Coming in at #10 on our All-Time Team full of Most Disappointing Portland Trail Blazers acquisitions is a player who not only fell short in his individual performance but stood as a symbol for the end of an era.
Even though he had bounced to three teams in his four year career when the Blazers acquired him in the summer of 2001, Derek Anderson was still considered a potential diamond in the rough. And yes, we modified the idiom there, making the translation of that phrase "potentially a guy who might have potential". Anderson wasn't a star, but he could have been heading there. Injuries had kept him grounded in his early years with the Clippers, but given more responsibility with the Cavaliers and Spurs respectively the 6'5" shooting guard had averaged 16 ppg over the past two seasons. In San Antonio he developed a three-point shot (40%). He had a little bit of an all-around game, averaging around four rebounds and assists respectively. The Spurs' defense even made that aspect of his game look good. Most importantly for the Blazers, he was only a week past his 27th birthday when they acquired him in exchange for Steve Smith, who was more like a decade past that point.
The tenure of famous Portland Trail Blazers General Manager Bob Whitsitt had three distinct phases. When he joined the team in the early 90's he dismantled the old Drexler-led lineup, converting aging-yet-successful players into younger talent gambles. Isaiah Rider and Rasheed Wallace were prime examples of this era. Enough of those gambles paid off that by the late 90's Whitsitt was able to switch to a diet of experienced veterans to fill in lineup cracks; Scottie Pippen and Smith being exemplary. When the Wallace-Pippen-Smith teams couldn't overcome the Lakers in 2000 Whitsitt began to switch back to his original mode, trading away veterans for the next wave of hidden stars. Anderson and forward Ruben Patterson were the shining paragons of that group.
The difference between the '90's and '00's cycles of young-player acquisition were pronounced, however. For the most part Whitsitt waived the Drexler Era players, using their considerable salary slots to make room for signings, using draft picks and ancillary players to complete trades for new talent. By the early 2000's the Blazers draft picks were low and their ancillary players were worthless either by virtue of ability or because they were ancient and on hugely expensive contracts. Therefore Whitsitt had to convert age into youth via direct trade, as in the Smith-for-Anderson deal. This not only limited his trading partners, it dampened the quality of player he could expect in return. Therefore instead of hosting a true rebuilding project as the 90's had, those years became a desperate grab at B-level players trying to keep a sinking ship afloat.
Enter Derek Anderson.
D.A. was greeted with warm applause by a Portland crowd ready to believe that a return to success was just one young, motivated player away. That applause quickly turned to shrugs as Anderson's play took on the quality of linoleum bathroom floor tile. It's there. It's functional. There's nothing particularly enticing about it. Anderson's scoring average dipped 5 points in real terms and began a per-minute descent that would continue throughout his Portland career. Defense disappeared, the three-point shot deserted him after a year, shooting percentages were soon to fall in the toilet. Oh, did I mention that the Blazers rewarded him with a six-year contract that would end up paying him over $48 million of the $58 million he would eventually earn in his career?
When Anderson began missing games because of toothaches later in his Portland tenure fans turned on him with a vengeance. It wasn't just him. The rest of the team had gone to JailBlazer hell. Anderson was actually one of the last remaining hopes of a player to root for. When his play and his weeks-long boo-boos took him out of contention for applause Portland fans had lost their last hope. Their response mixed frustration with a healthy dose of "et tu, D.A.?" Anderson's fall also stripped Blazer fans of their last illusion that the Whitsitt plan was going to work. The desperate grab at a return to the brief, blazing glory of 2000 had ended in failure so utter as to be irredeemable.
Out of the case and on the finger the potential diamond in the rough was revealed as cubic zirconia. Even though the original expectations for him weren't as high as some of the players who made this list, the symbolic nature of his quite tangible letdown was enough to earn Derek Anderson the #10 spot on our list.
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