Michael Jordan won six championships in his storied career with the Chicago Bulls, but many wonder if he could have won more. Jordan retired for the second time in 1998, right after three-peating for the second time in the decade. He had gas left in the tank, and a video resurfaced recently where he spoke about chasing another ring.
“Well, you take it year by year,” Jordan said. “I do believe we could have won seven. I don’t want to take anything from David Robinson and those guys, and it’s a shortened year in ’99. But I felt like we still had a good chance if we would have kept the team together.
“Now, that was a big decision from the Bulls’ standpoint,” Jordan continued. “We’ll never know, but it’s great for thinking, great for conversations, great for debating. But in my mind, I really believed we could’ve won seven. And then if we won seven, then our competitive nature would have been, ‘Let’s keep going. Let’s get to eight, let’s get to nine till someone beat us,’ Until I actually lose in the Finals, which never happened.”
Michael Jordan on chasing a seventh ring:
“I do believe we could’ve won seven—we’ll never know, but it’s great for thinking, conversation and debating…competitive nature would’ve been let’s get to eight…until somebody beat us…till’ I actually lose in the finals” pic.twitter.com/cvw5RR0Q0i
— JordanMuse (@JordanMuse_) April 14, 2025
Following Jordan’s second retirement, Scottie Pippen was sent to the Houston Rockets in a sign-and-trade while Dennis Rodman was released. The Bulls cleaned house and have never really come close to winning since.
We’ll never know for sure what would have happened if the Bulls had stuck together after winning the title in 1998. The Big 3 was getting up there in age, and while playing just 50 games in the lockout-shortened 1998-99 season would have been great for them, the schedule was compressed. It’s really hard to gauge what kind of shape they’d have been in when they got to the playoffs.
You’d never completely bet against Jordan, who had just averaged 28.7 points, 5.8 rebounds, 3.5 assists, 1.7 steals, and 0.5 blocks per game in 1997-98 to win MVP. He had upped his scoring average to 32.4 points per game in the 1998 playoffs and was still very much a force of nature. Pippen and Rodman were somewhat in decline, but he wasn’t.
If Jordan had managed to drag the Bulls to the Finals in 1999, he’d have been in for quite a titanic battle there. They would have faced a dominant San Antonio Spurs team led by Tim Duncan and David Robinson. Duncan and Robinson would have given the Bulls’ frontcourt all sorts of headaches, and it would have been a fascinating matchup.
The next year would have provided us with another incredible Finals matchup, as the Bulls would have had to face Shaquille O’Neal and Kobe Bryant’s Los Angeles Lakers. Would they have beaten the Spurs or the Lakers? It’s hard to say.
While Jordan, who was a perfect 6-0 in the NBA Finals in his career, reckons the Bulls would have kept winning, another member of that team does not. Steve Kerr stated he doesn’t believe the Bulls were going to keep winning. He felt the team had lost its edge, energy, and motivation, and was fatigued. Kerr believes the dynasty ended in 1998 because it was supposed to.
