Before injuries altered the course of his career, Penny Hardaway was viewed as one of the league’s future faces. To a generation of fans in the 90s, Penny was more than just a rising star with the Orlando Magic. He was basketball’s next evolution at the point guard position, with his shifty, electric play.
At 6’7”, Hardaway possessed elite passing, athleticism, and unmatched creativity with the ball. He was, in many ways, a player who arrived years ahead of his time. Long before everyone discovered how special he was in the league, though, Grant Hill already knew from playing against Penny during high school.
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“He kind of just came on like right before his senior year. Prior to that, you go all through the camps and the AAU circuit, and you see guys, and you play against them. I remember at the Nike Camp going into my senior year, the summer of ’89, and there’s this 6’7 point guard that’s skinny as a rail and like dominating, and not even scoring,” he recalled.
Revolutionary guard
In today’s NBA, oversized playmakers are everywhere and have become a need for teams in contention. Players such as Luka Doncic, LaMelo Ball and even Cooper Flagg are examples of a new era in playmaking.
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However, in the 90s, the idea of an oversized guard was unheard of, which is why Hardaway was like a unicorn to those who saw him play for the first time, including Hill, who recalls being mesmerized at how he dominated on the hardcourt without even scoring the ball.
At the time, most tall guards were eventually converted to wings or forwards. Penny, however, was a true point guard trapped in a long and athletic frame. He was basically the genesis of why fans loved the likes of Allen Iverson and Kobe Bryant.
“He had all the passes, and the no-look and all of that,” Hill shared. “You didn’t really see that back in the late 80s, right? And you didn’t know who he was. He had it all. I didn’t see the scoring, but he was quick, and he just dominated without shooting.”
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“There was something about him, where looking back, he was that guy. He was the guy,” he added. “Penny was unreal.”
After emerging on the scene in the AAU circuit and becoming a star at Memphis in college, Penny was immediately groomed as a star for the Magic alongside Shaquille O’Neal after the franchise infamously traded away No. 1 pick Chris Webber.
And he wasted no time showing the league why he was the unicorn many whispered about during his early days, averaging 16.0 points and 6.6 assists per game in his first season. By his second, Hardaway was already gaining MVP votes while helping Shaq and the Magic reach the Finals.
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Another what-if story
Ironically, as great as Hill and Penny were, they are ultimately linked with how injuries changed both of their careers. After multiple fairy-tale years as a superstar on one of the best teams in the league, Hardaway would suffer knee problems that slowly robbed him of the explosiveness and athleticism that made him so dangerous. At the same time, Orlando would enter a downward spiral after letting go of Shaq in free agency.
After four exquisite seasons, his body began to break down, making it the toughest moment of his career. Surgeries and recurring setbacks, unfortunately, transformed him from a perennial MVP candidate into a player who constantly tried to rediscover his old form.
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Decades later, Penny is still regarded as a franchise icon and has even carved out a career as a college head coach at his alma mater, Memphis. And despite how many questions linger on what could’ve been if he had stayed healthy and Shaq hadn’t gone to Los Angeles, the reality remains that he was once a special player, one that could’ve ruled the league that wasn’t yet prepared for the likes of him.
This story was originally published by Basketball Network on May 18, 2026, where it first appeared in the Old School section. Add Basketball Network as a Preferred Source by clicking here.