Updated Damian Lillard trade proposal would give Boston Celtics a true Big Five

There’ve been many a Damian Lillard trade proposals involving the Boston Celtics, but the latest from NBA Analysis Network would keep all of the projected starters ahead of the 2023-24 season and add the seven-time All-NBA point guard — creating a Big Five starting lineup of Lillard, Derrick White, Jaylen Brown, Jayson Tatum, and Kristaps Porzingis. The full offer would see the Cs land Lillard for Malcolm Brogdon, Robert Williams III, Payton Pritchard, Oshae Brissett, a 2024 First-Round Pick (Top 4 Protected – GSW via BOS), a 2026 First-Round Pick (via BOS), and a 2030 First-Round Pick (via BOS).

NBA Analysis Network’s James Piercey believes that the Celtics should appeal to Lillard if he actually wants to win an NBA Championship at this stage of his career; considering most of the rumors so far have revolved around the 33-year-old heading to the Miami Heat for whatever coveted assets they can offer outside of Jimmy Butler and Bam Adebayo.

“Well, here’s the question: what’s most important to Lillard? IS he craving South Beach’s weather and nightlife? Or, is Lillard in hot pursuit of an NBA championship? If it’s the latter, the Celtics ought to appeal to him,” Piercey wrote. “We suspect that it’s the latter. So, why not Boston? Lillard would be joining forces with Tatum and Jaylen Brown. This would be one of the most talented teams in the NBA. Meanwhile, if feeling needed is a priority for Lillard, he should be happy to land in Boston.”

Lack of Trail Blazers leverage could lead to Boston Celtics, or another team, getting Damian Lillard for cheap

Lillard has wiped away any leverage the Portland Trail Blazers had in the sweepstakes for his talents with his insistence to only play for the Heat. His attitude has shifted the narrative of who he is: formerly a loyal team-first player, but now someone who needs things to go exactly his way or he won’t acquiesce.

That could help a team like the Boston Celtics swoop in and get him without losing any essential win-now pieces. Malcolm Brogdon’s injury history/post-non-Los Angeles Clippers trade reaction, Robert Williams III’s similarly spotty health, and Payton Pritchard’s unhappiness all make them non-essential in the grand scheme; particularly with a starting five filled with stars like the Jays, with more growth White, and if his output resembles his 2022-23 Washington Wizards efforts, Porzingis.