“I’d like them see Scottie Pippen around and give him the just due” – Michael Jordan wanted the Bulls to keep Pippen after the second three-peat originally appeared on Basketball Network.
The sixth title was barely in the rearview mirror when the unraveling began for the Chicago Bulls.
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They had just completed their second three-peat, punctuated by a now-mythic Finals performance from Michael Jordan — a game-winning jumper over Bryon Russell that came to define the closing arc of his prime.
But even as the world stood still for that final shot, the seams holding the dynasty together were already fraying. Behind the scenes, egos clashed, relationships soured and front-office decisions were hugely controversial, to say the least.
Keeping Pippen
Jordan and Phil Jackson were confirmed to be exiting the franchise. Scottie Pippen, arguably the best No. 2 the league had ever seen, was entering free agency after years of contractual dissatisfaction. He’d been severely underpaid throughout the dynasty run, locked into a long-term deal signed in 1991 that no longer reflected his value.
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By 1998, the tension had become public. Jordan offered what many would later read as a parting lament.
“I don’t know what decisions they are gonna make in terms of free agency,” Jordan said. “I’d like them to see Scottie Pippen around and give him the just due that he is very deserving [of]. But that’s just my opinion.”
Jordan had famously declared in 1997 that he wouldn’t play for any coach but Jackson. Jerry Krause had long grown tired of the perceived hierarchy, one that seemed to place players above management. But while the focus often fell on Jackson and Jordan, the quieter tragedy of that summer was the disbanding of one of the most formidable duos in NBA history: Jordan and Pippen.
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Jordan was famously stoic when it came to front-office affairs and this came from a place of concern. He had battled alongside Pippen for over a decade. Their partnership had been crafted in the trenches of Eastern Conference wars against the Bad Boy Detroit Pistons, shaped by Olympic gold in Barcelona and defined by six Finals appearances with zero losses. For all of Jordan’s alpha fire, Pippen had been his perfect counterbalance, unselfish, cerebral and relentless.
Firmly fitted as the team’s Robin, he averaged 19.1 points, 5.2 assists and 5.9 rebounds per game over the 1997–98 season. He played through back spasms in the Finals, pushing his body beyond its limit for the sake of one last ring. If there was any question about his commitment, he’d answered it with sweat and sacrifice. And yet, the Bulls front office looked elsewhere.
In January 1999, just months after hoisting the Larry O’Brien Trophy, Pippen was traded to the Houston Rockets in a sign-and-trade deal.
Dynasty collapse
The Bulls’ breakup wasn’t just about cap space or aging stars. It was about control, pride and a refusal to evolve the hierarchy that had fueled six titles.
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Jordan retired for the second time shortly after the 1998 season.
Jackson left.
Dennis Rodman was gone.
The Bulls couldn’t keep Pippen locked in on a good deal.
What followed was a steep plunge, one Jordan hoped never would happen when he retired.
“We set high standards here and the pressure is on them to maintain that,” Jordan said. “How long will that last? Will it be next year?
“That’s hard for me to say.”
Jordan already seemed to sense what was coming. The 1998–99 Bulls finished the lockout-shortened season with a 13–37 record, dead last in the Eastern Conference. It was a brutal fall from grace and one that underscored the fragility of greatness when mismanaged.
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The five-time Most Valuable Player would return to the NBA in 2001 with the Washington Wizards, but the spark was different. Pippen bounced from the Houston Rockets to the Portland Trail Blazers and back to Chicago in a symbolic final season, but the magic of their prime was gone. The Bulls, once the model franchise, took nearly a decade to regain relevance.
The front office’s failure to honor Pippen’s contributions, both financially and professionally, lingers as one of the NBA’s great “what-ifs.” If Chicago had found a way to keep him happy, a seventh title could have followed.
And maybe the dynasty would have stretched into the early 2000s.
This story was originally reported by Basketball Network on Jun 29, 2025, where it first appeared.