Celtics' Hot Streak Complicates Major Roster Decision Before Trade Deadline

The Celtics' unexpectedly strong start has complicated what was supposed to be a straightforward path toward financial cleanup at the trade deadline.

The Boston Celtics weren’t supposed to be here-not this quickly, not with this group, and certainly not with the financial handcuffs they slapped on themselves over the summer. But 21 games in, they’re sitting three games over .500, fresh off a statement win over the Knicks, and playing with a swagger that’s catching people off guard.

Let’s rewind to the offseason. Boston made some tough calls-financially driven ones.

Jrue Holiday, Kristaps Porzingis, Al Horford, Luke Kornet, and Georges Niang were all let go, casualties of the Celtics’ attempt to duck under the NBA’s second-apron threshold. It was a clear message: this was going to be a year to reset the books, not chase banners.

Then came the gut punch-Jayson Tatum’s Achilles tear. With their franchise cornerstone sidelined, expectations plummeted.

Some fans even started whispering the “T” word-tanking. Others wondered if Boston might trim another $12 million in salary just to avoid the luxury tax altogether.

A “gap year” felt inevitable.

But here we are. The Celtics have flipped that narrative on its head.

They’re not just surviving-they’re thriving. And they’re doing it with a group that wasn’t supposed to be this good, this fast.

“It’s only been 20 games, and there has been a huge amount of growth, from a lot of guys,” Jaylen Brown said after Tuesday’s win. “Neemi[as Queta], Jordan [Walsh], Josh [Minott], Baylor [Scheierman], Payton [Pritchard].

We’re continuing to take it one step at a time. The best is yet to come.

We’ve still got a lot of work to do.”

That’s not just lip service. This team is showing real chemistry, real development, and-maybe most importantly-real joy. The kind of joy that’s hard to manufacture, especially in a season that was supposed to be more about spreadsheets than scoreboards.

But with success comes complication. Boston is now staring down a financial crossroads, and the options aren’t exactly clean-cut.

Let’s talk about Anfernee Simons. On paper, he’s the most obvious trade candidate if Boston wants to get under the luxury tax.

His $27 million salary sticks out like a sore thumb, especially given his uneven fit off the bench. He hasn’t quite found his rhythm in this system, and while the shot-making is still there, the overall impact hasn’t matched the price tag.

That said, it’s not like Simons is dead weight. He’s a microwave scorer who can stretch the floor, and if he settles into his role, he could become a real weapon for the second unit.

The problem? There’s not exactly a line of teams eager to take on his contract.

If Boston wants to move him, they might have to sweeten the deal with draft capital-never an easy pill to swallow for a team trying to build sustainably.

Then there’s Sam Hauser. His name has popped up in some tax-saving scenarios, but let’s be clear: moving Hauser just to save money would be a tough sell.

He’s on a team-friendly deal, he’s been a key contributor on past deep playoff runs, and he’s taken real strides defensively this year. Trading him for the sake of avoiding the tax would hurt-not just on the court, but in the locker room too.

This is where the Celtics find themselves: caught between a promising present and a financially responsible future. Ownership has a chance to reset the tax clock, potentially avoiding the dreaded repeater tax down the line. But doing so could mean sacrificing pieces that are helping this team overachieve right now.

It’s a classic NBA dilemma-win now or plan for later. And in Boston’s case, the answer might not be so simple.

This was supposed to be the year they took a step back. Instead, they’ve stumbled into something that feels real.

Something that’s worth protecting.

So what do you do? Do you stay the course and see how far this group can go? Or do you make the hard financial decisions, knowing it might cost you momentum in the short term?

There’s no easy answer. Just a team that’s playing too well to ignore, a fanbase that’s starting to believe again, and a front office with some very real decisions to make.

It’s a financial puzzle. A basketball story. And right now, it’s one of the most intriguing subplots in the league.