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Should the Bulls have traded Scottie Pippen to the Celtics?

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The Jordan Rules author thinks the Bulls could’ve won it in 1997 with a sought-after Tracy McGrady. How would the move have fared for Boston?

Rick Pitino reached out to the Bulls in the summer of 1997 about the Bulls’ five-time champion star forward Scottie Pippen. The Celtics had devastatingly landed the No. 3 pick in a draft where they needed No. 1 for Tim Duncan. Disinterested in the pick, Pitino coveted a veteran instead. Jerry Reinsdorf, the Bulls’ owner, called the trade off before the sides could agree.

That began a tumultuous era for both teams. Pippen, angry over his contract, opted for surgery late and missed the early portion of the 1998 season. Chicago traded him to the Rockets on his last legs after the Bulls’ three-peat. They haven’t won since. It took the Celtics 20 years to build their next title team.

Sam Smith, the author of Jordan Rules who covered that era, believes the Bulls should’ve pulled the trigger. He joined Bob Ryan and Jeff Goodman’s podcast to provide more context around Phil Jackson, Jerry Krause and Pippen.

Regardless of what a broken Pippen would’ve meant for Boston, the No. 3 and/or No. 6 overall in the ’97 draft would’ve given the Bulls a chance to draft Tracy McGrady. McGrady would’ve been Michael Jordan’s worthy No. 2 immediately and the centerpiece of Chicago’s future, always having been a highly sought commodity by Krause. Ron Harper’s 1999 Bulls went 13-37 with McGrady falling to Toronto instead, beginning a seven-year playoff drought for Chicago.

“They’d probably win (in ’98),” Smith said. “Then they wouldn’t have to go to the bottom like they did.”

Smith said the Bulls knew of Jordan and Phil Jackson’s intention to step away in 1998 regardless of what moves Chicago made. That made it apparent that Krause’s rebuilding dream needed to begin, but Jerry Reinsdorf wanted the core to make one last run — which they did. Sound familiar, New England?

The Jordan Rules author also discussed how Phil Jackson became such a trusted source for him and why. He believes Jackson’s strategy to keep Michael Jordan within the team dynamic was to create outside enemies. The Jordan dynamic proved complicated for Pippen and role players alike.

Pippen moved between Horace Grant, uninterested in Jordan’s allure, and the atmosphere of Jordan in the locker room. MJ pressed him to improve, but the subsidiary effect of being around Jordan frustrated as he attempted to craft his own identity.

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