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.

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.

Warriors head coach Steve Kerr recently offered a rare, in-depth look at the cultural foundation behind Phil Jackson’s famed triangle offense — and it had far less to do with X’s and O’s than most might think.

Appearing on The Glue Guys podcast, Kerr explained that the triangle wasn’t merely a NBA system. Instead, it was a living embodiment of Jackson’s personal philosophy, built on authenticity, connection, and a distinctive cultural influence that shaped every player’s role on the floor.

“He was so smart and so dialed into what makes a team go,” Kerr said. “He’s the only guy I’ve ever run into who built an offense based on a culture. The triangle offense was based on the fact that all five guys touched the ball on every possession.”

“His feeling was that the ball movement connected the group, and that’s why he wanted to run that offense,” Kerr added. “I’d never heard of that before, never made that connection before. I thought you just ran plays. But he was so advanced and brilliant — just an amazing coach.”

That authenticity directly informed Jackson’s basketball philosophy. Unlike most coaches, who designed offenses purely for efficiency or to maximize star power, Jackson’s triangle offense was deliberately crafted to foster unity among his players.

The system ensured that all five players handled the ball on nearly every trip down the court. For Jackson, that ball movement wasn’t just a tactical advantage — it was a means of connecting the group on a deeper, more personal level.

By making sure everyone was involved offensively, Jackson cultivated trust, mutual respect, and a shared sense of purpose. That cultural cohesion proved just as essential to the Bulls’ dominance as the brilliance of Michael Jordan, Scottie Pippen, and Dennis Rodman.

“I’ve often wondered what playing with (Kobe Bryant) would’ve been like. Beside (Bryant), you know? What would we have been like? If playing with (Paul Pierce) was like this, then playing with (Bryant) would’ve been like what?,” Kevin Garnett said, via GQ.

Although Kevin Garnett did not refer to winning more championships, he claimed victory just once, securing the 2008 title with the Boston Celtics. If he had joined Kobe Bryant in LA, he likely would have won more, since the Lakers’ legend captured five championships. His comments highlight the strong legacy Kobe left in the NBA as a symbol of hard work and dedication.

Furthermore, Kevin Garnett said he was close to joining the Los Angeles Lakers. In an interview with Dan Patrick, he explained the reasons why he rejected his arrival to the historic franchise. “What’s disturbing about the whole Lakers situation was just Kobe (Bryant) and Phil (Jackson) at the time. They were at each other pretty bad, and a new situation full of uncertainty wasn’t something that I wanted to get into,” as reported by CBS News in 2011.

How did the Kobe Bryant–Phil Jackson feud start in Los Angeles?

In the 2003-04 season, the Lakers were defeated 4-1 by the Detroit Pistons in the NBA Finals. However, not only did they lose the championship, but it was the beginning of the rift between Phil Jackson and Kobe Bryant. In his book ‘Eleven Rings: The Soul of Success’, the legendary head coach confessed the reasons behind the breakup.

“The Kobe incident triggered all my unprocessed anger and tainted my perception of him… It distorted my view of Kobe throughout the 2003-04 season. No matter what I did to extinguish it, the anger kept smoldering in the background,“ he wrote. In addition, Phil confessed that this incident was very personal to him because his daughter had gone through a similar episode.

Despite Phil Jackson’s departure from the franchise at the end of the 2003-04 season, he returned for the 2005-06 season. During his comeback, both stars reconciled and went on to secure two more championships. Had the Kobe-Phil feud never occurred, there was a possibility that Kevin Garnett could have joined the team, allowing him to play alongside the legendary Kobe Bryant.

In his 2004 book The Last Season, Jackson provided a candid and often scathing look at the Lakers’ 2003–04 campaign, which ended in disappointment despite a trip to the NBA Finals. While the Lakers reached the league’s biggest stage, their season was plagued by dysfunction, inflated egos, and simmering tension. Nowhere was that more evident than in the fractured relationship between Bryant and O’Neal—two generational stars who had previously delivered three straight championships to Los Angeles.

