While the Portland Trail Blazers make aggressive moves as part of their long term plan for a post-Damian Lillard future, Eastern Conference contenders are receiving players who they think can help them win big right now. First, Portland sent Damian Lillard to Milwaukee in a three team deal, and now Portland sent Jrue Holiday--acquired from Milwaukee as part of the Lillard trade--to the Boston Celtics in exchange for Malcolm Brogdon, Robert Williams III, and two first round draft picks.
The Trail Blazers may not be done dealing, but at this point they already have turned an aging, undersized guard who led them to one Western Conference Finals in 11 years into Deandre Ayton, Malcolm Brogdon, Robert Williams III and three first round draft picks plus two pick swaps. The Trail Blazers are not going to win an NBA title any time soon, but it would not be crazy to suggest that their overall roster right now is better than it was before trading Lillard, and it would not at all be surprising if the rebuilding Trail Blazers win at least as many games in the 2023-24 season as they did during the 2022-23 season (33).
Meanwhile, the Celtics not only have one of the NBA's best duos with Jayson Tatum and Jaylen Brown but a good case could be made that the top six players in their rotation are collectively better than any other team's top six players: Tatum and Brown are now flanked by Kristaps Porzingis, Jrue Holiday, Al Horford, and Derrick White. Remember that the Celtics reached the Eastern Conference Finals last year with a six man rotation consisting of Tatum, Brown, Marcus Smart, Horford, White, and Brogdon. Holiday and Porzingis are without question upgrades over Smart and Brogdon.
It is interesting that Holiday demonstrated at least as much market value as Lillard--and more market value than James Harden, who has hardly drawn a sniff of interest around the league. Media members may be very impressed by Harden and Lillard, but when teams have to make critical (and expensive) personnel decisions we see that Lillard and Harden are not viewed as number one options for championship caliber teams: Milwaukee brought in Lillard to be the number two option behind Giannis Antetokounmpo, and Boston gave up at least as much value to get Holiday to be a third or fourth option as Portland received for Lillard.