Zach Randolph
While he was more athletic and physically gifted as a young player with the Trail Blazers, Zach Randolph didn't live up to his potential as a two-way power forward with a multi-faceted offensive game until he grew up and matured. He eventually became part of the Memphis Grizzlies' grit-n-grind teams in the 2010s that were regularly competing in the postseason.
Randolph's tenure in Portland was filled with off-court issues that stunted his growth. Being a young, impressionable piece of the Jail Blazers' squad probably didn't help.
The 6-foot-9, 250-pound big man played only one season at Michigan State before entering the 2001 draft, where Portland selected him with the 19th overall pick. He broke out in the 2003-04 season when he averaged a double-double and won the league's Most Improved Player Award at age 22. That led to a massive six-year, $84 million extension with the Blazers.
But consistent off-court issues eventually pushed the franchise to the breaking point. He was cited for underage drinking in 2002, arrested for a DUI in 2003, argued with teammates and was suspended two games and fined $100,000 for punching Ruben Patterson.
In the summer of 2007, Z-Bo was traded to the New York Knicks for Steve Francis and Channing Frye.