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Blazers Top 100: Golden Boy Goes Boom

A look at the 100 players and personnel who have influenced the Trail Blazers’ 50-year history.

Whitsitt poses

The Trail Blazers’ 50-year anniversary season is temporarily on pause as the NBA goes on hiatus to slow the spread of COVID-19. During that break, Blazer’s Edge is counting down the top 100 Blazers: players, executives, and other influencers who made the franchise what it is today.

No. 38 | Bob Whitsitt

General Manager: 1994-2003

Place in History: Bob Whitsitt’s tenure as Portland Trail Blazers General Manager is inextricably bound with its end. He left the town a bloated, expensive, underachieving roster, having alienated Portland media and most fans in the process. It was a flaming disaster of a conclusion that belied promising beginnings.

In 1994, Whitsitt took over what might as well have been your grandmother’s Trail Blazers. The players weren’t old, nor had they been together for decades. Instead they had gone through the crucible of the 1990 and 1992 NBA Finals without emerging with a trophy. The roster was still intact, but it wasn’t going anywhere. Clyde Drexler was experiencing intermittent injuries and wasn’t the league-defying superstar he had been a couple seasons prior. He played alongside quality players with big local cachet, but none of them were going to lead the team to the promised land. The Blazers were like an upscale Applebee’s. They were decent, but you knew what you were going to get and it was not going to be five-star material.

In July of 1994, owner Paul Allen shook things up by bringing in a hot, young chef. Whitsitt had spent eight years with the Seattle Supersonics, guiding them into playoffs contention by drafting Gary Payton and Shawn Kemp and hiring George Karl as Head Coach. Whitsitt won NBA Executive of the Year in 1994, but was on the outs with owner Barry Ackerley. Seeing greener fields in Portland, he jumped to billionaire Paul Allen’s franchise and began to rebuild.

Whitsitt’s first couple seasons were full of sad goodbyes. Head Coach Rick Adelman had been fired before Whitsitt arrived. Drexler, Jerome Kersey, Kevin Duckworth, and Terry Porter weren’t far behind. (Whitsitt showed little respect for tradition; Kersey was left open in an expansion draft and Porter was simply released.) Cliff Robinson appeared to be the only firm holdover from the Finals years, and even he wouldn’t last forever.

With the cupboards clear, Whitsitt got to work compiling ingredients that few envisioned working together. He drafted high school prospect Jermaine O’Neal, traded for Rasheed Wallace and Isaiah Rider, signed Kenny Anderson and Brian Grant. The once-staid Blazers began to look like a hot, happening destination spot.

As Whitsitt continued to bring in talent, Allen opened his deep, billionaire wallet wider and wider. He had inherited the ultra-successful Drexler-led rosters. This would be his chance to assemble a team of Super Friends through his wunderkind GM. He took full advantage.

Everybody understood that the roster was still in flux. It had taken seven years for the Blazers to win their original title; it took seven more after drafting Drexler to make the Finals. Players coming in and out was hardly surprising during a rebuilding phase. Whitsitt took it to another level. Players would come one year, only to be traded a season and a half later in the next step upwards. Portland’s transaction sheet began to look like a Who’s Who of available talent. Whitsitt turned the mom-and-pop trade store into Costco, buying in bulk and selling just as quickly.

Three moves defined Whitsitt’s early years—and philosophy—more than any others.

In February, 1998, Whitsitt moved three players (Anderson, Gary Trent, and Alvin Williams) plus three draft picks to the Toronto Raptors for former Rookie of the Year point guard Damon Stoudamire. A home-town product and 20-point scorer, Stoudamire was slated to be the crown jewel of Portland’s future plans, the backcourt complement to Wallace in a formidable one-two punch.

But one-two wasn’t good enough for “Trader Bob”. He wanted to throw punches 18-32 and land them just as heavily. In the Summer of 1999, following a trip to the Western Conference Finals, Whitsitt traded Rider and Jim Jackson (both acquired during his tenure) to the Atlanta Hawks for veteran All-Star Steve Smith.

