Celtics in Crisis: This Wild NBA Draft Night Trade Scenario Could Fix Boston After Jayson Tatum Injury

It was as if the 1993 Chicago Bulls lost Michael Jordan.

It was as if the 1986 Boston Celtics lost Larry Bird.

It was as if the 1968 Los Angeles lost Elgin Baylor.

It was Jayson Tatum’s torn Achillies, a devastating injury that might derail the Boston Celtics for years to come.

Blowing It Up In Beantown?

With Tatum on the shelf until at least the latter half of the 2025-26 season—at least—the Boston Celtics are at a crossroads.

Do they look to their current core of Jaylen Brown, Jrue Holiday, and Derrick White to keep them afloat until Taco Jay returns to form? Or do they wipe the slate clean, get younger, and hope/pray that Tatum rediscovers his Tatum-y self and can drag a young squad to the top of the Eastern Conference?

At this point, thanks to money and age, the latter option seems to make the most sense.

Brown’s salary cap-killing supermax deal is on the books until after the 2028-29 season, at which point he’ll be 33-years-old.

White is signed through 2027-28, with a player option for 2028-29, at which point he’ll be 34.

And Holiday—who’s currently 35—is in the same situation as White: On the ledger through ‘27-‘28, player option in ‘28-’29.

This leaves the Celtics with little wiggle room, so if Tatum isn’t Tatum, they might find themselves stuck on the NBA’s dreaded treadmill of mediocrity, something that Chicago Bulls fans (like me) can attest isn’t a place you want to be.

But there might be a way out.

What Can Brown Do For Them?

Any game-changing deal that comes out of Boston will need to include Jaylen Brown, and there are plenty of teams who would be way interested in taking on the four-time All-Star, among the most logical being—wait for it, wait for it—the San Antonio Spurs.

Teaming Brown with Victor Wembanyama would make the 2025-26 Spurs Western Conference contenders, and put the 2026-27 Spurs in the championship mix.

And the trade could look a little something like this:

San Antonio Spurs receive

Jaylen Brown

Boston Celtics receive

Stephon Castle

Devin Vassell

2025 first-round pick (2)

2026 first-round pick (top-10 protected)

There might need to be some pieces shuffled around—or the addition of a third team—to get the deal to work under the salary cap, but this is a good start.

For the Spurs, they land an All-Star in his prime while keeping their second first-rounder in this year’s draft (14). Teaming Brown with Wemby gives San Antonio one of the scariest duos in the West, a twosome that could someday hang with, say, OKC’s Shai Gilgeous-Alexander and Jalen Williams. Sure, losing Castle and Vassell kills their backcourt depth, but that can be addressed in the draft and free agency.

As for the Celtics, not only will they jumpstart a fine youth movement, but the acquisition of a solid backcourt duo gives them the flexibility to deal away White and Holiday, and possibly land them a second lottery pick.

If the C’s walk away from Draft Night with a pair of top-ten prospects, a young and potentially electric backcourt, and a future first, well, suffice it to say that Jayson Tatum will be thrilled when he returns ot the court.