Michael Jordan had a good relationship with Charles Barkley but hated his poor work ethic, yet Pippen ignored that to team up with him and Hakeem Olajuwon.
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By the end of the 1997-98 season, the Chicago Bulls, after winning Six championships in eight years were breaking up. With it, Michael Jordan was retiring for the second time and Scottie Pippen was looking to sign a huge deal somewhere.
Playing a second fiddle to the arguable GOAT for 9-10 years was one thing and getting massively underpaid was another. And for what he had done in those years, he deserved at least a top-5 salary in the league.
But what he was getting made him the 122nd best player in NBA or worse for years while he was leading the team to championships behind MJ. So, as soon as that dynasty in Chicago dissolved, Scottie decided to team up with Charles Barkley and Hakeem Olajuwon at Houston.
The Houston Rockets had Hakeem Olajuwon, Charles Barkley AND Scottie Pippen in 1998-99, and yet they still lost in the first round of the playoffs. pic.twitter.com/dAxad09y7O
— Basketball Forever (@Bballforeverfb) May 22, 2020
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Michael Jordan warned Scottie Pippen against teaming up with Charles Barkley
Barkley had joined 2x NBA champ Olajuwon to chase rings in ’96. Pippen tried his luck as well teaming up with the former MVPs and also because he was getting a much deserved and way too late — five-year, $67.5 million contract.
Jordan though in some way had advised Pippen to never be teammates with Barkley a year ago. But he didn’t pick it up. He realised it as soon as he teamed up with Chuck and it ended up being a bad environment instead of being a Big-3 team of contenders.
“I probably should’ve listened to Michael (Jordan) a year ago when he said that Charles will never win a championship because he doesn’t show any dedication,” Pippen admitted years after it was all said and done, on ESPN, after Barkley expressed disappointment at Pippen’s desire to leave Houston after just one season.
Scottie had to leave, that Big-3 of declining superstars was never going to work. And Chuck declined the most among the three going from a 23.2 PPG average in his last year (’95-96) in Phoenix to an 8-point decline in just two years.
Eventually, the Rockets were able to trade Pippen to the Blazers before the start of the 1999-2000 season. The Portland team instantly made an impact by almost defeating the eventual Champions LA Lakers in the Western Conference Finals.
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Barkley finally stopped chasing a ring and retired in 2000 as his suffering from injuries and failure to keep up his fitness was getting better of him and he wasn’t anywhere close to the player he used to be.
The Chuckster picked a microphone that very year and became one of the most entertaining analysts of the game in no time. Meanwhile, Pippen has turned out to be a bitter old man who seems to dislike everyone, including Jordan.
