The 2 very different routes Jaylen Brown and Boston could take this season

Here are Jaylen Brown's NBA record setting contract extension numbers:

  • 2024/25: $52,368,085
  • 2025/26: $56,557,532
  • 2026/27: $60,746,979
  • 2027/28: $64,936,425
  • 2028/29: $69,125,872
  • Typically when you ink someone to the richest contract in NBA history you want them to be a #1 guy on a potential championship team and/or a MVP candidate. When you sign non MVP/#1 guys like Bradley Beal or Mike Conley Jr. to these deals they end up becoming regrettable. The hope here is that Jaylen Brown will make a leap in this coming season 8 into a superstar player, a perennial All-Star and All-NBA player. Even if he doesn't, but he's good enough to be the second best player on a 2023-24 Boston Celtics championship team, it will be all smiles in Celtics nation next summer prior to his extension kicking in.

    Make no mistake though there are two very precise and different routes things can go in a year's time. The first is the Jayson Tatum and Jaylen Brown finally have their championship winning moment in their upcoming seventh season together. Similar to Giannis and Middleton or Jokic and Murray after several years together. This would make everyone happy and you wouldn't hear anyone complaining about Jaylen's $70 million price tag years down the road.

    Unless you're simply a Jaylen Brown fan boy, super young, or an extreme green teamer, Celtics fans know that's it's all about NBA championship banners and not just conference finals ones or even appearances. When Brad Stevens took over in 2021, he decided to stick with the star wing duo of Tatum and Brown and give them some more time, but if they remain ringless three years later, the proof will be more or less there.

    There is the possibility that Jaylen has a tremendous 2023-24 playoffs, but the Celtics still don't win due to either multiple serious injuries or Jayson Tatum stinking up a playoff series and getting eliminated that way. In that case in term of Brown, his contract, his future, and his relationship with Boston and its fans, there would still be a positive vibe around his upcoming extension next season.

    But if the Celtics don't win the title this coming season and it's a situation where Jaylen didn't excel in the eliminating series, things will unfortunately turn ugly quickly for Brown in Boston. I never get on a player due to their contract; who here has ever asked to be paid less than what they are offered? Effort or bad attitude are the only things that make me want a player gone. That said, most fans unleash on the overpaid players when their team starts losing.

    Sadly that happened to both Gordon Hayward and Kemba Walker post injuries when they were nowhere near the talent of their max contracts. And Jaylen has a super-max contract with the label of NBA highest paid. Add in the facts that Jaylen has been critical of Boston fans and people of the city on numerous occasions and tends to be rather sensitive and thin skinned to any criticism and I fear things would go south quickly if the Celtics get eliminated next season.

    I mean Jaylen is still salty that Boston fans didn't cheer his #3 selection back in 2016, presumably preferring to have traded the pick in a deal with Chicago for Jimmy Butler. Despite getting showered by love on social media, Jaylen has been critical of the very small percentage of fans that ever criticized him or dared to be open to trading him for a MVP like Kevin Durant.

    And all of the trade talk back then was about trying to get better as a team. It was never about Jaylen's contract, which was team friendly. Trust me, I've seen it with all Boston sports teams and pretty much all fan bases, the players who are overpaid get way more criticism and calls to be traded. Heavy is the head that wears the crown, and in this case the crown is a $304 million league leading contract.

    Brown said all the right things in his presser today, but will he all of a sudden become less sensitive to criticism moving forward? It's hard to change one's brain wiring. And also, Boston has the dichotomy of being one of the most progressive/liberal cities that has an NBA team, but has the stench of racism attached to their city. And truth be told, while I see much less racism and especially racist language in the city than I did in the 1980's or 90's, there are still some bad apples. And to the media, it doesn't matter if it is just one racist moron that says something. It will become an issue.

    If the Celtics lose and Jaylen plays poorly no one can guarantee that some jerk will take his vitriol way over the line and then say something racist. Or at a minimum someone will do something like they did with Kyrie and throw something like a cup at him and the narrative will be that fans are hating on Brown due to racism. Hopefully this won't happen, but until you have a city of zero racists (which I don't believe exists), it's always a possibility.

