In 1997, Maddie, a high school student at Monte Zion Hill** Academy, decided to enter the NBA draft early, and he dreamed of being next"Pennies"Anfernee Hardaway, but many scouts don't think highly of him. "He is 2.03 meters tall, but his shooting is inconsistent, his contribution on the defensive end is insufficient, and he needs to carry the ball"。However, several NBA executives have spoken highly of Maddie as a potential All-Star, including Toronto Raptors president Isiah Thomas, Chicago Bulls general manager Jerry Krause, and Los Angeles Lakers head of basketball operations Jerry West.
The Raptors have the No. 9 pick, and Thomas got a head start and used that pick to select Maddy. But before the draft, Krauss of the Bulls met with Maddy and told him that he would trade Scottie Pippen in exchange for an advanced lottery pick to pick Maddy, and they traded for the Raptors. "A few days before the draft, I went to Chicago to meet with Jerry Krauss. "Maddie recalled. The thought of being Jordan's teammate made Maddie excited. "I'm looking forward to playing the role of Scotty"Maddie said he admitted that he was still dreaming about how to play with Jordan while he waited for Stern to read his name out in the little green room"With Michael, I can do anything, and I'm willing to make any sacrifice for him. "
However, the deal ultimately failed to materialize. Jordan directly approached Bulls owner Jerry Raindorf and asked him to terminate the trade for Pippen, otherwise Jordan would choose to retire, so Maddy's dream of teaming up with Jordan was shattered.