Jackson didn’t hold back in expressing his frustrations. Though he acknowledged the on-court brilliance of both players, his reflections painted a portrait of chaos behind the scenes. O’Neal, Jackson noted, was a dominant physical presence, but also emotionally vulnerable. “For all his bravado, Shaq is a very sensitive, fragile soul who appreciates any sign of tenderness,” Jackson wrote. He emphasized that despite criticism of O’Neal’s perceived lack of durability, few understood the toll of carrying a 340-pound frame night after night.

Still, Jackson admitted to being exasperated by O’Neal’s unwillingness to play through pain and his inconsistent conditioning habits—issues that repeatedly frustrated the Lakers’ coaching staff. For all his size and skill, Shaq’s preparation often lagged behind his potential, creating rifts within the locker room and tension with coaches.

Even as Jackson sought to shield O’Neal from critics, not everyone on the staff was as forgiving. Assistant coach Tex Winter, one of the architects of the triangle offense, frequently clashed with O’Neal. Winter criticized Shaq’s footwork and questioned his coachability, suggesting the All-Star center relied too heavily on dunks and raw power rather than refining his fundamentals.

The tension reached a boiling point during one team film session, when O’Neal erupted in anger, cursing at Winter in front of the entire roster. When Jackson confronted O’Neal about his behavior and urged him to apologize, the center’s response underscored the depth of the discord. “I know I’m not doing the right thing,” Shaq said, “but I don’t give a f***.”

Ultimately, the 2003–04 Lakers represent a case study in what happens when elite talent clashes with unmanageable egos. Despite their skill, Los Angeles fell short of a title that season, and the fallout led to O’Neal being traded to Miami. Jackson’s firsthand account remains one of the most revealing insider perspectives on the volatile nature of NBA superteams.

“This caps off a very maturing season for me and certainly a very educating one. This was by far one of the most trying seasons for me mentally… I’ve had a lot more problems to deal with away from basketball than in past years. They weren’t major problems… my life wasn’t threatened… but it was something different to deal with. I guess that’s why this award is more important and different than the other two years,” Jordan said in 1992, as per the Chicago Tribune.

During the 1991-92 NBA season, Michael Jordan played 80 games for the Chicago Bulls. He averaged 30.1 points, 6.4 rebounds, and 6.1 assists. His all-around performance earned him his third MVP award. This came in the midst of a controversial season where he made headlines off the court as well. One of the notable incidents was when Jordan refused to attend the White House to celebrate the 1992 championship.

When the media questioned him about his absence, he responded sharply. “It’s none of your business,” Jordan said, according to the Chicago Tribune. Later, during media day, Michael provided more context for his actions. He explained that his flight was delayed and that he was not in a good mood. Then, the Bulls’ icon clarified why he chose not to attend the White House visit.

“When the team came to us about going to the White House, I already had plans set and I didn’t feel it was fair to change plans at that particular time…It wasn’t my intention to disrespect anyone, but I’ve seen George Bush before. I don’t think he was different from the last time I met him,” explained Jordan, as reported by The Chicago Tribune.

Phil Jackson praised Michael Jordan’s development in MVP season, as Bulls head coach in 1992

Although Michael Jordan did not match the statistics of his 1986-87 and 1987-88 seasons, he still averaged 30.1 points per game. He became a more well-rounded player, evolving beyond just a scorer. This growth came despite criticism from fans, who argued his performance had dropped compared to previous years. However, his head coach, Phil Jackson, recognized Jordan’s evolution as a player.

“More than ever this year, he deserves it because of what he’s been able to do, take some points off his scoring and figure out how to help this team in different ways, some not even statistical, and become a better player overall than ever before. And still carry us when we have to have him. It’s the most auspicious award that you can receive in this league, and to win it back to back has to be tremendously sweet for him,” Jackson said, via Sun Sentinel in 1992.

In a July 2010 interview with the NBA, legendary head coach Phil Jackson shared a revealing moment. Michael Jordan told him, right after returning from the 1992 Olympics, that Scottie Pippen was the second-best player on Bulls’ roster. That statement came with weight, considering the roster’s talent.

Pippen’s transformation from forward to guard marked a turning point in his career. He embraced the new role with intensity and precision. As a result, he secured his place on the team. Moreover, he became a crucial piece on defense for that legendary squad.

