"I'm grateful I was able to move on before the ship started sinking" - Pippen had no regrets leaving the Bulls after MJ's second retirement

“I’m grateful I was able to move on before the ship started sinking” – Pippen had no regrets leaving the Bulls after MJ’s second retirement originally appeared on Basketball Network.

The Chicago Bulls pressed the reset button hard after Michael Jordan‘s retirement in 1998. Head coach Phil Jackson took some time off coaching, while Scottie Pippen found himself donning the Houston Rockets jersey. It was a championship chase that fell flat on its face. Despite joining forces with legends Charles Barkley and Hakeem Olajuwon, the star-studded Rockets got eliminated in the first round of the playoffs.

No regrets

The following year, Pippen embarked on a new journey with the young Portland Trail Blazers. Some fans were dismayed at how the star small forward seemed to struggle to find a new home after his glory years in Chicago. Amid such concerns, Pip assured that he was at peace with leaving the Bulls. He didn’t want to be part of a rebuilding team.

“I have no bitterness. I’m grateful I was able to move on before the ship started sinking,” Pip said via the Chicago Tribune.

“Without the opportunity to be competitive after who I played with, I wouldn’t want to take that beating,” Pippen said.”Every team in the league is enjoying the opportunity to come into Chicago and beat them now. I didn’t want to be on that side, taking the beatings. They’re really suffering right now, but they got what they asked for.”

A long and winding road

The 1998-99 Bulls roster was almost unrecognizable. Only Ron Harper, Toni Kukoc, Randy Brown, and Bill Wennington remained from the previous year. The rest were unknown veterans, inexperienced rookies, and second-year players. At face value, the Bulls could craft a team around five-year man Kukoc. However, Bulls general manager Jerry Krause seemed uncertain about their next move.

“I don’t think anyone would ask me,” Pip continued. “If it’s an opportunity for a player, he’ll do whatever he wants. But you’re talking about a guy going there and having to make a significant difference to the team. I don’t think [big-name free agents] want that challenge. The nucleus of the team is not good enough to draw free agents. And they don’t know what they’ll be doing with Toni [Kukoc] now.”

Pippen felt it would take years for the Bulls to get back on their feet. The succeeding drafts would be paramount. Scouts have to keep tabs on talent, both hidden and obvious.

“I hate to see them struggle like that,” Scottie said. “I’m sure it’s hard to go to work every day. You don’t have anything positive to look forward to. They almost have to play perfect basketball to win a game.”

In the lockout-shortened 1998-99 season, the Bulls clawed to a 13-37 record. They drafted Duke standout Elton Brand as their first pick after the season, but surprisingly traded him to the Los Angeles Clippers after just two years. Solid players like Ron Artest, Jay Williams, Tyson Chandler, Ben Gordon, and others would don the Bulls jersey, but they all failed to replicate Jordan’s success.

It would take six years after Jordan’s departure for the Bulls to return to the playoffs. The farthest they went was the 2011 Eastern Conference Finals, led by Derrick Rose and coach Tim Thibodeau. Rose’s injuries killed the team’s momentum, and up until now, the Bulls have been a bottom-feeding squad.

This story was originally reported by Basketball Network on Aug 7, 2025, where it first appeared.

“I’m grateful I was able to move on before the ship started sinking” – Pippen had no regrets leaving the Bulls after MJ’s second retirement

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