Rip City had a relatively successful run with Damian Lillard, at least in terms of their regular season records. From 2012-23, they were 422-347, a 55 percent win rate. But they only made one Western Conference Finals the entire time Lillard was in Portland.
In general, the Blazers failed to get Lillard more help on the roster. But, there are a few particular players that they had and decided to move on from too soon. Many questioned the Blazers' decision to move on from these players at the time. But it's even worse in retrospect now that all these players have succeeded with their next team.
1. Nic Batum
The Houston Rockets initially selected Nic Batum with the No. 25 pick in the 2008 NBA Draft. The Blazers did an excellent job of acquiring him, trading away the rights to Darrell Arthur (No. 27 pick) and Joey Dorsey (No. 33 pick). Batum had seven productive seasons with the Blazers, averaging 13.1 points, 5.9 rebounds, 3.5 assists, and 1.1 steals per game during that stretch.
But where they went wrong was trading away Batum after the 2014-15 season. He was entering his prime at 26 years old and went on to have the best seasons of his career right after leaving Portland, averaging 15.4 points and 16 points per game in his first two of five seasons spent in Charlotte.
To make matters worse, the Blazers traded Batum away in exchange for Gerald Henderson and Noah Vonleh. Henderson was on an expiring deal, so the trade was centered around gambling on Vonleh. The Blazers were coming off of back-to-back 50-win seasons, yet decided to trade away a proven Batum just entering his prime for a 19-year-old Vonleh who was coming off of a rookie season in which he averaged 3.3 points per game. Vonleh was arguably the worst starter Lillard played with his entire time in Portland.