEAR, because they were never in a million years trading Brown for some rookie or a bunch of draft picks that would kill their chances next year.
Every team in the league would have offered Brown a 30% max if they could, the difference between that and a 35% max is about 7 million a year. So he is, at most, 7 million a year overpaid. A team trying to win a title should be fine with that. The contract runs through his age 32 season, so the its not like he's going to age into being a bad contract. He plays the most valuable position in the league. The contract is fine providing he doesn't suffer a catastrophic injury.
It's hard for the human brain to evaluate things in the context of opportunity costs. It's much easier to make a judgment about whether player X is worth $Y dollars, and it's usually an arbitrary thing. Like, 10 years ago people probably thought offering $20m to a player was crazy, because the cap was $53m, and because Larry Bird made $7m in 1991 which was the highest salary at that point. Because of cap inflation, salaries have gone up as well. So now thinking about someone who's not a top 5 player making $50m, well there's no way he's worth that, Larry Bird, Jordan etc. not to mention more recent players like Duncan, Dirk, never made that. But it's proportional to the cap, and it's relative to what their market rate is, and it's what the best choice you have in trying to retain a top player - a) let him walk away end of his contract because you don't think he's worth it; b) lowball the offer to what you think he's worth and risk him walking away after; or c) offer him the market rate, or the rate that you will keep him, and retain control over him for the next 5 years as a fungible asset that can then be traded later on.
And because we have his Bird rights is the only reason we can go over the cap to retain him - if we don't do so, given we're already over the cap, even if he walks we would still be over the cap, and we can't find another $30m player out there to replace his salary because we can't sign anyone when we are already over the cap. Do we really think there will be no takers for Jaylen at a supermax if we wanted to get rid of him? Signing him was for financial reasons as much as anything. I just don't see a path where we could have not signed him to a supermax and remained competitive. That would 100% have been a rebuild. And it's also why these top rookies like Scoot, etc. probably won't get traded anywhere, because they will in all likelihood outperform their rookie scale contract. And with Jaylen being a flight risk after this season if we had traded him before his contract expired that would be a huge risk for Portland to end up losing both their promising young guys and Jaylen, and Dame, in the space of a couple of years. I don't know why Portland would do it.
All that said, I can understand the premise that it's better to have promising young players who are getting paid sub-$10m instead of multiple max or supermax contracts, so that you can have more quality players to sign without pushing into the second apron. The caveat being that Jaylen is getting paid a supermax because he has earned the right to be paid one, after years of performing in the league. Simons is in the position Jaylen was when he signed his last contract 4 years ago. If he maintains a similar trajectory to Jaylen he will get paid in 4 years and take up 30% of the cap most likely. In a way their Simons and Scoot are our Jays 4 or 5 years ago. We would be basically saying "well the Jays didn't work out and now they cost too much, let's replace with Scoot and Simons and see if we can win something before we have to pay them maxes." In an ideal world you would keep trading these guys for fresh young blood just before they cost a lot, Belichick style, but you have to get the timing right and they have to be mature and ready to win a chip at the ages that our Jays were 4 years ago in 2018-19