Scottie Pippen’s relationship with his superstar teammate Michael Jordan and former Bulls head coach Phil Jackson has always been complicated. Pippen once admitted he was never particularly close with either of them, a revelation that surprised many given the team’s incredible success together.

Now Jackson has addressed those remarks, revealing that he was stunned to hear how Pippen truly felt about their time in Chicago. Appearing on The Dan Patrick Show to promote “Masters of the Game: A Conversational History of the NBA and Its 75 Legendary Players,” a book he co-authored with Sam Smith, the legendary coach shared his side of the story.

“I was an assistant coach when Scottie came into the league,” Jackson recalled. “I played with him and against him one-on-one and tried to help his game a little bit. I was big in promoting Scottie because, at first, he was coming off the bench. When Doug Collins got thrown out of a game and I had to sub in as coach, the first thing I did was put Scottie in and increase the pressure defense. He was one of the best defensive players to ever play the game, and I had a lot of admiration for him.”

Jackson continued, emphasizing his respect for Pippen’s abilities. “I had a lot of contact with him and always thought highly of his contribution on both ends of the floor,” he added.

Pippen’s personality and Jackson’s perspective

Jackson’s comments also reflected how much he valued Pippen as a player. When he became the Bulls’ head coach, he immediately put more responsibility on the power forward, giving him a larger role within the team’s system. However, from Jackson’s perspective, Pippen’s personality may have prevented their relationship from growing stronger.

“He was the on-court guy I always alerted,” Jackson explained. “Defensive strategies would go through him—double teams, traps, adjustments. I’d blow the whistle and say, ‘Hey, Scottie, it’s time.’ So yeah, it was shocking to hear the comments he made.”

Under Jackson’s leadership, Pippen averaged 19.0 points, 7.1 rebounds, and 5.7 assists per game from 1989 to 1998. He shot 48.4% from the field and 33% from beyond the arc. Yet, his defense truly set him apart—recording 713 blocks and 1,680 steals across 754 games under Jackson’s watch, numbers that helped define the Bulls’ dynasty era.

In a recent interview with Marca, Pippen discussed his time with the Bulls and was asked to compare their legendary 72-10 season in 1996 to the Warriors’ 73-9 campaign in 2016.

Reflecting on the two teams that set the record for the best seasons in NBA history, Pippen suggested that Curry might not have been as successful in the 1990s.

“It depends on the rules. If you play by today’s rules, it’s one thing. But with the rules of the ’90s, Curry would not be the same. If we played in his era, it would be like playing in freedom: nobody grabs you, nobody stops you. I don’t know who would win,” Pippen said.

“We weren’t made to shoot 25-50 three-pointers a game. They would probably win in that sense, because they have two of the best shooters, like Steph and Klay. But we played physical, we defended hard. We made teams score only 75-80 points. Today, that is almost impossible.”

Pippen questions other stars of the modern era

Pippen also claimed that players like Nikola Jokic and Luka Doncic might not have thrived in his era. While he acknowledged Curry’s shooting brilliance in the modern game, he believes the defensive rules of the ’90s would have made it far tougher to develop that confidence.

He didn’t suggest that Curry wouldn’t be excellent, but noted it would have been much harder for him to score from anywhere on the floor. Curry, a career 42.3% shooter from three-point range, has led the NBA in three-pointers made in eight of his 16 seasons. Still, it would be fascinating to see today’s stars compete against those from previous generations.

Pippen has never held back when discussing his feelings about Michael Jordan or Phil Jackson. In a recent interview with Marca, the Chicago Bulls legend admitted that his relationships with both men were never truly close, despite the dynasty they built together.

“It’s never been on the top shelf. That’s the nature of the business. I mean, I was like that with Phil Jackson, but we’re not tight anymore, neither. So it’s just a part of life and cycles that we go through,” Pippen said.

For fans who grew up watching the Bulls’ dominance in the 1990s, the comment may sting. Pippen and Jordan together formed one of the most iconic duos in sports history, winning six NBA championships under Jackson’s leadership. Yet the bond that many assumed was unbreakable has long since faded.

Why there’s no friendship

According to John Salley, who briefly played with both stars, the friendship between Pippen and Jordan ended in 2004. The distance between them became especially evident during and after the documentary The Last Dance.

The series reopened old wounds. Pippen was unhappy with how he was portrayed and criticized Jordan for hogging the spotlight. Their last recorded conversation happened shortly after the documentary aired, and their relationship has remained fractured ever since.

