The connection that Michael Jordan shared with his lifelong friend, Howard H. White, is well-documented. But that’s still the surface of their friendship. MJ was comfortable sharing his deeply personal thoughts with the longtime Nike executive long before they became media bombshells. During an appearance on The Pivot Podcast, White shared a stunning revelation about His Airness’ early career mindset and how he knew that shocking switch to baseball was coming.

White confirmed to the Pivot hosts that long before securing his legendary status, the Chicago Bulls icon was reportedly so consumed by his pursuit of a single NBA championship that he contemplated walking away from basketball entirely once he achieved it. He recounted a private conversation with Jordan that occurred while the superstar was still desperately trying to overcome the “Bad Boys” Detroit Pistons in the late 1980s.

“This before he ever wins the championship. We out in the driveway washing his cars and he says, ‘You know, H, we win this thing this year. You know, I probably quit,'” White revealed to the NFL stars Ryan Clark, Channing Crowder, and Fred Taylor. When asked precisely when this happened, White emphasized it was during the grueling postseason battles with the Isiah Thomas-led Pistons that won the ’89 and ’90 titles.

“He said, ‘Yeah, we win. I probably just quit.’ I said, ‘You give it up?’ ‘Yeah. Yeah, that’d be enough. If we win it, I got that championship. That’d be enough. I probably give it up.'”

It goes without saying but White says it anyway, “Well, obviously that won’t be true. We can see that.”

His Airness led Chicago to its first-ever title in 1991, a feat so big, it turned the NBA into a primetime product on live television. White knew his friend’s mindset well. Instead of walking away after the ’91 title, Jordan’s competitive fire couldn’t end there. He’d go on to win two more titles before making that prediction come true.

White noted that this relentless obsession manifested in everything Jordan did, including his famous 1993 retirement to play minor league baseball with the Chicago White Sox.

“How he went after that. I mean, literally, he changed his entire weight room into like a baseball workout room,” White recalled. “But that’s who he is. Yeah, he’s obsessed with whatever that is.”

White’s speaking of a time Michael Jordan was at his most vulnerable and frustrated professional juncture. Between 1988 and 1990, the Pistons repeatedly eliminated the Bulls from the postseason using their physical “Jordan Rules” defense. Jordan finally broke through in 1991, sweeping Detroit in the Eastern Conference Finals en route to his first of six NBA titles.

There was a time though that White did think MJ would return to the court. However, as the 1994-1995 MLB labor dispute continued, Jordan refused to cross the picket line to the Majors. To Howard’s surprise, Jordan didn’t just announce, “I’m back,” he hit the gym to get back into NBA shape in 1995.

After unretiring in 1995, MJ briefly wore the No. 45 jersey when he lost to Shaquille O’Neal’s Orlando Magic. Nick Anderson famously said that “No. 45 doesn’t play like No. 23.” That slight immediately triggered Jordan’s infamous competitive nature.

“That’s just Michael Jordan. Of course, that probably ain’t the right one to say it to,” White said and the hosts agreed that Jordan’s historic 1995–96 comeback season. “His mentality is winning,” White said about his friend and it fits.