“I asked Phil, ‘Are you getting back into the game?'” – Scottie Pippen said he tried to team up with Shaq and Kobe after failed Houston stint originally appeared on Basketball Network.
At the twilight of his storied run with the Chicago Bulls, Scottie Pippen found himself on unfamiliar ground.
Advertisement
The dynasty that had once dominated the NBA was crumbling from the inside out. Michael Jordan had retired (again), Phil Jackson was no longer at the helm and the front office had made it clear that a rebuild was on the horizon.
After 11 seasons, six championships and establishing himself as the franchise’s second all-time leader in points, assists and steals, Pippen was shipped off to the Houston Rockets in January 1999 in a sign-and-trade deal.
Chance to play in L.A.
By the end of that lockout-shortened season, it was clear that Houston wasn’t the long-term answer. The team fell in the first round of the playoffs to the Los Angeles Lakers and with the summer approaching, Pippen was already looking for the next door out and right at the same time, his former head coach was lined up to coach the Lakers.
Advertisement
“I asked Phil, ‘Are you getting back into the game?’ And he said, ‘Yeah.’ And I said, ‘Alright,” Pippen recalled. “So I called my agent and I was like, ‘Can you try to get me traded to the Lakers?”
Houston was supposed to be a fresh chapter alongside Charles Barkley and Hakeem Olajuwon — on paper, a Hall of Fame trio poised to contend. Pippen’s lone campaign with the Rockets was tense and underwhelming, his fit in Rudy Tomjanovich’s system never clicked and his relationship with Barkley quickly soured.
Jackson, who had taken a year away from coaching after being ousted by Bulls management, was preparing for his return — but this time in Los Angeles.
The Lakers had just been swept by the San Antonio Spurs, but the core was there. A 26-year-old Shaquille O’Neal was entering his prime and Kobe Bryant, just 20 years old, was beginning to morph from teenage sensation into something more dangerous.
Advertisement
For Pippen, the thought of reuniting with Jackson and molding a championship core with O’Neal and Bryant wasn’t some dream cooked up in hindsight. It was a real pursuit. A calculated pivot by a veteran looking to win, again.
The lost trio
At the time, the Lakers were still sorting out their identity. The front office had made major moves in recent years, but cohesion remained elusive.
Adding someone like Pippen, a defensive savant, seasoned winner and vocal leader, could have added stability. But the logistics proved harder than the idea itself.
Advertisement
“They started talks with Houston, I kind of let Houston know I wasn’t happy,” Pippen admitted. “But the moral of the story — I wasn’t able to play with Shaq.”
By late summer 1999, the Lakers had shifted focus elsewhere. Jackson came in, but the Pippen reunion never materialized. With his exit from Houston all but confirmed, the six-time champion was rerouted to the Portland Trail Blazers, a team brimming with talent but short on harmony.
The 1999–2000 Blazers — which included Rasheed Wallace, Damon Stoudamire, Steve Smith and Arvydas Sabonis — were stacked but combustible.
They made it all the way to the Western Conference finals and came within a quarter of knocking off the Lakers in Game 7 before that infamous collapse where Portland squandered a 15-point fourth-quarter lead. The irony lingered as the team Pippen wanted to join, the Lakers, went on to three-peat. The team he chose instead never reached the Finals.
Advertisement
Across his five seasons post-Chicago, Pippen’s numbers dwindled; he averaged just 12.5 points per game with Houston and Portland combined, but his veteran presence remained valuable. Still, that unmaterialized link-up with O’Neal and Bryant was one he wished had happened.
This story was originally reported by Basketball Network on Jul 15, 2025, where it first appeared.