Scottie Pippen entered limbo after Michael Jordan retired in 1998. The Chicago Bulls had no choice but to disband their team and start anew. Pippen joined the Houston Rockets with fellow legend Charles Barkley — a partnership that resulted in a playoff appearance but did not convince Pippen to stay.
Making a decision where to continue his career
As such, ahead of the 1999-00 NBA season, Pippen was traded to the Portland Trail Blazers. In the 2018 book "Jail Blazers: How the Portland Trail Blazers Became the Bad Boys of Basketball" by Kerry Eggers, the introductory press conference of Pippen suggests the forward had control of where he wanted to go.
“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 said then.
He added: “It would be great to win for this group of coaches and players and staff, and for the fans. I think this city deserves it. I’m looking forward to the challenge.”
For some context, the Lakers were already on the verge of blowing up that season. After acquiring Shaquille O'Neal in 1996, he immediately formed a deadly duo with the young Kobe Bryant. Early in their partnership, they guided the Lakers to multiple playoff appearances — even as far as the Western Conference Finals against the Utah Jazz in the 1998 NBA Playoffs. The young Lakers were so good that it attracted Phil Jackson — who had taken a year off after Michael Jordan retired — to take the coaching helm.
Pippen admits joining the Blazers was a mistake
It is rather interesting amid the Lakers' searing potential and the presence of the Zen Master that Pippen chose the Trail Blazers. Like the Lakers, the Portland squad had many young guns like Isaiah Rider and Rasheed Wallace. They had also been active in building a contending squad and had acquired the likes of Damon Stoudamire and Brian Grant. Veterans like Kelvin Cato, Arvydas Sabonis, and Stacey Augmon were also there to provide veteran leadership.
The Trail Blazers had been a perennial playoff team even after the departure of Clyde Drexler early in 1995. This was proof that the organization remained firm in the quest for the title. But unlike the Lakers, they were easily booted out in the first round of the playoffs. It was only until the 1998-99 NBA season that the Trail Blazers showed latent potential by making it to the Western Conference Finals. So the question still remains: why did Pippen choose the decent but unproven Blazers team over the mighty Lakers?
While Pippen seemed to have complete control over where he wanted to go, the decision ultimately relied on the team. A report from October 1999 revealed that then-owner Jerry Buss was hesitant in absorbing the defensive stalwart. From his point of view, Pippen's massive $67 million contract would hurt the organization's plan of acquiring more significant assets.
"Phil definitely felt that Scottie would be a big improvement for us in the next year or two," Buss told a gathering of reporters Wednesday at training camp."
"But he is aware that if you take somebody like Scottie with a long-term contract under the current rules, it would have been impossible to ever improve this team," Buss said, the Associated Press.
Without the benefit of hindsight, one could say that Pippen definitely made the right move. In his first season with the Blazers, they made it back to the Western Conference Finals and were booted out by the Lakers in seven games. Pippen was correct in his assumption that either the Lakers or the Blazers will win it all.
But after that season, the Trail Blazers failed to keep up. They made the playoffs every year but couldn't get past the first round. Some two decades after deciding to go to Portland, Pippen now tags it as one of the greatest regrets of his career. According to him, he should have chosen a veteran squad. This would have enabled him to rest in the regular season and then go full-throttle in the playoffs.
To be fair with Pippen, he had to navigate a tricky path after the end of the Bulls dynasty. One could even say that he had a chip on his shoulder. He wanted to prove he could win without Michael, and even though he was close that year with the Blazers, winning a championship without Jordan never came to completion.