Jackson’s perspective

Phil Jackson, too, has had a complicated relationship with Pippen. While the coach praised his unselfishness and versatility during their championship run, he also acknowledged Pippen’s darker side.

Jackson once described how Pippen could be a model teammate most of the year, but on rare occasions, slip into a “dark place” that affected the entire locker room. Over time, even their bond seems to have faded.

Scottie Pippen has never been shy about sharing his thoughts when comparing basketball across different eras. In a recent interview with MARCA, the Bulls icon admitted he is not entirely convinced that modern-day stars like Doncic and Jokic would have thrived in the league during the 80s and 90s.

“I don’t know if they could dominate. In the 80s and 90s we used to press all over the floor. Could Jokic bring the ball up against such pressure? I don’t know. Sure, he can see the court and pass very well. But I don’t know if he would be comfortable bringing the ball up from the back with that pressure,” Pippen explained.

Pippen’s point holds weight. The intensity of defensive pressure in the 80s was far greater than today, and physicality played a much bigger role. Still, the debate remains open. Would players like Doncic and Jokic struggle in such an environment, or would their unique skills allow them to adjust?

History backs Pippen’s point

History shows that great players tend to transcend eras. Larry Bird is a prime example. He was not the fastest or strongest, but his shooting, vision, and competitive drive made him a nightmare for defenses in the 80s NBA.

If a “slow” Bird could dominate against the physical defenses of the Bad Boys Pistons or the Showtime Lakers, it becomes harder to argue that Doncic and Jokic wouldn’t eventually find ways to impose themselves as well.

The qualities that would make them stand out

Doncic, with his step-back three, 6-foot-7 frame, and ability to control the tempo, has often been compared to Bird for his flair and creativity. In the 90s, he may not have drawn as many free throws, but his footwork and vision would still have created mismatches. His game relies more on skill and manipulation than raw athleticism, making it adaptable across generations.

Jokic, meanwhile, is essentially a 7-footer with the passing vision of a point guard. His footwork, touch around the rim, and ability to exploit mismatches in the post-heavy 90s would have made him a unique weapon. While physical defenders could have tested him, his IQ and versatility suggest he would still have found ways to dominate.

The Bulls captured six titles in eight years, earning two separate three-peats between 1991–93 and 1996–98. While Pippen was essential to those runs, Parish credits Dennis Rodman as the difference-maker behind Chicago’s dominance.

“Let’s not forget. Chicago wouldn’t have won s— without Dennis Rodman. I don’t care how good Michael and Scottie Pippen were, they wouldn’t have won s— without Dennis Rodman,” Parish said during an appearance on The Coach JB Show with Big Smitty. “Because Luc Longley, and that other m—, I can’t think of the other center’s name, they was just in the way”.

“If it was not for Dennis Rodman, defense and rebounding, which we all know wins games, wins championships—defensive rebounding, and keeping turnovers in check—Chicago wasn’t winning s— without Dennis Rodman,” he continued.

Before joining the Bulls, Rodman was a key part of the Detroit Pistons‘ “Bad Boys” era alongside Isiah Thomas, helping the team win back-to-back NBA titles in 1989 and 1990—eliminating Jordan and the Bulls along the way.

Rodman’s tenure with the Bulls

Rodman arrived in Chicago for the 1995–96 season, and his impact was immediate. The Bulls jumped from a 47–35 record to an NBA-best 72–10, a mark that stood until the 2015–16 Golden State Warriors surpassed it.

A two-time Defensive Player of the Year (1989–90, 1990–91), Rodman brought exactly what the Bulls needed on defense following Jordan’s return from retirement, that led Chicago to their second three-peat.

He led the NBA in rebounding for seven consecutive seasons and routinely battled the league’s most dominant big men, including Shaquille O’Neal, Karl Malone, Alonzo Mourning, and Charles Barkley.

Scottie Pippen and Michael Jordan’s relationship has been notoriously turbulent in recent years. The former Bulls stars have exchanged barbs in public, fueling a feud that continues to captivate fans and pundits alike. Still, their complicated history doesn’t erase the bond they once shared during the franchise’s golden era. At least back in 2010, the respect was mutual—and public.

That year, Pippen was inducted into the Hall of Fame and selected Jordan, who had been inducted the year prior, to formally present him. The gesture reflected the significance of their shared journey and was a continuation of a Hall of Fame tradition in which past legends present new inductees. It was a moment of reverence, not rivalry—fitting for a duo that won six NBA titles together.

