Scottie Pippen is widely regarded as one of the greatest small forwards in NBA history, with a career that spanned 17 seasons and included six NBA championships with the Chicago Bulls.
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However, his time with the Portland Trail Blazers, from 1999 to 2003, is often overlooked and overshadowed by his success in Chicago. Pippen was traded to the Trail Blazers in the summer of 1999, at the age of 33.
He was expected to be the missing piece that would help the Blazers compete for a championship. They had fallen short in the playoffs in previous years. Along with Pippen, the Blazers also added veteran center Arvydas Sabonis and point guard Steve Smith to their roster.
The Blazers finished the regular season with a 59-23 record, the second-best in the Western Conference. But they were ultimately eliminated in the Western Conference Finals by the Los Angeles Lakers.
Scottie Pippen turned down the chance to play alongside Kobe Bryant and Shaquille O’Neal
The Lakers were among the teams interested in finalizing a deal for the 6-time NBA champion and All-Star. However, Portland beat them to the punch by sending 6 players and a draft pick to Houston.
Scottie Pippen clarified that he preferred to be in Portland compared to playing alongside Kobe and Shaq in LA:
“This is far more talented than any team that has been assembled in the league … as far back as I can remember. We’re far more talented than the Lakers and far ahead of where the Lakers are trying to get to.”
“I would probably have chosen this team [over the Lakers] because I feel it is more on the verge of winning a championship. There had been a great chance to win even without Scottie Pippen.”
Pippen’s assertion wasn’t an unreasonable one. The Blazers, after all, were coming off a Conference Finals loss to the Spurs in 1999. However, he missed a chance to play reunite with his former coach, Phil Jackson, alongside 2 top-10 players ever.
How did Pippen’s tenure in Portland turn out?
In his first season with the Blazers, Pippen struggled with injuries and missed 24 games. However, he still managed to average 12.5 points, 6.3 rebounds, and 5.0 assists per game. He also earned his eighth All-Defensive Team selection.
While Pippen’s time in Portland was not as successful as his time in Chicago, he still made a significant impact on the Blazers’ success during his tenure.
His veteran leadership, defensive prowess, and versatility were invaluable to the team, and he played a key role in helping them reach the Western Conference Finals. Nevertheless, he could’ve won as many as 3 more rings had fate sent him on a different path.