    The main point is if the Celtics don't win next season, fans will be much more vocally saying they want Jaylen traded and by then the excuses will have run out on the Tatum/Brown duo so Brad Stevens will have to pull the trigger on a trade. But here comes the rub. Jaylen Brown could have been traded a year or two ago for a king's ransom. Something like Ainge got for Gobert or Mitchell. He was younger, on a much better contract, and you still had the hope he would get even better in 2022-23 and 2023-24. If he struggles in the playoffs again next season, you'd be trying to trade a player now in his late 20's and on a $61 million a year deal.

    It would be similar to the Wizards with Beal this summer who one year after his All-NBA birth they traded for basically nothing mainly due to his $50 million a year deal with still four more seasons on it. Except Jaylen would be considerably more. Yes I know Beal had a no-trade clause, but in today's NBA all star players have defacto no trade clauses. Nets couldn't just trade Durant anywhere, nor can the Blazers trade Lillard nor the 76ers trade Harden anywhere. The Wizards under new ownership were just too scared about getting stuck paying Beal's deal that they gave in trading him too soon. They should have played hard ball and demanded that Beal add a few more teams to his list. There's no way Beal was just going to sit out the season, and if he did you could fine him.

    While green teamers foolishly called anyone that dared say the'd offer Jaylen closer to $265 million and if that wasn't good enough they'd explore trading him this summer, the most played out insult "haters," the fact is we should all be so luck to have the hate we receive be being given $265 million. Knowledgeable fans knew that as long as the team you traded Jaylen to this offseason he was at least open to re-signing with, you'd could get much more for him this offseason than you could in 365 days when he's eligible to be traded next.

    His new team would still be able to pay Jaylen more than anyone in free agency, but it would be for the much more manageable regular max. Jaylen's trade value was much higher last summer than it was this offseason, but unless he take a major leap and/or the Celtics win the championship this coming year, his value will be much lower next offseason.

    So while maybe you could have trade Jaylen for a Scoot Henderson and Sharpe from Portland or some combination of Houston young studs AND then added Bradley Beal as a less expensive costar to Tatum, since Washington was giving him away, if you scared you were "taking a step back," now we're in championship or bust mode.

    If Boston wins the title next season, there would be no reason to trade Jaylen anyway, but there's no way you're getting as good a package as the two ones I just mentioned. And there is no Jayson Tatum good friend like Bradley Beal to trade for nothing either. Please get it out of your head if you're one of those fans that think multiple 2nd rounders can now get you a star. 10 second rounders still have less value that a late lottery pick. The Beal trade was a salary dumping outlier. Multiple 2nd round picks can be used with TPE's to get you Evan Fournier or Mike Muscala types. Five of them might even get you a Gary Payton Jr or Sadiiq Bey type. Or maybe help you move up into the 20's of the NBA draft first round.

    But if the Celtics don't win next season and Jaylen is traded the return will be much worse than fans who wanted to give Jaylen the supermax this summer could even dream of. Then you have Tatum as your only star and you hope you can get lucky developing some draft pick or raw player you got back for Jaylen. Part of the reason I was hesitant to trade Jaylen for an older star like Durant was KD's higher contract. Crazy that Jaylen will soon be making more. Grant Williams was the first casualty to having to plan for two supermax players. There will be more. I personally preferred a young player like Haliburon before he was traded to Indiana and broke out. Back then you could have gotten Halliburton and probably the Kings' #4 pick for Jaylen. Now Indiana would hang up the phone if Stevens offered Jaylen for him straight up.

    So I'm hoping that Jaylen Brown spends the rest of the summer in the gym and the Celtics win banner 18 this coming season. Not just because I'm a diehard Celtics fan who wants the team to win another banner, but because I'm well aware of what the alternative would be next offseason. It would be ugly from many fans and set the team back due to the poor trade return. Wyc and Stevens are betting on #18 this coming year. It's an all-in bet on their part.