In April 2017, I sat down with Charles Barkley for a session on Scoop B Radio Overtime that felt less like an interview and more like a State of the Union for 90s NBA legends. At the time, the basketball world was reeling from two major storylines: the fractured friendship between Barkley and Michael Jordan, and the dramatic ejection of Charles Oakleyfrom Madison Square Garden.
Reflecting on this in 2025—as we watch these titans enter a new decade of their post-playing legacies—Barkley’s “buttoned-up” honesty regarding his best friend and his biggest rival provides a definitive look at the complexity of NBA brotherhood.
Michael Jordan: “I Love Him Like a Brother”
By 2017, the silence between Barkley and Jordan had already stretched several years. The rift, famously sparked by Barkley’s critique of Jordan’s management of the Charlotte franchise, was a wound Chuck didn’t shy away from.
“Aye listen, I love Michael Jordan like a brother,” Barkley told me. “We haven’t spoken in a while, but that doesn’t change how I feel about him. We’re both stubborn, but he’s my brother and he’ll always be my brother.”
In 2025, that silence still largely persists, but Barkley’s 2017 comments underscore the tragedy of the situation. It wasn’t about a lack of love; it was about the collision of Barkley’s professional duty as an analyst and Jordan’s legendary sensitivity to criticism.
Charles Oakley: “He Hates Me, That’s On Him”
The tone shifted significantly when we touched on Charles Oakley. The two power forwards had a physical rivalry dating back to the 90s (including a 1996 preseason fight), and Oakley has never been shy about his disdain for “Sir Charles.”
“We got along, he just hates me and I don’t know why,” Barkley remarked. “I got nothing against Charles Oakley. He hates me, that’s on him. We don’t live together, so it is what it is.”
Looking back from 2025, Oakley’s stance has only hardened, often calling Barkley “fake tough” in more recent interviews. Barkley’s 2017 “buttoned-up” dismissal—refusing to match Oakley’s energy—was his way of staying relevant without getting back into the mud.
The MSG Ejection: A Bad Look for the League
We also discussed Oakley’s February 2017 arrest at Madison Square Garden after a clash with Knicks security. Barkley, usually one to defend former players, took a balanced but firm stance on the optics of the incident.
“It made the Knicks look bad, it made Charles Oakley look bad, but more importantly it made the NBA look bad. It was just unfortunate all the way around.”
2025 Retrospective: The “Three Charleses” Era
Today, the dynamic between Barkley, Jordan, and Oakley remains a focal point of NBA nostalgia. Barkley’s 2017 interview served as a snapshot of a man who had made peace with his truth, even if it meant being “at odds” with his peers.
| Personality | Relationship with Barkley (2017) | The “Core” Conflict |
| Michael Jordan | Estranged “Brother” | Professional criticism vs. Personal loyalty. |
| Charles Oakley | Unilateral Rival | On-court physicality that never died off-court. |
| Charles Barkley | The “Honest” Analyst | Prioritizing the “job” over the “clique.” |
As Barkley told me on Scoop B Radio:
“I’m gonna be honest, and people might not like it, but that’s my job.”
In 2025, that honesty is exactly why Barkley remains the most influential voice in sports media, even if his holiday card list is a little shorter than it used to be.
