5. The Trail Blazers gave up too soon on Zach Randolph
Initially, Zach Randolph fit the bill for a player the Trail Blazers didn’t give up on. The 6’9″ power forward was drafted 19th overall out of Michigan State in the 2001 NBA Draft, and he averaged just 2.8 points per game as a rookie and 8.4 per game in his second year. Those Portland teams were strong and Randolph didn’t have much of a role.
He bullied his way into the rotation from there, however, breaking out in his third season and averaging 20.1 points per game. He continued his post-scoring and ferocious rebounding for the next few seasons, earning a lucrative contract from Portland.
Unfortunately for Randolph and the Blazers, a number of off-court incidents eroded their belief in him. As Portland faced the music about becoming a rebuilding team, they decided that the best way to handle Randolph was to essentially dump his contract on the New York Knicks.
Randolph spent 80 games with the Knicks and 39 with the LA Clippers before finding his way to the Memphis Grizzlies, where he would put his character concerns and off-court distractions behind him and contribute to winning basketball. He became a beloved and critical member of the Grit ‘N Grind Grizzlies and was named to two All-Star games.
Perhaps Randolph doesn’t find that level of success in Portland, but if they put the right culture around him he could have blossomed and at the very least been more valuable in a trade than simply dead money. He was a really talented player and the Blazers gave up on him way too soon.