“I can’t think of a better person to do it,” Pippen said at the time, via ESPN. “Michael is someone I shared my career with, accomplishing most of what I have accomplished thus far.” Their paths were intertwined, and for one evening in Springfield, Massachusetts, the narrative turned from division to tribute.

Pippen’s heartfelt words for Jordan

Despite the tension that has developed in recent years, Pippen’s speech that night revealed the deep respect he once held for Jordan. Their legacy wasn’t just about championships and accolades. It was about two competitors pushing each other to greatness and forming one of the most iconic partnerships in NBA history.

“Michael was a great teammate, teacher, and admirer,” Pippen said during his speech. “I’m excited to have an opportunity to be the first person that he has presented into the Hall of Fame. I figure if anyone deserves to be on the stage with me, it’s him.”

Pippen continued, “What an honor it is for me as a basketball player to have the all-time great presenting me here tonight. It was so valuable to me as a player to see someone who had the same desire, determination, passion, and love for the game.” He concluded his remarks with a message that still resonates with Bulls fans. “MJ, you have touched so many people’s lives, but none like mine. Thank you for being the best teammate. I will always cherish that experience and our relationship forever.”

Why not Dennis Rodman?

While Pippen and Rodman shared three championships with the Bulls, their relationship was more functional than sentimental. Before teaming up in Chicago, they had been fierce rivals—most notably during Rodman’s time with the Detroit Pistons. Pippen wasn’t initially thrilled when the Bulls acquired the controversial forward, but he eventually came to respect Rodman’s value on the court.

Rodman’s relentless defense and rebounding were crucial to the Bulls’ second three-peat, but the emotional connection between Pippen and Jordan was on another level. For Pippen, the Hall of Fame moment was personal, not just professional. And in that context, there was no other choice. It had to be Jordan.

Kerr had arrived in Chicago that summer from the Orlando Magic and found himself in a very different environment from the one the Bulls had enjoyed in previous seasons, during which they had captured three straight championships. In that context, Pippen was no longer the second option—he had become the team’s leader.

“I think he felt a lot of pressure to replace Michael, and obviously, nobody could ever do that,” Steve recalled in an interview shared by Grantland in 2013. However, the guard highlighted Pippen’s performance that season. “If you remember, he had an MVP-caliber year. He was unbelievable that season, probably his best season ever.”

Indeed, during the 1993–94 season, Scottie posted some of the best numbers of his NBA career. He played 72 regular season games, averaging 22.0 points, 8.7 rebounds, and 2.9 steals per game—all career highs in those categories. That year, the forward was also named All-Star Game MVP and finished third in the voting for league MVP.

The moment things spiraled for Pippen

Led by Pippen, the Chicago Bulls finished third in the Eastern Conference with a 55–27 record. That earned them a trip to the playoffs, where they easily advanced past the first round by sweeping the Cleveland Cavaliers. However, in the semifinals, they ran into the New York Knicks, and that’s when things got complicated.

In Game 3, with the Knicks up 2–0 in the series and just 1.8 seconds left on the clock in a 102–102 tie, head coach Phil Jackson drew up a play designed for Toni Kukoc to take the final shot. Believing he should have been the one to take that responsibility, Scottie reacted with fury.

As a result, Pippen made the shocking decision to stay on the bench and not go back onto the court for those final moments. Kukoc hit the shot and the Bulls won that day, but Scottie’s decision didn’t go unnoticed—even among his teammates, who felt deeply disappointed.

Kerr reflects on Pippen’s reaction

Years later, Steve Kerr looked back on what happened. “In the playoffs, I think in that game, we had a blown 20-point lead in the fourth quarter. Those are the kinds of games Michael would have single-handedly taken over, and I think Scottie probably felt some pressure to do that,” the guard began.

“I’ve said many times it’s such a shame because, in many ways, it ruined Scottie’s reputation, and people who don’t know him might just think of that play and say, ‘Oh man, that guy’s selfish,’” Kerr added. “But he was one of the most beloved teammates in that locker room, and that spans every Bulls team, from the beginning of his tenure there until the end.”

Despite that incident, Steve Kerr has consistently praised what Pippen meant to him and to the Bulls during those years. “Scottie would score four points and dominate the game,” Kerr said in 2010. “That’s what made him one of the best to ever play the game.”

Pippen sees shades of his own style in 23-year-old Thunder forward Jalen Williams. But rather than limit the young star with comparisons to his own legacy, the Hall of Famer said he believes Williams could surpass him. Speaking to ESPN’s Tim MacMahon, Pippen emphasized how the evolution of basketball—particularly in offensive freedom—has created more opportunities for players like Williams to thrive.

