Michael Jordan made his case in “The Last Dance” for Chicago to make another championship run in 1999. He went through a list of Bulls – himself, Phil Jackson, multiple role players – he says would have signed one-year contracts. Then, he got to Scottie Pippen.
“Now, Pip, you would have had to do some convincing,” Jordan said in the ESPN documentary. “But if Phil was going to be there, if Dennis was going to be there, if MJ was going to be there to win that seventh, Pip is not going to miss out on that.”
Bulls owner Jerry Reinsdorf, via Ramona Shelburne of ESPN:
Reinsdorf is probably right. Pippen got a reported five-year, $67 million contract with the Rockets (via sign-and-trade) in 1999. As his previous deal with the Bulls showed, Pippen valued long-term security. It would’ve been quite risky – given his age (32) and health issues – to reject that Houston contract and hope for another big offer in 2000.
And Jordan overstates Pippen’s commitment to winning championships. Pippen demanded a trade in 1997, right in the midst of a three-peat! Of course, Pippen wanted to win. He also wanted to be on a team that’d pay him what he felt he was worth.
But why did it have to be a one-year contract?
Reinsdorf is deflecting. He could could have re-signed Pippen to a long-term deal. It’s Reinsdorf’s money and his right not to spend it. But it’s ridiculous to frame the discussion as if a one-year contract were Chicago’s only option.
Pippen’s five-year contract aged poorly in Houston then Portland. He was past his prime and not worth his high salary. But value can’t be evaluated in a vacuum. It might have been worth paying out a “bad” five-year contract if it meant another season of championship contention. After six titles in eight years, the Bulls were so spoiled to throw that away.
Jordan and Jackson were clearly exhausted by the end of the 1998 run. Most of Chicago’s supporting players – including Pippen – were aging. Maybe 1999 would’ve been the last run even if the team were kept intact. But even if that were the case, the Bulls probably still could have traded Pippen for at least neutral value in the 1999 offseason. That would have been a great situation – getting an extra season of championship contention while paying Pippen only one extra season.
After having him for only season, the Rockets traded Pippento the Trail Blazers for Kelvin Cato, Walt Williams, Carlos Rogers, Stacey Augmon, Brian Shaw and Ed Gray. So many years later, it’s difficult to evaluate exactly how Houston valued that package. It seems mostly positive, though.
The Rockets showed plenty of faith in Cato, signing him to a six-year, $42 million extension shortly after the trade. ESPN’s season preview included rave reviews of both Cato…:…and Williams:
Small forward
This is where the Rockets really upgraded themselves, even though that may seem a reach since they lost Pippen. In Williams, they got the small forward they’ve been chasing for years. Remember, he was one of the players they coveted in that ill-fated trade they had set up with Toronto two seasons ago that would’ve also landed them Damon Stoudamire. Williams gives the Rockets a legitimate small forward, a guy who can knock down the three -- a must in the team’s halfcourt sets -- post up when needed and create his own shot off the dribble.
Williams (more useful) and Rogers (less useful) were on hefty contracts that lowered their values. Augmon, Shaw and Gray amounted to dead salary for the short term.
Still, if the Bulls could’ve contended for a championship an extra year then turned Pippen into a package like that, that would have been GREAT for Chicago.
The Bulls might have gotten even more. Pippen probably wouldn’t have had a worse season in Chicago (where he had chemistry with Jordan, Jackson and everyone else) than he did in Houston (where he struggled to fit with Hakeem Olajuwon and Charles Barkley and clashed personally with Barkley).
Of course, there would have been risk for the Bulls. Pippen could have declined even more quickly, leaving a large long-term contract extremely toxic. Reinsdorf didn’t want to potentially incur those costs – EVEN THOUGH THE UPSIDE WAS ANOTHER CHAMPIONSHIP.
