The NBA today is thriving in the player empowerment era. Players have more freedom to assert their desires and make decisions, such as where they want to play and who they want to team up with. But this was not always the case back in the 1990s.

Team executives were free to make decisions without much input from players. However, one player who was relentless in wanting to play with a specific teammate was Penny Hardaway. In fact, during the 1993 NBA draft, the talented guard from Memphis was so adamant on proving himself to the Orlando Magic that he called the team up to set up a workout so he could prove himself worthy of their top pick.

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Penny took matters into his own hands

The 1993 draft was bannered by Michigan Wolverines superstar Chris Webber, who was the consensus top pick of that draft class. A highly skilled and versatile 6’10” forward, the Magic’s top executives, led by general manager Pat Williams, envisioned him and the franchise’s cornerstone, Shaquille O’Neal, as the future of the organization.

However, Hardaway had other plans.

While the Magic were set on picking Webber as the first pick, Hardaway desperately wanted to play with O’Neal on the Magic. He took matters into his own hands and reached out to one of the team’s executives, John Gabriel.

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“Hardaway called our personnel guy, John Gabriel, saying, ‘I know you’re not going to take me, but you should. What do I have to do to convince you? What do I have to do? I’ll come back down to Orlando and do whatever you want to prove that I’m you’re best pick,'” Williams recalled.

The call was made on a Sunday and with the draft being held on Tuesday, the Magic was in a bind they had not expected to be in. After much backroom discussion between the Magic staff, they decided to give Hardaway a chance.

“We set up a 5-on-5, hour-long scrimmage with some of our players and some college kids. It was an all-out scrimmage in a church gym. It was just the Magic staff there. And for one hour, Penny just put on a show,” Williams continued.

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Decades have passed since that session, but Hardaway recalled the details like they happened yesterday.

“I remember Anthony Bowie guarding me. He was their best defender at the time, and they had him on me because that was the guy they put on every top two-guard in the league,” he stated. “I think I gave him every move in my arsenal that day.”

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The Magic now had a problem

As convinced as Orlando was in pairing Webber with O’Neal, Hardaway’s final workout sealed the deal. The Magic staff witnessed his undeniable talent and determination and knew that he would be a perfect fit for their team.

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“Just put on a show. Unbelievable. He closed out the last scrimmage with a 3-pointer and looked over at us, shrugged and non-verbally said, ‘Is there anything else you’d like to see?'” Williams said. “We met later that night and said, ‘Oh, boy. What do we do?’ John Gabriel kept saying that the greatest teams have a big man and a great guard. History says that’s the best combo.”

The Magic did pick Webber first overall, but he was traded to the Golden State Warriors for Hardaway in a deal that stunned the rest of the NBA.

The move was widely criticized by the Magic’s faithful, who believed Webber could take them over the top. However, it certainly didn’t take long for Hardaway to change everyone’s mind as he and O’Neal became one of the most dominant duos in the league at that time.

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This story was originally reported by Basketball Network on Sep 21, 2025, where it first appeared in the Old School section. Add Basketball Network as a Preferred Source by clicking here.