“I don’t even want to put a cap on him and say that he’s going to be me,” Pippen said. “I see him being greater, if I can say that. Just because of where the game is today. They have offensive freedom. We didn’t have that; we mostly ran out of a system. Players that are playing in today’s game have a better chance to be better than players in the past because of the ability to shoot the ball. If this kid continues to shoot the three-ball the way he shoots it, I’m not going to sit here and argue with nobody and say that you can compare us. Because you can’t. He wins.”

Pippen’s praise wasn’t just about skill—it was about style. The six-time NBA champion said he sees similarities in how both he and Williams impact the game on both ends of the floor. And while Pippen is already enshrined as one of the greatest two-way players in league history, he acknowledged that Williams’ trajectory, especially in today’s NBA, may put him in a class of his own.

Williams, now in his second full season, has emerged as a cornerstone of a young Thunder squad that has stormed into the NBA Finals. Long before he became one of the league’s most promising stars, he was a student of the game, watching hours of old highlights from the Bulls’ dynasty. Though he was born years after the Jordan-Pippen era, those clips helped shape his understanding of basketball greatness.

In particular, Williams paid close attention to how Pippen and Jordan moved without the ball, played lockdown defense, and dictated tempo without always filling up the box score. It’s no coincidence that Williams’ game reflects a similar all-around polish, one built on defensive instincts, playmaking ability, and unselfishness on offense. Even in a league now defined by pace and space, those fundamentals remain valuable—and they’ve helped him earn the respect of a legend.

Pippen’s endorsement feels like a full-circle moment. For Williams, being compared to Pippen is already a high honor. To receive that comparison directly from Pippen himself—along with a suggestion that he could become even better—is the kind of validation few players ever experience. It speaks not just to Williams’ skill, but to his poise and maturity at such a young age.

As the Thunder continue their championship push, Williams is proving that he belongs on this stage. And if he continues on this trajectory, there may come a time when comparisons to Pippen are no longer about potential—but about legacy. For now, the NBA world is watching closely, and so is one of its greatest small forwards of all time.

Over his illustrious career, Harper collected five NBA Championship rings, three with the Bulls and two more with the Lakers, granting him the rare privilege of having competed alongside some of the greatest players in NBA history like Kobe or O’Neal. It’s this unique perspective that empowers him to deliver insights into discussions surrounding the all-time greats.

Recently, Harper opted not to join the perennial “Greatest of All Time” (GOAT) debate. Instead, he shared his personal starting five drawn from the array of Hall-of-Fame-caliber teammates, like Pippen or Rodman, he played with during his 15-year NBA career. During a recent conversation with The Makeshift Project on Instagram, Harper revealed his all-time greatest teammates lineup.

Given his illustrious career and the iconic figures he shared the court with, determining his all-time starting five might seem straightforward. Unsurprisingly, the lineup boasts some of basketball’s brightest stars, like Rodman or O’Neal, highlighting Harper’s legendary cohorts.

All-time teammate starting five:

• Point Guard (PG): Scottie Pippen
• Shooting Guard (SG): Kobe Bryant
• Small Forward (SF): Michael Jordan
• Power Forward (PF): Dennis Rodman
• Center (C): Shaquille O’Neal

Harper’s choice for Sixth Man: Toni Kukoc

When asked about his choice for the sixth man in an all-time starting lineup, Harper didn’t hesitate to highlight a name less frequently mentioned by former players but worthy of Hall of Fame recognition: Toni Kukoc.

Notably, Kukoc was awarded the Sixth Man of the Year during the 1995-1996 season as part of the Chicago Bulls’ championship team. Sporting the number 7 jersey, the Croatian standout made history with his remarkable contributions to the Bulls’ three-peat triumphs from 1996 to 1998. Although he started in only 22 of the 45 playoff games during those years, his impact was crucial to securing the championship titles.

Harper’s head coach selection: Phil Jackson

Reflecting on his illustrious career with the Bulls, achieving a three-peat, and subsequent success with the Lakers, securing two consecutive titles, Harper confidently chose Phil Jackson as the head coach for his dream team.

Jackson’s unparalleled influence in the NBA has solidified his reputation, with countless former players attesting to his standing as the greatest coach in NBA history.

