When you think about the Chicago Bulls dynasty, your brain probably goes straight to Michael Jordan hitting a shrug against Portland or flying from the free-throw line. It’s natural. Jordan was the face of the universe. But if you actually talk to the guys who played against those teams, the conversation shifts pretty quickly to the man wearing number 33. Scottie Pippen wasn’t just a sidekick. Honestly, calling him a "Robin" is kinda insulting when you look at how that team actually functioned on the hardwood.
He was the connective tissue. The defensive nightmare. The guy who basically invented the modern "point forward" role while making sure the Bulls didn't implode when MJ was off playing baseball or gambling in Atlantic City.
People love to argue about Pippen’s legacy, especially since The Last Dance came out and made things... complicated. But to understand the Scottie Pippen Chicago Bulls era, you have to look past the scoring titles and the Nike commercials. You have to look at the guy who was arguably the most versatile basketball player to ever lace up a pair of sneakers.
The 1.8 Percent Chance That Changed History
Most people don’t realize how close the Bulls came to never having Pippen at all. He didn't come from a blue-chip basketball factory like Duke or North Carolina. He was at the University of Central Arkansas—an NAIA school—and he started there as a 6-foot-1 student manager. He literally grew five inches in college.
By the 1987 NBA Draft, Jerry Krause (the Bulls GM) was obsessed with him. He saw this lanky, terrifyingly athletic kid who could defend anyone and pass like a guard. Krause pulled off a trade with the Seattle SuperSonics to get him at number five. If that trade doesn't happen, the 90s look completely different. Jordan might have stayed a scoring champion with zero rings.
Why the 1993-94 Season Proved Everything
There’s this weird myth that Pippen was only good because he played next to the Greatest of All Time. That’s just objectively false. When Jordan retired to play baseball in 1993, everyone expected the Bulls to fall off a cliff.
They didn't.
Pippen took over the leadership role and led the team to 55 wins—only two fewer than they’d won with Jordan the year before. He averaged:
- 22.0 points per game
- 8.7 rebounds
- 5.6 assists
- 2.9 steals (basically a human vacuum)
He won the All-Star Game MVP that year and finished third in the actual MVP voting. He proved he could be "The Guy." The Bulls were one controversial referee call away from potentially making the Finals without Jordan. That season is the ultimate proof that Pippen was a superstar in his own right, not just a product of MJ’s shadow.
The Contract: A Seven-Year Nightmare
You can't talk about the Scottie Pippen Chicago Bulls years without mentioning the money. It's the most famous bad contract in sports history. In 1991, Pippen signed a seven-year, $18 million extension.
At the time, he wanted security. He grew up in a house with 11 siblings in Arkansas, and two of his family members were in wheelchairs. He was terrified of a career-ending injury leaving him broke. So, he took the long-term deal against the advice of literally everyone—his agents, his owner, and even Jordan.
As the NBA's popularity exploded and salaries skyrocketed, Pippen became the 122nd highest-paid player in the league. By the 1997-98 season, he was making $2.7 million while Jordan was making over $30 million. That massive pay gap is what fueled the resentment you see in documentaries today. It’s why he delayed his foot surgery until the start of the '97 season—he was basically striking against management.
Defensive Mastery That Stats Can't Capture
If you want to know why the Bulls were a dynasty, look at their defense. Pippen was named to the NBA All-Defensive First Team eight years in a row. Eight.
He was 6-foot-8 with a 7-foot-3 wingspan. He could guard the opposing team's lightning-fast point guard (like he did to Magic Johnson in the 1991 Finals) and then switch onto a power forward in the same possession. He and Jordan would trap players at half-court, and it looked like a scene from a horror movie for the ball-handler.
Pippen led the league in steals in 1995, but his real value was "the ghost." He’d be guarding his man on the wing, see a play developing across the court, and somehow teleport there to block a shot or deflect a pass. He made life easy for everyone else on the floor.
The Complexity of the MJ Relationship
It's sorta sad how things have turned out lately. For years, they were the gold standard for teammates. Jordan called him his "best teammate of all time." Pippen was the guy who carried MJ off the court during the "Flu Game."
👉 See also: Isaac Pitbull Cruz Last Fight: Why That Majority Draw With Lamont Roach Still Stings
But since 2020, the relationship has cratered. Pippen felt The Last Dance was a Jordan propaganda piece that didn't give enough credit to the rest of the team. In his book Unguarded, he was pretty blunt about it, saying MJ was "condescending" and that the teammates were treated like "props."
It’s a nuanced situation. Jordan was a famously difficult teammate who pushed everyone to their breaking point. Pippen was the "good cop" who kept the locker room together. Both things can be true. Without Jordan’s drive, they might not have won. Without Pippen’s versatility and personality, they definitely wouldn't have.
Legacy and Actionable Insights
So, what should you actually take away from the career of Scottie Pippen with the Chicago Bulls?
First, ignore the "sidekick" narrative. In the modern NBA, every team is looking for a "Scottie Pippen"—a long, versatile wing who can defend multiple positions and play-make. He was decades ahead of his time.
🔗 Read more: Why Giants Stadium New Jersey Still Defines North Jersey Sports Culture
Second, the contract situation is a masterclass in why "betting on yourself" became the mantra for modern athletes. Pippen’s frustration changed how players look at long-term deals.
How to Appreciate Pippen Today:
- Watch the 1991 Finals: Look at how he disrupted Magic Johnson. It changed the entire series.
- Look at the 1994 Playoffs: See how he handled being the primary option.
- Study the "Point Forward" Evolution: Understand that guys like LeBron James and Draymond Green are essentially iterations of the blueprint Pippen created.
Pippen finished his Bulls career with six rings, seven All-Star appearances, and a jersey hanging in the rafters of the United Center. He wasn't the "other guy." He was the indispensable guy. If you're building an all-time team, you might pick MJ first, but you’re probably looking for a Scottie Pippen immediately after.
To really dive deeper into this era, your next move should be watching full-game replays from the 1993-94 season. It’s the purest look at Pippen’s individual brilliance when he wasn't deferring to anyone. Pay attention to how he initiates the offense from the top of the key—that's where the modern game was born.
Practical Next Step: If you want to see the specific tactical impact Pippen had, look up the "Full Court Press" highlights from the 1996 Bulls season. Watch how he and Jordan used their length to create turnovers. It's the best way to visualize why he was the most feared defender of his generation.