This confession still feels surprising today because the two players never had a strong relationship. Even, Scottie Pippen said Michael Jordan was difficult to deal with, and he revealed they never had dinner together. However, Pippen made it clear they respected each other. Their personal bond was not strong, but their connection on the court told a different story. Both played crucial roles in making the Bulls one of the most dominant teams of their era.

“People knew he (Scottie) was a pretty good sidekick to Michael, but all of a sudden, they were starting to recognize that he was a legitimate star in his own right who had really developed over the prior three to four years. He wasn’t just an active, defensive small forward anymore. He was a player who could excel at three, if not four, positions. He was a real force on our team in that regard and Michael recognized that,” affirmed Jackson to the NBA on 2010.

Scottie Pippen often gets overshadowed by Michael Jordan’s legendary presence on the Bulls’ roster. While Pippen never posted jaw-dropping stats, his versatility and impact on both ends of the floor were undeniable. Even so, his value remains underappreciated. Former NBA player Craig Hodges offered a bold perspective on Pippen’s role, going as far as to draw a surprising comparison to Jordan himself.

“I think he was better than MJ, just from a natural standpoint. You’re 6’7” with the same components, but not only is your right hand big, your left is that big too, you know what I’m saying? And you’re finishing with both equally like that… The difference was the level of confidence coming out. And so much, when we look at it, think about it: if you think about how many guys you played with, so much was given to them that it added to their confidence,” stated on All The Smoke podcast.

Among the most talked-about figures during Jackson’s tenure with the Bulls was Rodman. Known for his eccentric behavior and outspoken personality, Rodman made headlines both on and off the court. His unique way of expressing himself often clashed with NBA norms, presenting a challenge Jackson had to navigate when Rodman joined the team.

Reflecting on that period, Jackson revealed an unexpected insight about Rodman‘s arrival in Chicago. Despite Rodman’s stellar performances with the Detroit Pistons and San Antonio Spurs, his behavior raised concerns at the time.

In the 1997 documentary Reflections of a Dynasty, which featured interviews with Jordan and Pippen, Jackson shared that ahead of the 1995–96 season, he compiled a secret list of seven players he believed could help the Bulls win another championship, Rodman included.

“I put down on paper seven guys who I thought could help us out. He (Rodman) was the seventh at the bottom of that list,” Jackson recalled in 1997, reflecting on one of the most dominant dynasties in NBA history.

Why Jackson put Rodman last on his list

Rodman’s arrival in Chicago generated mixed reactions among fans. Known as much for his controversial behavior as his on-court talent, Rodman carried a reputation that gave many, Jackson included, reason for pause.

“It had nothing to do with his talent,” Jackson clarified, speaking about the list he compiled to strengthen the Bulls ahead of the 1995-96 season. “I didn’t have anything against Dennis. It was simply because of what he brings with him.” Despite those concerns, Jackson would later call Rodman’s signing one of the best decisions of his Bulls tenure.

Jackson also admitted that the trade only went through because it was kept quiet at first. He believed Jordan and Pippen might have opposed it if consulted early. “We would have never made the move without checking first with Scottie [Pippen] and Michael [Jordan],” he said.

How Rodman adjusted to the Bulls

With superstars like Michael Jordan and Scottie Pippen already leading the team, Rodman’s integration into the locker room was no small feat. But Jackson understood what was needed.

“We could handle a distraction and a personality like Dennis,” he said. Rodman proved his value quickly, leading the team with 14.9 rebounds per game in his first season in Chicago.

Rodman’s impact on the Bulls

In just three seasons with the Bulls, Rodman left a lasting legacy. He led the team, and the league, in rebounding during each of his three years in Chicago: 1995-96: 14.9 RPG; 1996-97: 16.7 RPG; and 1997-98: 15.0 RPG.

Rodman played a crucial role in Chicago’s second three-peat, helping the Bulls win NBA titles in 1996, 1997, and 1998. His defensive presence and dominance on the boards were instrumental to the team’s success.

Having coached the best of the best in Jordan and Bryant, Jackson is well positioned to highlight what set them apart. Both players won championships and posted legendary stats, but according to Jackson, there’s one key area where Bryant had the edge over MJ.

