Inside Michael Jordan And Scottie Pippen's Complicated Relationship

They say Rome wasn't built in a day, and that certainly applies to the Michael Jordan-led Chicago Bulls dynasty of the 1990s. After all, it took seven years before Jordan, who immediately set the NBA on fire after getting drafted third overall in 1984, won his first league championship. But the Bulls slowly, but surely built around their young superstar guard, acquiring rookies and veterans alike that helped in the organization's transformation. One of those rookies was Scottie Pippen, a 6-foot-7-inch small forward from little-known Central Arkansas who was taken with the No. 5 selection in the 1987 NBA Draft.

Like most first-year players, Pippen came off the bench in his freshman pro season, but by his second year, he had emerged as a key contributor — and a starter — on a fast-rising Bulls team that upset the first-seeded Cleveland Cavaliers in the first round of the 1989 playoffs (via CBS Sports). From there, he would become the Robin to Jordan's Batman, a "point forward" whose playmaking and defense set him apart from the typical NBA three. 

On court, Jordan and Pippen had fantastic chemistry, and that was undoubtedly instrumental to the six league championships that defined the Bulls as the NBA's team of the '90s. However, their relationship off the court has often been contentious, especially in recent years, and it's far more complex than simply saying that these are two legends who went from friends to frenemies thanks to a certain docu-series with a terpsichorean title.

Jordan and Pippen got along well enough on the Bulls

It's a well-known fact that Michael Jordan's competitive streak as a player was off the charts. On a less savory note, he's also been accused of bullying young backup forward Scott Burrell, and he did punch Steve Kerr in training camp ahead of the 1995-96 season — in both cases, the two ex-Chicago Bulls reserves have long since become close friends with His Airness. But how did he get along with the man who turned out to be his most talented teammate during his time in the Windy City?

By most accounts, Jordan and Pippen got along fairly well as teammates, even if there were some times when things got a little tense. As quoted by Fadeaway World, Roland Lazenby wrote in his MJ biography, "Michael Jordan: The Life," that there was one instance where ol' No. 23 didn't show that much sympathy after Pippen skipped practice to mourn the death of his cat. Jordan would also trick Pippen into making losing bets on the Jumbotron animated bull races, as ESPN's Amin Elhassan revealed on an episode of Zach Lowe's "The Lowe Post" podcast (via CBS Sports). But when push came to shove, Jordan had Pippen's back, such as the time when he prevented Bulls general manager Jerry Krause from trading the established star forward for the rights to future star Tracy McGrady on the night of the 1997 NBA Draft, as T-Mac himself claimed in a 2016 interview.

Jordan spared Pippen in his infamous 2009 Hall of Fame speech

When Michael Jordan retired from the NBA for the third and last time in 2003, he was no longer a member of the Chicago Bulls; unthinkable as it was just a few years prior, MJ was a Washington Wizard. Meanwhile, Scottie Pippen called it a career one year later after returning to Chicago for one final season — and a stat line that wasn't anywhere close to the ones he put up during his prime. Still, the pair seemingly remained close in the years following their respective retirements. In fact, Pippen was one of the few noteworthy people Jordan didn't (verbally) dunk on during his now-notorious Basketball Hall of Fame induction speech in 2009 — yes, that same speech that's responsible for the "Crying Jordan" meme that remains popular to this day.

One year later, when it was Pippen's turn to be inducted, he asked Jordan to present him during the 2010 Hall of Fame ceremony. Pippen's speech wasn't anywhere near as incendiary as Jordan's, and with that said, the friendship with his longtime teammate still appeared to be solid. In 2011, Pippen remarked on ESPN Radio that LeBron James had the potential to surpass Jordan as the NBA's greatest of all time, but that didn't trigger any sort of beef. Unfortunately, that would no longer be the case close to a decade later after a certain sports documentary kept basketball fans occupied amid an extraordinary global health crisis.

