“The city that I loved, that I got drafted by, they don’t really like me anymore” – Penny Hardaway talks about the toughest moment in his career originally appeared on Basketball Network.
During the course of his six-year tenure with the Orlando Magic, Penny Hardaway believed that he and the organization were meant for each other. He was their guy and the one who represented the organization not just in All-Star events but also in the Olympics. Hardaway was also part of that Magic team that made it to the NBA Finals for the first time in 1995 albeit the loss to the Houston Rockets.
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However, there came a point when both sides experienced an unfortunate divorce and it all started because of Penny’s injuries. According to the former shooting guard, his recurring knee injuries made it impossible for him to return as the same player again, marking the toughest moment of his career.
“Doc Rivers came in and you know how much blood, sweat and tears I gave to Orlando and Doc Rivers was honest with me and said to me, ‘If you stay here, we’re going to have to rebuild your image.’ And I was like ‘Man, I am Orlando. Shaq is gone. Everybody knows me, Shaq and Penny Orlando.’ What crushed me was that he said that ‘We’re going to rebuild your image around here in Orlando.’ And I was trying to play through injury for my team and that moment was just the hardest for me. After that, I said maybe it’s time for me to go,” Hardaway said in his recent appearance on the “Star Struck Podcast.”
Hardaway’s departure
Penny was traded to the Phoenix Suns after the 1998-99 season, but he didn’t turn out to be the franchise player he was close to becoming on the Magic. Despite playing 60 games in his first year in Phoenix, the four-time All-Star’s best years were behind him as early as his seventh season in the league. That was the long-term effect of suffering back-to-back meniscus tears, one of which Penny remembers was because of colliding with Joe Dumars.
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“The city that I loved, that I got drafted by, was the guy, first team All-NBA, Olympian and all that, they don’t really like me anymore because I got injured and that was very hard on my brain,” added Hardaway.
Hardaway admitted that he regrets requesting a trade from the Magic during the summer he departed because he felt he could’ve at least given it a try with Rivers. Instead, the three-time All-NBA awardee felt that he followed his instincts at that moment and that was to leave the city that drafted and honed him into the basketball player that he became.
Penny’s potential was limitless
Had Hardaway not left the Magic, there’s a universe where he and Tracy McGrady could’ve teamed up back in 2000. T-Mac later admitted that Hardaway was one of the biggest reasons why he played in Orlando. This could’ve started a new era in Orlando and made them a marquee franchise again, similar to the ’90s.
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Penny also would’ve given the opportunity to salvage his career in familiar territory under a new coach who still believed in him instead of becoming a journeyman and doing the same thing from one team to another. As a result, Hardaway ended up being one of the greatest “what-ifs” in league history.
This story was originally reported by Basketball Network on Aug 13, 2025, where it first appeared.