Brad Stevens’ genius is about to be tested.
Amidst the devastation from Jayson Tatum’s injury and disappointment in how badly Boston played against the Knicks, the biggest cause for optimism around Boston is the unwavering belief in the Celtics President of Basketball Operations ability to make smart moves.
The way the once-promising 2024-25 season ended lessened the pressure on Stevens in the short term.
If the Celtics had lived up to expectations and won their second straight NBA title, there would have been huge pressure to keep as much of the band together to attempt a three-peat.
But Tatum’s expected absence for much, if not all, of the 2025-26 season, combined with the embarrassing loss to New York, should allow Stevens to make decisions without the same fear of immediate backlash.
But the grace period won’t last long. Banner No. 19 will become a goal and then an expectation very quickly, especially with a new owner who doesn’t have a ring of his own yet.
Stevens’ challenge is tricky. Through trades, he’ll need to at least get the team’s salary commitments under the second apron for 2025-26 to avoid huge luxury tax penalties and roster restrictions in the future. At the same time, he’ll try to create a roster that is younger, but still equipped to contend when Tatum returns. That’s not an easy minefield to tiptoe through.
The Celtics’ dynastic history has been built on smart trades.
In 1956, Red Auerbach traded Ed MacCauley to the St. Louis Hawks for the No. 2 pick in the draft, which they used to draft Bill Russell. That deal led to 11 Celtics titles, while St. Louis no longer has an NBA franchise.
Auerbach struck again in 1980 when he traded the No. 1 overall pick to the Warriors, who coveted Joe Barry Carroll, for the rights to Robert Parish and a draft pick that became Kevin McHale. That led to three more Celtics titles and enshrinement for Parish and McHale, while Carroll needs to pay $25 (with a senior discount) to visit the Naismith Hall of Fame.
Danny Ainge made two huge trades in 2007 to get Ray Allen from Seattle and Kevin Garnett from Minnesota which directly led to the 2008 Championship.
Ainge then traded Paul Pierce and Garnett to Brooklyn in a 2013 deal that brought the Celtics the draft choices that led to Jaylen Brown and Tatum. That deal and Stevens’ trades to get Jrue Holiday and Kristaps Porzingis last year helped secure the 2024 title.
But those successes shouldn’t be an urgent indication to make moves. Last year’s championship was also built on Ainge’s good fortune that nobody took him on his 2015 attempt to trade four first-round picks to move up to get Justise Winslow, who was the third-leading scorer on the G-League’s Wisconsin Herd last year.
Stevens has to decide if his best path is trying to work the edges to keep this championship window open or being aggressive in hopes of opening the next window. Tatum doesn’t turn 28 until March, making him young enough to be a pillar in either plan.
Still, both are risky and require Stevens to make a lot of educated guesses.
If he tries to keep as much of the current roster intact as possible while getting under the second apron, Tatum could return to a team that isn’t good enough to contend and isn’t bad enough to draft stars. That would look a lot like what the Milwaukee Bucks are currently facing.
But if Tatum comes back in the middle of a slowly developing rebuild, that hasn’t produced new stars, the Celtics would be similarly set back.
Stevens has to guess the best answer to lots of questions, including the following big ones:
Are the Celtics counting on/hoping for Jayson Tatum to be back for any meaningful contributions in 2025-26 or not?Do they keep Derrick White? He’d be their second-best player going into next season. A team centered around Brown and White is probably enough to at least contend for a playoff spot next year. But he’ll turn 31 in July. That’s not old-old, but his skills and trade value are both likely to decline — or at least start to — by the time Tatum is back.Will Jaylen Brown still be at his peak when Tatum comes back?Can the Celtics get someone—or a package of someones—who will be better than Brown will be whenever Tatum returns?
If Stevens guesses right and leads the Celtics to Banner 19, he’ll probably be headed to the Hall of Fame.
But the difference between being a genius and a scapegoat can be just one bad move.