Speaking on the Gimme The Hot Sauce podcast two years ago, Jackson pointed to Bryant’s mastery of the Triangle Offense as a defining difference. “He was the focal point, and it was easy to get him involved in that. He feasted on it and was always a proponent of it,” Jackson said.

Jackson added, “But we had to use a variety of actions that created opportunities because the game changed.” With that, he emphasized Bryant’s impact on the Lakers teams of the 2000s, highlighting how the five-time champion led Los Angeles to back-to-back titles in that era.

Jackson reflects on Kobe Bryant’s evolution

Over the years, Bryant’s style of play became increasingly effective, playing a key role in the Lakers’ success. Reflecting on that period, Phil Jackson shared his thoughts on the moment when Kobe proved he had transformed into a different kind of player in the NBA.

“Kobe started out as a guard who facilitated the offense, and he figured it out because he was a brilliant basketball mind,” Jackson said. “He liked playing that role. Eventually, he transitioned to the Michael Jordan wing position, where he did most of his scoring later in his career.“

Jackson’s insights on Bryant’s evolution, and how he handled egos within the team, proved crucial during his second stint as Lakers head coach. With a legendary career on the sidelines, Jackson’s vision and leadership helped shape the direction of the NBA in the years that followed.

Jackson on Bryant’s unique perspective

Thanks to the strong bond forged between Jackson and Bryant, the Hall of Fame coach revealed a unique quality Kobe displayed throughout his career with the Lakers. According to Jackson, Bryant had an ability to perceive things that others couldn’t, something that set him apart from the rest.

“You know how they say dogs can see things humans can’t? Kobe was kind of like my little pocket bully,” Jackson said. “He’d be growling at the staircase, and I’d be looking up like, ‘What’s he seeing?’ Then I’d start thinking, what if there really is something there?”

A defining moment in O’Neal’s career came in the early 2000s. He was in peak form, having already earned MVP honors and a Rookie of the Year award in the 1990s. But one decision from that period remains his biggest regret to this day.

With Jackson as head coach, O’Neal played a pivotal role in the Lakers’ success. He led the league in field goal percentage across multiple seasons and was instrumental in guiding the team to three straight NBA championships from 1999 to 2001. But following that historic run, O’Neal faced a difficult personal decision—one centered around a nagging toe injury.

In his autobiography, Shaq Uncut: My Story, O’Neal opened up about choosing to focus on his toe issues rather than pushing for a potential four-peat with the Lakers. It was during that time that Jackson approached him, and O’Neal later admitted it was the biggest regret of his career.

Shaquille O’Neal reveals the biggest regret of his career

In his book, O’Neal opened up about a pivotal conversation he had with then-head coach Jackson. Jackson urged him to undergo a more serious procedure on his toe to prolong his playing career. “He told me, ‘If you get this done right, you can play until you’re forty.’ I wish I had listened to him,” O’Neal wrote.

“Jackson was pushing me to have the more involved surgery,” O’Neal recalled. “He could tell my toe was so painful and stiff that it was affecting my lift, and I was putting too much strain on the rest of my body.“

Why O’Neal chose a less invasive option

Despite Jackson’s advice, O’Neal revealed the real reason behind his decision. “I was too nervous about being out for six months, especially since the Lakers were stalling on the extension we had been negotiating,” he explained. “So I went with the surgery that would keep me out just three months.”

That decision marked the beginning of the end of his time with the Lakers. It wasn’t just the surgery itself, but the timing of it that played a major role. Looking back, Shaq believes that if he had followed Jackson’s guidance, he could have extended his career by several more years.

Shaq’s final seasons with the Lakers

O’Neal spent only two more seasons with the Lakers following the surgery. Though he remained a dominant presence, his performances didn’t match the towering standards fans had come to expect from him.

After returning to the lineup, these were the stats he posted in his final season in Los Angeles:

• Games Played (GP): 67
• Minutes Per Game (MPG): 36.8
• Points Per Game (PPG): 21.5
• Rebounds Per Game (RPG): 11.5
• Assists Per Game (APG): 2.9
• Steals Per Game (SPG): 0.5
• Blocks Per Game (BPG): 2.5
• Field Goal Percentage (FG%): .584
• Free Throw Percentage (FT%): .490

“That’s the greatest player I ever had, that I could consider the greatest player in the game,” Jackson stated about Michael Jordan in a 2001 interview, making it clear that MJ was the most impressive player he had ever seen, even above his then-player with the Lakers, Kobe Bryant, as well as other past stars.

