Tracy McGrady has revisited one of the most intriguing “what-if” scenarios of his early NBA years, revealing in a conversation with Brandon “Scoop B” Robinson that the Chicago Bulls once showed strong interest in acquiring him during the late 1990s and early 2000s, a period still defined by the aftermath of their dynasty.
McGrady explained that former Bulls executive Jerry Krause had a long-standing fascination with his potential before he entered full stardom. He described repeated contact through his representation as Chicago explored ways to bring him into the organization.
“You don’t know the type of obsession Jerry Krause had with me,” McGrady said. “It was ridiculous. He used to tell my agent, Arn Tellem, ‘Krause says he’s coming to get you when you’re a free agent.’”
McGrady added that discussions were not limited to future planning. He recalled that Chicago made attempts to position themselves for a move during key transition periods in his early career.
“He tried to make things happen the night before the draft and again in 2000,” he said.
The most striking element of the discussion involved the rumored framework that would have sent Scottie Pippen out of Chicago in exchange for the young guard, a scenario McGrady addressed with caution and perspective.
“You’re talking about trading a Top 50 player [Pippen] for a rookie who’s not ready,” McGrady said. “It puts too much pressure on an 18-year-old. To be alongside MJ? Not a good look.”
At the time, Pippen remained one of the most accomplished two-way forwards in league history, while McGrady was still developing into the perimeter scorer who would later become a multiple-time scoring champion. The contrast in career stages underscores why such a deal never materialized.
McGrady also connected the Bulls’ interest to a broader pattern of near-moves that shaped his career path. He referenced earlier discussions involving Philadelphia and other franchises, reinforcing how frequently his name surfaced in trade conversations before he reached full All-Star status.
He noted that these situations contributed to a career filled with alternative timelines. “My whole career was a what-if,” he said, pointing to multiple early-career scenarios that never came to fruition.
The Bulls’ reported pursuit sits within the wider context of a franchise searching for a post-dynasty identity after Michael Jordan’s second departure. Any move involving Pippen during that period would have carried major structural consequences for Chicago’s roster direction and competitive timeline.
McGrady ultimately entered the league in 1997 and built his own legacy as one of the most skilled perimeter scorers of his era, while the Bulls transitioned into a rebuilding phase that moved away from their championship core.
