Jaylen Brown is eligible for a five-year, $295 million supermax contract extension this offseason, and according to Stephen A. Smith, the Boston Celtics must think long and hard before backing up the Brinks truck.

Brown is coming off an inconsistent postseason, capped by a terrible performance in Boston’s Game 7 loss to the Miami Heat in the Eastern Conference finals, and Smith believes the Celtics should consider trading the two-time All-Star while building around Jayson Tatum.

One potential target in a swap involving Brown: Damian Lillard of the Portland Trail Blazers.

“First of all, I don’t think you give (Brown) that much, period, because he’s not your No. 1 option. That kind of money is reserved for No. 1, the No. 1 guy,” Smith said earlier this week on ESPN’s “Get Up” in wake of the Celtics’ season-ending defeat. “Well, excuse me, there’s a guy by the name of Damian Lillard in Portland. I wouldn’t mind getting somebody like him, who’s a closer, by the way, who’s a point guard as a closer, who’s a sniper. We’ve got all of that stuff going for ourselves if you’re Damian Lillard. Obviously, he’s older than Jaylen Brown, but Jaylen Brown, I think the real challenge is that he has aspirations for being that No. 1 guy and that is never going to happen with Jayson Tatum. So, the question is can he accept being 1A? And I think we’ve seen enough evidence over the course of the last couple of years where we see that’s at least a challenge for him.”

Story continues below advertisement

In a vacuum, it’s almost incomprehensible that an NBA franchise would break up a superstar tandem while both players are firmly in their primes (and perhaps still getting better). Tatum, a four-time All-Star and two-time All-NBA, is 25 years old. Brown, a two-time All-Star who just earned his first All-NBA selection, is 26. There’s a strong case to be made for Boston building around the duo despite again falling short of a championship.

But let’s face it, the Celtics haven’t been able to get over the hump. And for as talented as Brown is, he’s also crumbled in some big moments. Throwing a whole bunch of money at him — and tying up so much of the payroll in two players — is risky in itself, especially given the tax implications. The Celtics might be best served capitalizing on Brown’s trade value and shaking up their core, however wild it might seem at a surface level.

“Either you get an abundance of players, which I don’t think is necessary, or you get a superstar-caliber sniper like Damian Lillard to come to Boston in return for (Brown’s) services,” Smith said. “If I’m the Boston Celtics, I’m looking at something along those lines rather than giving him $59 million, which is more than Damian Lillard is making at this moment in time.”

Story continues below advertisement

Lillard, a seven-time All-Star, will turn 33 this summer. And he, too, makes a boatload of cash, with a base salary north of $45 million for the 2023-24 campaign. But the Celtics need to at least consider shuffling the deck, in which case Lillard obviously would be a fascinating option.

Featured image via David Butler II/USA TODAY Sports Images