The Last Dance triggered a feud between the two superstars

The 2020 ESPN/Netflix documentary "The Last Dance" can be considered a celebration of the 1990s Chicago Bulls' status as one of the NBA's greatest dynasties. That said, it was also a celebration of Michael Jordan's greatness as the on-court leader of this Bulls dynasty, and many other former Bulls, Scottie Pippen included, spoke candidly about their glory days winning championships, making it known at multiple points that it wasn't all good times behind the scenes. That candor was evident when Jordan called out Pippen on multiple occasions in the docu-series, describing him as "selfish" for wanting a better contract. (His criminally underpaid status was one of the main reasons he ultimately left the Bulls after their second three-peat.)

Rumors soon began to swirl regarding Pippen's alleged displeasure with his portrayal in the docu-series, with veteran sportswriter Sam Smith telling The New Yorker that he thought Jordan and Pippen's relationship was not in the best of places. Toward the end of July 2020, Pippen denied these rumors, claiming that he and Jordan were going to be "friends forever" during a podcast appearance. But when he spoke to The Guardian in December of that year, he admitted feeling hurt by "The Last Dance" ... while also noting that he and Jordan cleared the air and that all was okay between the pair.

As it turned out, that may not have been the case after all.

Pippen tore into Jordan in his 2021 autobiography

In his December 2020 interview with The Guardian, Scottie Pippen said that "The Last Dance" focused too much on Michael Jordan. He would double down on those comments close to a year later when he published his memoir, "Unguarded." GQ published some excerpts from the book that underscored Pippen's continued unhappiness with Jordan.

"The final two episodes aired on May 17," Pippen wrote. "Similar to the previous eight, they glorified Michael Jordan while not giving nearly enough praise to me and my proud teammates. Michael deserved a large portion of the blame. The producers had granted him editorial control of the final product. The doc couldn't have been released otherwise. He was the leading man and the director."

Pippen also wrote about feeling patronized in the documentary. "I was nothing more than a prop," he complained. "[Jordan's] 'best teammate of all time,' he called me. He couldn't have been more condescending if he tried." He went on to stress that he and his other non-Jordan teammates didn't get the credit they deserved and that the press would keep lionizing Jordan as the perfect basketball player even when he had one of those rare off-nights. 

Beyond "The Last Dance," Pippen threw the "selfish" accusations right back at Jordan, blasting him in the pages of "Unguarded" for his first retirement in October 1993. "You want to know what selfish is? Selfish is retiring right before the start of training camp when it is too late for the organization to sign free agents," he wrote, though it should be noted that Jordan made this decision just months after his father was murdered, leaving him emotionally drained on top of the physical and mental stress he was dealing with as one of the world's most talented — and famous — professional athletes.

The relationship between Jordan and Pippen remains as complicated as ever

With the dust long settled after "The Last Dance" became must-see early-pandemic-era viewing on Netflix, it doesn't seem likely that Michael Jordan and Scottie Pippen will ever bury the hatchet. At least that's how Charles Oakley, who was teammates with the two on the 1987-88 Chicago Bulls, sees it. 

"[Jordan] always praised Scottie, always praised Scottie. He never talked down about him, but I don't know what happened since 'The Last Dance,'" Oakley said in a January 2022 episode of "The Bill Simmons Podcast," per the New York Post. "It seems like things just — he probably said, 'OK, Scottie said this stuff about me. OK, I'm not gonna say nothing.' He's not gonna say nothing back in the press, none of that, try to go back to Scottie. He's just gonna keep doing what he's doing — play golf, fish, relax and smoke cigars."

Still, when he was asked by KTLA just four months later if he would play with Jordan again in any circumstance, Pippen didn't hesitate when giving his answer. "Yes, I want to play with Michael Jordan," the Bulls legend said with a smile. That was just about the extent of the comments Pippen directly made about his former teammate, and it does show that he still has a lot of respect for Jordan's otherworldly skills, though as Fadeaway World pointed out, that's not necessarily a sign that Pippen and Jordan may eventually let bygones be bygones and become friends again.