re: Jaylen Brown is eligible for a 5-year, $295 million extension this summer

Honestly I think I would trade Brown to Portland for Anfernee Simons and the #3 pick then take either Scoot Henderson or Brandon Miller and be set in the backcourt for the next 7 years

with a top 8 next year of
Smart
Simons
Tatum
Horford
R Williams
Brogdon
Henderson or Miller
Gallinari/FA Big

that is once again EC Finals level squad with some flexibility. If you extend Brown, all of the flexibility goes out the window and the penalties become punitive in 2025 when they hit the repeater tax thresholds

I think stevens will extend Brown (an All NBA bird in hand) and figure the rest out on the fly