In the 90s, no one could get past them in the NBA: Michael Jordan won six titles with Scottie Pippen. Today the two have nothing more to say to each other.
For decades, the public image of NBA icon Michael Jordan has been shaped by his tireless competitive spirit and almost mythical ability to turn criticism into motivation. All the more surprising is a new revelation from longtime Chicago Bulls chronicler Sam Smith.
According to Smith, Michael Jordan now feels deep regret over the breakdown of his relationship with Scottie Pippen, with whom he won six NBA titles in the ’90s. However, his predominant emotion is not anger, but sadness.
Michael Jordan and Scottie Pippen: At some point their relationship fell apart
In a recent interview with HoopsHype, Smith explained that the estrangement between Jordan and Pippen is less about a fight and more about a broken relationship that neither side has been able to repair.
Smith reported that legendary coach Phil Jackson, who coached both players during the six championships, was “very compassionate towards them [Pippen]” and believed that Pippen “received bad advice.”
Smith then shared a crucial piece of information that changes the tone of the entire story: When Smith asked how Jordan had responded to Pippen’s recent critical public statements, Jackson’s impression was this:
“Michael was really hurt by it and not angry.” Smith added: “He regrets losing that relationship.”
This distinction is significant. In the mythology surrounding Jordan, anger is the familiar emotion – controlled, targeted and productive. Hurt, on the other hand, is different. It suggests that the connection was real and that the breakup took something from him that even victories cannot replace.
NBA legends Jordan and Pippen: A lot of appreciation, but no deep love
Smith’s report also sheds new light on the previous understanding between the two. Even at the height of the Bulls dynasty, Jordan and Pippen were portrayed not as sentimental best friends, but as an uncompromising team – two stars united by ambition and supported by mutual trust.
Smith emphasized that Jordan “really appreciated Scottie” and pointed to Jordan’s Hall of Fame speech as a public example of that appreciation.
“In his Hall of Fame speech, Jordan recognized one player. He specifically mentioned Scottie.”
The estrangement between the two was widely discussed in the years following The Last Dance documentary and Pippen’s subsequent media appearances and memoirs. During this time, Pippen’s criticisms of Jordan, the Bulls, and the portrayal in the documentary became a cultural reverberation in sports.
What Smith offers, however, is not a new round of blame, but a different emotional end point. He described the revelation as “a tender moment” that showed “Michael’s soft side” and reiterated that Jordan’s reaction to the situation was “a sense of loss.”
The NBA loves clear narratives: the alpha player, the deputy, the championship rings, the legacy. But the story of Jordan and Pippen was always more complex than that. Smith’s account underscores the most human truth behind it: Championships can make two people historically inseparable. However, they do not guarantee that they will remain close in life.