In a 2023 interview, Thomas named his top three defenders of all time, including two former Chicago Bulls stars and one of the greatest two-way centers in league history. While he claimed he wasn’t ranking them, Thomas has previously gone on record stating that Scottie Pippen tops his list as the best defender in NBA history, with Dennis Rodman coming in second.

“As a defender, he doesn’t get enough credit,” Thomas said on the ALL THE SMOKE podcast. “When we talk about the greatest and best defenders that have ever played in the NBA, Chicago had two of them — Rodman and Scottie Pippen.”

“Scottie was different,” Thomas continued. “At his best, I may have to say that he and Rodman were the one-two best defenders to ever play the game. I want to give him his respect and his props. And then, as a facilitator, Scottie — he was the real deal.”

Thomas vs Pippen: A storied rivalry

The rivalry between Isiah Thomas and Scottie Pippen took shape in the late 1980s, when the Detroit Pistons and Chicago Bulls became perennial Eastern Conference contenders. As the fiery leader of the Pistons, Thomas personified the physical, confrontational style of basketball that defined the era and often frustrated the rising Bulls, led by Michael Jordan and supported by a maturing Pippen.

Those postseason battles were nothing short of legendary. Detroit’s “Jordan Rules” didn’t just target Jordan—they also tested Pippen’s resilience. The Bulls forward, still emerging as a star, took repeated hits from Detroit’s bruising defense, both physically and psychologically. Thomas, never shy in front of a mic, frequently questioned Pippen’s toughness and leadership compared to Jordan, fueling a personal and professional feud that has lingered long after their careers ended.

Rodman’s complex connection with Thomas

Dennis Rodman’s relationship with Thomas was more layered. Originally teammates on the Pistons, the two helped shape Detroit’s identity as the NBA’s most feared defensive unit. Rodman’s energy, versatility, and defensive prowess complemented Thomas’s leadership during their back-to-back title runs in 1989 and 1990.

However, Rodman’s eventual move to the Bulls in the mid-1990s complicated their legacy. By joining Chicago — the very franchise Detroit had built its identity around defeating — Rodman became part of the dynasty the Pistons once stood against. The dynamic shifted, and while mutual respect remained, the symbolism of Rodman wearing a Bulls jersey stung for many Pistons loyalists, including Thomas.

More than a rivalry — a cultural divide

Despite moments of mutual respect among all three players, personal pride and competitive fire have long fueled the tension between Thomas, Pippen, and Rodman. For Thomas, the Pistons’ legacy — one forged in sweat, defense, and defiance — is too often overlooked in favor of the flashier narratives surrounding the Bulls dynasty. He continues to be a vocal advocate for what Detroit represented during its golden years.

Their rivalry was more than physical — it was deeply cultural and symbolic. It wasn’t just about winning games; it was about defining eras, identities, and ultimately, greatness. And for Isiah Thomas, those matchups — and those defenders — are etched into NBA history with the intensity they brought to every possession.

“I’ve been looking at uh Jokic and it’s like… I think we’ve all missed out on how great this guy been the last two years…When I watched this guy play, I can only say, like — How do the best player in basketball not get picked in a pickup game? I’m like wow,” stated Scottie Pippen in a talk with Stacey King in 2023.

Although those comments were made some time ago, Nikola Jokic has only improved his performance since then. This 2024–25 season was the first in his career where he averaged a triple-double. Moreover, he stood out despite major challenges. The head coach Michael Malone was fired just weeks before the postseason began. In addition, the roster showed clear signs of struggle. Even so, Jokic helped push the team to a Game 7 against one of the league’s best: the Oklahoma City Thunder.

Nikola Jokic is already 30 years old and has just one NBA championship to his name. With his prime years in full swing, the Denver Nuggets face mounting pressure to build a stronger, more reliable roster around their franchise star. While Jokic continues to deliver elite individual performances, the team has consistently fallen short of matching his level of play.

During the postseason, he lacked consistent support from his teammates, a key factor in Denver’s inability to make a deep playoff run. Nikola himself has acknowledged that changes are necessary if the Nuggets hope to contend for another title.

According to Sam Amico, the Denver Nuggets have no plans to part with their core championship players. That group includes Jamal Murray, Aaron Gordon, Michael Porter Jr, Christian Braun, and, of course, Nikola Jokic. This stance shows the team’s commitment to continuity and long-term success.

However, the Nuggets still need to bolster their roster. They aim to stay competitive in a tough Western Conference. Yet, without the option to trade any core players, adding a major piece becomes difficult. Therefore, the front office must explore creative solutions to strengthen the roster without disrupting the team’s core project.