Everyone knows the Blue Chips story—how Penny Hardaway lit it up alongside Shaquille O’Neal on set and turned their chemistry into more than just a cinematic spark. It tipped the $3.2 billion Orlando Magic’s draft decision in his favor. Chris Webber may have been the projected No. 1 pick in 1993, but Penny used a Hollywood moment to pull off a real-life power move. What most people don’t realize? Shaq wasn’t just cheering from the sidelines—he was drawing a line in the sand. And if the Magic didn’t listen? Let’s just say things could’ve gone nuclear.
Hardaway wasn’t just acting in Blue Chips—he was auditioning for a real role beside the most dominant force in basketball. “Here’s the thing with me,” Penny told The Big Podcast with Adam Lefkoe, “I was extremely smart… I knew Shaq was the most dominant person in the league, and I wanted to play with him really badly because I knew he would make my life easy.” So Penny went all in—every scene, every scrimmage, he fed the big man the ball. “Every time Shaq looks up, every time his head raises, every time his hand is up,” Penny said, “that ball is going to be hitting his hands every single time.” It wasn’t about the script—it was about sending a message. And Shaq? He got the message loud and clear.
Hardaway vividly recalls his first workout with the Orlando Magic while talking to The OGs, and let’s just say it wasn’t the red-carpet treatment you might imagine for a top draft prospect. No entourage, no grand welcomes—just Penny standing there at the airport, completely on his own. Enter ESPN anchor Stuart Scott, who was working in Orlando at the time.
“Nobody was at the airport to pick me up,” Penny recalled. “Stuart Scott picked me up, took me to McDonald’s, and then dropped me off at the arena.” A humble start, to say the least. But the workout? A no-frills session with the strength and conditioning coach. Penny told Shaq about it later, unimpressed by the lack of fanfare: “I was like, ‘Nobody was at the airport.’ And that’s it.”
Fast forward to a pivotal moment: Shaq, who was set on having Penny by his side, wasn’t about to let the Magic settle for Webber. “The Magic was going to take Chris Webber,” Shaq revealed. But he wasn’t about to let that happen. “I went in to talk to Orlando GM John Gabriel and flexed my Superman muscles,” Shaq said, showing his power in the decision-making room. “I told him, ‘I understand you want Webber, but this cat Penny Hardaway is the answer. If you put us together, we could be like Magic and Kareem. If you don’t bring Penny here… then maybe I’ve got to think about doing something else.’”
And that was only the beginning. The second round of workouts was a test. The Magic brought in Anthony Bowie, their top defender, a man who had locked down players like Michael Jordan and Mitch Richmond. Penny was given the challenge: “If he can do well against Anthony Bowie, then you know what he’s all about,” the Magic staff told him. Penny didn’t just do well—he dominated.
“I destroyed the setting,” he said with a grin. “Went back and told Shaq, ‘I destroyed it, bro.’ And the rest is history.” But their run didn’t last as long as it should have.
The burning “what ifs”: Shaquille O’Neal and Penny Hardaway
Unquestionably one of the most powerful teams in NBA history, Shaq and Penny’s tenure with the Orlando Magic is remembered as one of the league’s most significant what-if scenarios. They led the Magic to the NBA Finals in 1995, their first time ever playing on the biggest platform, in just their second season together. In the 1994–95 and 1995–96 seasons, they combined for an MVP-caliber performance, as Shaq and Penny each placed in the top 10 MVP voting rankings. Shaq averaged almost 30 points and more than 10 rebounds a game, and Penny contributed more than 20 points and five assists, demonstrating their exceptional teamwork. Together, they helped the Magic to three straight playoff appearances and made Orlando a bona fide contender in the Eastern Conference.
But then, things got rocky. Shaq’s decision to leave Orlando in 1996 for the Los Angeles Lakers marked the end of one of the most promising duos in NBA history. Reflecting on their split, Shaq admitted that the hardest “what if” in his mind is how many championships he and Penny could have won together…
“I hate to think about ifs,” Shaq said on his podcast, “but the only question that really is at the top of my ifs is how many would Shaq and Penny have won.” He also acknowledged that egos played a significant role in their split, with external pressures causing him to feel like it wasn’t his team anymore. In hindsight, Shaq expressed regret and offered an apology to Penny. “I would like to take the time to apologize to you,” Shaq said. “I probably said some stuff I shouldn’t have said. If I ever did rub you the wrong way…I apologize.”
For Penny, looking back, it was all about the opportunity he had to play with a player like Shaq. “I knew what I had in you,” Penny said. “You were the best I ever played with. You pushed me to the highest level. Whatever I had in me, you brought more out every single night.” Shaq was more than just a teammate to him; he was someone who improved him each time they played together. Penny never took that cooperation for granted, and he recognized its importance. They simply clicked, and during those fleeting, enchanted years, they were unstoppable.
The “what-ifs” are inevitable. It’s simple to see a dynasty that could have competed with any of the NBA’s greatest teams given their combination of skill, chemistry, and athleticism. However, what they could have done, rather than just what they did, is what makes their narrative so compelling.
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