That would have been a sufficiently big coup for most teams, but it wasn’t even the biggest move of the summer. Two months later, Whitsitt would send Stacey Augmon, Kelvin Cato, Ed Gray, Carlos Rogers, Brian Shaw, and Walt Williams to the Houston Rockets for Scottie Pippen. Yes, THAT Scottie Pippen. The move sent seismic ripples through the NBA, absolutely upending expectations in Portland while cementing Whitsitt’s genius.

A coda: The only player that the Blazers might have regretted losing in the Pippen deal (until Shaw hit an unfortunate shot for the Lakers in that season’s playoffs) was Augmon. The Rockets waived him and the Blazers got him right back anyway. That was the way Bob Whitsitt trades worked.

Let’s recap. In four years (1995-1999) the Blazers had gone from liquidating an iconic but aging roster to assembling a rotation of Rasheed Wallace, Scottie Pippen, Damon Stoudamire, Steve Smith, Arvydas Sabonis, Brian Grant, Jermaine O’Neal, Greg Anthony, Bonzi Wells, Detlef Schrempf, and Stacey Augmon.


Neither the Blazers nor the NBA had seen anything like it. Give that chef a Michelin Star.

A memorable, heartbreaking Game 7 loss to the Los Angeles Lakers in the 2000 Western Conference Finals proved the pivot point for Whitsitt’s legacy. He had pulled the slot machine handle and hit the jackpot, but like a compulsive gambler, he didn’t cash out. He’d end up putting all of his winnings back in the machine and more, losing in spectacular fashion.

The downturn started when the Blazers traded Grant in a three-team deal that netted them former Sonics forward Shawn Kemp. By this time, Kemp was several pounds heavier, much less explosive, and about a billion times more expensive than he had been when Whistitt drafted him in Seattle. Grant’s impending free agency and discontent in a crowded frontcourt forced the deal—the rare occasion when Whitsitt didn’t control his own destiny—but it took less than three months to figure out Kemp was the wrong target.

The day after that, Whitsitt moved young phenom O’Neal to the Indiana Pacers for All-Star forward-center Dale Davis. Davis was a great defender and rebounder, but was aging out of his prime and was not going to be a long-term answer.

Portland’s revamped roster won 50 games in the regular season, but couldn’t take even one in an anticlimactic rematch against the Lakers in the first round of the 2001 NBA Playoffs.

The Blazers drafted Michigan State forward Zach Randolph with the 19th pick of the 2001 NBA Draft. It was a steal, but Randolph brought his own issues with him which would blossom as his career progressed. Stories like this would become commonplace during the next few years.

On paper, Whitsitt’s new-millennium moves looked similar to those of the 1990’s. In practice, the returns on them became less and less, and came with more asterisks attached. The Blazers traded Smith for Derek Anderson. They signed troubled forward Ruben Patterson to a free agent deal. They drafted Qyntel Woods. None of these deals worked out.

By 2002, the Blazers were paying an exorbitant amount to keep players who were laying eggs on the court and earning unwanted attention off it. The former Golden Boy GM was embattled in feuds with local media members, flailing in his fortress kitchen, still trying to find the combination that would make it right.

In the end, it never came. Whitsitt exited after the 2002-03 season, leaving behind an unholy mess for President Steve Patterson and General Manager John Nash to clean up. It would take three years before the Superfund site was cleared and the franchise found an upward trend again.

Bob Whitsitt will be remembered for the Jail Blazers disaster, his supreme self-confidence in dealing with the media and public, and his overactive trade ledger. He should also be remembered for creating one of the best rosters in franchise history, falling behind only the 1977 Championship team and the Drexler Finals teams for success.

Love him, hate him, or both, Whitsitt had a huge impact on the Trail Blazers. He absolutely earns the 38th spot on our list of Top 100 Trail Blazers players and influencers, and probably should go much higher.

Share your memories of “Trader Bob” below, and stick with us as we continue towards #1!

Lakers v Trail Blazers fan