However, this wasn’t the only time Phil referred to Jordan in such terms. In 2009, prior to the induction of the Chicago Bulls legendary guard into the Basketball Hall of Fame, the coach said: “I don’t think anybody will ever really touch what Michael has done for the game. They may be able to break a record he had or maybe win more championships… But Michael’s image as a player will always stand and his greatness will never be superseded.”

On Jordan’s place in NBA history and sports in general, Jackson was clear. “He was perhaps the most recognizable athlete in the world for a decade,” he stated. “That he brought the game of basketball and the NBA to that level will never be eclipsed.”

Phil Jackson compares Jordan to Kobe

Jackson has the unique distinction of having coached two of the greatest players in NBA history, Michael Jordan and Kobe Bryant. With both, he won multiple NBA championships, giving him the perspective needed to compare their respective strengths.

“One of the biggest differences between the two stars from my perspective was Michael’s superior skills as a leader,” wrote Phil in his 2013 book Eleven Rings: The Soul of Success. “Though at times he could be hard on his teammates, Michael was masterful at controlling the emotional climate of the team with the power of his presence.”

In contrast, Jackson noted about Bryant: “Kobe had a long way to go before he could make that claim. He talked a good game, but he’d yet to experience the cold truth of leadership in his bones, as Michael had in his bones.”

Nonetheless, Jackson has also spoken about the relationship between the two superstars. “I know that Kobe has relied on his conversations with Michael over the years,” he explained. “Michael has been very helpful to him and I know Kobe has a great respect for Michael.”

Jordan’s edge over LeBron James, according to Phil Jackson

One of Phil Jackson’s more recent comments on the GOAT debate came during an interview on the Gimme The Hot Sauce podcast in 2023. There, the legendary coach explained why, in his view, Jordan holds an advantage over LeBron James. “You know, it’s a funny thing, you can’t take anything away from either player. They’re absolutely terrific players,” Jackson began.

“You can only turn to the fact that Michael went to the Finals six times and won six championships. And it’s kind of funny, how many 7-game Finals series did Michael have to go to? He never did, it never happened. We won in six at the most,” Phil added. This marks a significant difference from LeBron, who, despite winning 4 titles, has lost 6 Finals.

“The reality is that the record stands and that’s what happens in careers. The game has changed, and the players have changed. How the game has been played has also changed,” Jackson reflected. “So, you know, take nothing away from either player, it’s still a fact that Michael went to the Finals six times and won six championships.”

Phil Jackson’s remarkable career with the Bulls

Before becoming one of the greatest coaches of all time, Phil Jackson had a successful career as a player. He was a forward for the New York Knicks for eleven years, winning two NBA championships in 1970 and 1973. He later played for the New Jersey Nets, where he finished his career in 1980.

Jackson arrived in Chicago in 1987 as an assistant coach under Doug Collins. However, after two years, he was promoted to head coach, beginning the journey that would elevate him to the pinnacle of the league. With Michael Jordan as the star, supported by players like Scottie Pippen, John Paxson, Horace Grant, and Bill Cartwright, the Bulls won their first three titles between 1991 and 1993.

After Jordan’s brief retirement from basketball between 1993 and 1995, the Bulls rebuilt, keeping Pippen and adding new figures like Dennis Rodman, Steve Kerr, and Toni Kukoc. They went on to achieve another three-peat from 1996 to 1998, which ended with the famous Last Dance.

The Lakers were also successful with Phil Jackson

A year after his time with the Bulls ended, Phil Jackson took on a new challenge: leading the Los Angeles Lakers to a championship after more than a decade without one. He succeeded, securing three consecutive titles from 2000 to 2002 with Kobe Bryant and Shaquille O’Neal. Without Shaq, the Lakers won two more championships in 2009 and 2010.

With 13 NBA championships, two as a player and eleven as a coach, Phil Jackson cemented his place as one of the greatest legends in league history. He is often mentioned as the greatest coach of all time and has been in the Basketball Hall of Fame since 2007.