Before Steve Ballmer arrived in the NBA and became the wealthiest team owner in pro sports, the Portland Trail Blazers were owned by another Microsoft billionaire, co-founder Paul Allen.
Allen was the majority owner of the Blazers from 1988 until he died in 2018 and Like Ballmer, he was not afraid to spend for his team.
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With the help of Allen’s wallet, the Blazers were able to go on spending sprees that made them one of the top teams in the league during the early 2000s. Former Blazers point guard Damon Stoudamire talked about that short window during his recent appearance on “The Jim Jackson Show.”
“That was the first time where an organization was really paying guys, so guys were all right with taking less minutes because they was giving out that money. Guys was all right with less minutes because we were not necessarily playing for contracts. And at that time, to get those young guys to do that, cuz that whole team was essentially brought in the prime of their careers. Everybody, not one person, everybody,”said Stoudamire.
The Blazers were on the verge of the Western Conference finals in 2000
After getting swept by the San Antonio Spurs in the 1999 Western Conference finals, Blazers GM Bob Whitsitt traded for Scottie Pippen and Steve Smith, while signing veteran Detlef Schrempf. With their new acquisitions, the Portland payroll ballooned to a league-high $73.9 million, including $53.5 million to their starters.
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The investment paid off as Portland won 59 games during the 1999-2000 NBA season and was the number three seed in the Western Conference. The Blazers dropped just one game in each of the first two rounds of the 2000 NBA Playoffs before going neck-to-neck with the Los Angeles Lakers in the 2000 WCF.
Despite taking the Lakers to the full seven-game limit, the Blazers could not complete the job.
“When we lost to the Lakers in Game 7, man, we trade Jermaine O’Neal and Brian Grant. I was like ‘Damn.’ I was like, ‘That’s a tough one, man.’ Jermaine was gonna be Jermaine. Jermaine was coming. And although BG was injured that year, he was still a big part of what we was trying to do and he was an anchor for us because he brought toughness. He was going to lay that wood,” Damon explained.
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Stoudamire said the Blazers got impatient
With O’Neal and Grant gone, the Blazers added Shawn Kemp and Dale Davis via trades while re-signing point guard Rod Strickland. But while Dale was coming off an All-Star year and Shawn was still a 17 points and eight rebounds guy, Stoudamire said that they had to “reinvent the wheel” with two new key pieces.
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Meanwhile, the Blazers had the league’s highest payroll for the second straight year at $87.3 million.
Portland went 50-32 that year and was eliminated in the first round of the playoffs by, well, the Lakers. During the summer, the Blazers added Derek Anderson, Steve Kerr and Ruben Patterson. Portland finished 49-33 for the third straight year, they were eliminated by the Lakers, this time, also via a 3-0 sweep.
“I just think about that window. That Portland window was crazy. And then you know, I think we got impatient. We go to the Conference Finals. My second year with the team, they changed the team and we go to the Conference Finals. My third year, we change the team again,” Stoudamire added.
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During the 2002-03 season, Portland had the league’s biggest payroll once again and at $105.5 million, they were the only team in the league with a payroll to exceed $100 million. Once again, they came up short, this time against the Dallas Mavericks. The Blazers’ streak of 21 consecutive playoff runs ended when they went 41-41 in 2003-04 and missed the playoffs.
That setback ended the short window Stoudamire talked about.
This story was originally reported by Basketball Network on Oct 19, 2025, where it first appeared in the Old School section. Add Basketball Network as a Preferred Source by clicking here.