Before they won their first championship in 1991 and established one of the greatest dynasties in sports, the Chicago Bulls underwent years of immense struggles both on and off the court.
From numerous playoff heartbreaks to behind-the-scenes turmoil, the franchise faced major challenges that nearly derailed its iconic legacy. Had those obstacles not been overcome, the NBA's history might have turned out very differently.
Specifically, Michael Jordan 's generational talent was undeniable when he was drafted by the Bulls in 1984. Although he was an unstoppable force that filled the box score with historic statistics, the team was a first-round exit in MJ's first three seasons.
Crucially, when Scottie Pippen arrived at the franchise in 1987, Jordan was already an established superstar who heavily focused on individual dominance rather than team play, where his teammates, including Scottie, claimed he was "horrible to play with."
Because he dominated the hardwood with his presence and playstyle, MJ was scrutinized for being a ball hog, which negatively impacted the rest of the roster. Most notably, the team couldn't form a proper bond with Jordan because of his selfish play.
"To me, our team was always about chemistry," said Pippen. "We never could develop chemistry because of Michael. He didn't believe in his teammates. It was hard for us. We got accused for standing and looking because he would always… do the Kobe."
During Pippen's first years with the franchise, the team's chemistry issues would reach their peak in the playoffs when the Bulls matched up against the Detroit Pistons , where they would lose to the eventual back-to-back champions three years in a row from 1988 to 1990.
In 1989, however, before they lost to the Bad Boys yet again, everything would change when Phil Jackson was promoted from an assistant to a head coach.
When he took over immediately, Jackson introduced the triangle offense, which had the greatest impact on the Bulls' turnaround. Not only did Phil develop a unique relationship with MJ, which underscored the importance of team cohesion, but the triangle also forced him to rely more on his teammates.
"When Phil [Jackson] came, it made all the difference to Michael. Phil convinced him to believe in his teammates, and I think I was the first one Michael really trusted. We didn't have to worry about Michael coming down and pulling up one-on-five. We could just play."
The results were instant. Although they lost to the Pistons in the 1990 Eastern Conference Finals, they pushed the eventual back-to-back champion to seven games. Since then, everybody knew the Bulls were up next, especially when Jordan started to give in to Jackson's team-first system.
In the next year, Chicago swept Detroit when they matched up in the Eastern Conference Finals once again, leaving no crumbs on the table. In the NBA Finals, the Bulls followed up their dominant performance by beating the Los Angeles Lakers in five games.
Michael realized the final puzzle wasn't showing more effort and efficiency, but rather showing more assertiveness in his team.
After that, the dynasty was born, and everything else is history.
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This story was originally published by Basketball Network on Jul 10, 2026, where it first appeared in the Old School section. Add Basketball Network as a Preferred Source by clicking here.
