‘Risk’ label slapped on heavily rumored Boston Celtics blockbuster

Teaming up Damian Lillard and Jayson Tatum on the Boston Celtics, while sending Jaylen Brown to the Trail Blazers, sounds better in theory than in actuality — this, at least, according to Boston.com’s Conor Ryan. Even after a Lillard for Brown swap, Ryan writes, the Celtics will be no closer to adding meaningful pieces via free agency and without more changes to the roster.

“Even though Lillard offers plenty of intrigue in terms of his lofty resume and standing as a sharpshooting point guard, there is plenty of risk involved with (a Brown/Lillard swap),” Ryan wrote. “Lillard’s skillset could complement both Tatum and the Celtics as a whole, but Boston will still likely be in a cap crunch if it ever managed to pull off such a trade.”

Lillard had his best season in the NBA thus far in 2022-23, averaging a career-high in points (32.2) on a career-high shot attempts per game (20.7). He will be 33 by the time next season starts, though, and arguably has a higher ceiling as a playmaker than Brown ever will. Still, it’s unknown what kind of fit there’d be with Tatum and Lillard, the former of whom didn’t thrive with a ball-dominant guard and the latter who has never played outside of Portland.

Boston Celtics analyst’s alternative Jaylen Brown to Portland proposal

The Ringer’s Kevin O’Connor offered an alternative non-Lillard trade package for Brown that would give the Boston Celtics Anfernee Simons and the 2023 NBA draft’s No. 3 pick. Should the Cs find a wing capable of filling out minutes at both forward spots — Brandon Miller out of Alabama comes to mind as someone who can be available –, this deal would benefit the team’s backcourt. A subsequent Marcus Smart/Malcolm Brogdon trade would make sense at that point.

But if the team were to instead pursue the NBA G League’s Scoot Henderson or Overtime Elite’s Ausar Thompson, there’d be an even bigger backcourt conundrum than what already exists between Smart, Brogdon, Derrick White, and Payton Pritchard.

Ideally, Brown signs a Supermax and tries to make things work in Boston. But a trade request could yield intriguing pathways with Portland.