When people talk about Scottie Pippen, they usually picture the red and black of the Chicago Bulls. They see the six rings. They see the frantic defense alongside Michael Jordan. But there’s this whole other era that gets shoved into a footnote, and honestly, it’s arguably the most fascinating part of his career.
I'm talking about the Scottie Pippen Portland Trail Blazers years.
It wasn't just a "twilight of his career" stopover. It was a four-year window where Pippen almost did the impossible: winning a championship as the primary veteran leader of a team that wasn't the Bulls. He wasn't the "best" player on the floor anymore—that was Rasheed Wallace—but he was the heartbeat of a squad that came within a few minutes of changing NBA history forever.
The 1999 Trade: Escaping the Houston Disaster
Before Scottie landed in Portland, he had a miserable cup of coffee with the Houston Rockets. It was supposed to be a "Superteam" with Hakeem Olajuwon and Charles Barkley. Instead, it was a mess. Pippen and Barkley clashed immediately. Scottie famously called Barkley "selfish" and "fat." He wanted out.
Then came the trade. October 2, 1999.
Portland sent a massive haul to Houston just to get the 34-year-old Pippen. We’re talking six players: Stacey Augmon, Kelvin Cato, Walt Williams, Brian Shaw, Ed Gray, and Carlos Rogers.
Why did Portland do it? Because the Blazers were "The Deepest Team in Basketball," and they needed a grown-up in the room. They had Rasheed Wallace, Steve Smith, Damon Stoudamire, and Arvydas Sabonis. They had talent coming out of their ears, but they lacked that championship DNA.
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Pippen walked into the locker room and basically told everyone, "This is the most talented team I've ever seen." He wasn't just blowing smoke. The 1999-2000 Blazers were a wagon.
The 2000 Western Conference Finals: What Really Happened
If you want to understand the Scottie Pippen Portland Trail Blazers era, you have to look at the 2000 Western Conference Finals against the Lakers.
This was the peak.
Portland won 59 games that year. They cruised through the first two rounds. Then they ran into Shaq and Kobe. Most people remember the "Alley-Oop" in Game 7, but they forget that Portland was up by 15 points in the fourth quarter.
Fifteen points.
Pippen was the guy holding it together. In the series-clinching win against the Jazz in the previous round, he had 23 points, 9 rebounds, and 8 assists. He hit the go-ahead three-pointer with 7.3 seconds left. He was still "Point Scottie."
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But in that Game 7 against the Lakers, everything broke. The Blazers missed 13 straight shots. The officiating—to this day, a sore spot for Rip City fans—felt lopsided. The Lakers shot 37 free throws to Portland’s 16.
Pippen played 45 minutes in that Game 7. He finished with 12 points, 10 rebounds, and 3 assists. He did the dirty work, but the offense stalled. If Portland wins that game, they almost certainly beat the Indiana Pacers in the Finals. Scottie would have had seven rings, and the "he only won because of MJ" narrative would have died right there.
More Than a Stat Sheet
Look, Pippen’s numbers in Portland won't jump off the page at you.
- 1999-00: 12.5 PPG, 6.3 RPG, 5.0 APG
- 2000-01: 11.3 PPG, 5.2 RPG, 4.6 APG
- 2001-02: 10.6 PPG, 5.2 RPG, 5.9 APG
- 2002-03: 10.8 PPG, 4.4 RPG, 4.5 APG
He wasn't the 20-point scorer he was in Chicago. His back was hurting. He’d had surgeries. He was older.
But his impact was about leadership and IQ. Take Rasheed Wallace, for example. Sheed was a walking technical foul. Pippen used to go out of his way to argue with refs before Sheed could, just so Pippen would take the technical instead of his star power forward. He literally sacrificed his own stats and reputation to keep his younger teammates on the floor.
He was the "Point Forward" before that was a trendy term for everyone. On a team with a scoring point guard like Damon Stoudamire, Scottie was often the one actually initiating the sets.
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The "Jail Blazers" Transition
Unfortunately, the Scottie Pippen Portland Trail Blazers era coincided with the start of the "Jail Blazers" reputation. After that 2000 collapse, the front office panicked. They traded away Jermaine O'Neal—who Scottie later said was clearly the future of the franchise—for Dale Davis.
Pippen hated it. He felt they "busted the team up" way too early.
The chemistry soured. Pippen stayed professional, but the team started losing in the first round every year. By 2003, his body was mostly done. He headed back to Chicago for one final season, but the Portland years were his last real stand as an elite NBA force.
Actionable Insights for Fans and Historians
If you’re revisiting this era, don’t just look at the box scores. You have to watch the tape to see how he manipulated the defense. Here is how you should actually value Scottie's time in Rip City:
- Watch the 2000 Game 5 vs. Jazz: This is Pippen at his absolute veteran best. He controlled every single aspect of that game without needing to take 25 shots.
- Analyze the Defensive Rotations: Even at 35, Scottie was still an All-Defensive Second Team selection (2000). He was the one calling out rotations for Sabonis and Wallace.
- Re-evaluate the Trade: Most "win-now" trades fail. This one actually worked—it put Portland in a position to win a title. They just didn't close the door.
- The Jermaine O'Neal Factor: Listen to Pippen’s later interviews about Jermaine O'Neal. It provides a massive "what if" regarding Portland's management during that time.
The Scottie Pippen Portland Trail Blazers years weren't a failure. They were a masterclass in how a superstar transitions into a role player while maintaining the soul of a champion. It’s a shame a 15-point lead evaporated in Los Angeles, because Portland deserved that trophy, and Pippen deserved that seventh ring.
To see the real impact, you can look into the full season archives on Basketball-Reference or check out the "Throwback NBA" highlights of the 2000 WCF. Seeing Scottie navigate that Lakers defense is still a treat for anyone who loves high-IQ basketball.