Bob Whitsitt - Portland Trail Blazers

Portland Trail Blazers

During the first two years of his tenure, Whitsitt oversaw an aging roster that had been to the Finals earlier in the decade, but needed serious retooling.

In the 1996 off-season, Whitsitt began to make his mark with several moves. He traded for guard Isaiah Rider and forward Rasheed Wallace, and signed guard Kenny Anderson to a free agent contract. He also drafted high-school player Jermaine O'Neal in the draft. These moves made the Blazers a better team in the short run (in 1999 and 2000 the Blazers advanced to the Western Conference finals), but criminal activity of some players Whitsitt acquired began to grate on the Portland fan base; many started to refer to the team as the "Jail Blazers".

Whitsitt's reputation started to turn sour after the 2000 season, when the team executed several controversial moves. Popular player Brian Grant opted out of the final three years of his contract and was traded away in exchange for Shawn Kemp; and center-forward Jermaine O'Neal was traded for Dale Davis. Both players were unhappy with their roles and asked to be traded. These moves were made to push the team "over the hump" (the Blazers went to the Western Conference finals), but they backfired spectacularly—Kemp was a bust, and O'Neal went on to become an All-Star for the Indiana Pacers. In addition, Whitsitt further alienated the Portland fan base by acquiring Seattle forward Ruben Patterson, a convicted sex offender, via free agency.

Even before the disastrous 2000 off-season, many questioned Whitsitt's evaluation of basketball talent. For one thing, Whitsitt never shied away from players with checkered pasts; this often upset fans; it was also alleged that such players—while talented—lacked the emotional maturity necessary to be a "winner". For another thing, Whitsitt was accused of not paying attention to team "chemistry", or how the various players might interact on the floor (or in the locker room). Whitsitt himself was famously quoted as saying that he "never studied chemistry in college". The result of this, it is claimed, are teams that make inefficient use of the talents available; or which are "less than the sum of their parts". Whitsitt has also been criticized for attempting to stock teams with "All-Star" caliber players (including for bench roles), leading to conflicts over playing time and reduced team camaraderie.

Many other players acquired by Whitsitt have had significant off-court or legal issues (either with the Blazers or elsewhere); these include:

• Gary Trent (drafted in 1995)
• Jermaine O'Neal (drafted in 1996)
• Rasheed Wallace (acquired by trade in 1996)
• Isaiah Rider (acquired by trade in 1996)
• Damon Stoudamire (acquired by trade in 1998)
• Bonzi Wells (drafted in 1999)
• Shawn Kemp (acquired by trade in 2000)
• Rod Strickland (signed as free agent in 2001)
• Zach Randolph (drafted in 2001)
• Ruben Patterson (signed as free agent in 2001)
• Qyntel Woods (drafted in 2002)

After the 2003 season, Whitsitt resigned his position with the Trail Blazers and was replaced with Steve Patterson as the team president and John Nash as the general manager.