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When considering Penny Hardaway, it’s always a balance of remembering what was, and pondering what could have been.

From his early days as a prep star at Treadwell High School in Memphis, to his All-American career at then-Memphis State, all the way to his tremendous early tenure with the Orlando Magic, Penny truly seemed to have it all.

He had the immaculate nickname — inadvertently given to him by his grandmother while calling him “Pretty” with a deep Southern accent — not to mention his just-as-cool given name (Anfernee). His talent seemed from the future, meshing smooth point guard skills and off-the-charts athleticism in a 6-foot-7 frame. His tandem with Shaquille O’Neal, an outgrowth of their chemistry while filming the classic “Blue Chips,” was a credible alternative for those not predisposed to the Jordan-Pippen bandwagon.

With all of that in his favor, it’s no surprise Penny was one of the biggest stars of the mid-90’s NBA, with a substantial assist from Nike. His array of signature sneakers was perhaps second only to Michael Jordan’s in esteem, ranging from the iconic royal blue Foamposite to the futuristic Penny 2. The soft-spoken Hardaway wouldn’t seem an ideal corporate pitchman, but much like Jordan with motormouth Mars Blackman, Penny was a flawless straight man as Chris Rock made Lil’ Penny a sensation. And he’s one of the few players in history that can boast Jordan himself wearing his signature sneakers on the court.

Acquired from the Warriors in an epic Draft Day trade for Chris Webber, Penny stepped in as an immediate cornerstone of the Magic. A two-way force, Penny finished second to Webber for Rookie of the Year. He then was named first-team All-NBA in just his second season in the league. The Magic beat the formidable Bulls to make the NBA Finals, where they were swept by Houston despite Penny’s 24 points per game. Still, it seemed as if a potential dynasty was brewing in Orlando.

Despite another first-team All-NBA season for Penny, the Magic were knocked out of the playoffs by the 72-10 Bulls the following year, after which Shaq sought out greener pastures — and somewhat of a Hollywood career — by signing with the Lakers.

“I thought we would at least have one championship, I thought multiple …” Penny told me a few years ago. “Things would have definitely gone different with Shaq staying around and not leaving.”

Ironically, it was only after Shaq departed that Penny’s true potential came to the surface. Though his supporting cast in Orlando was lacking, Hardaway nearly rallied his 7-seed Magic past the 2-seed Heat in the first round with a series of masterful performances. Down 0-2, Penny scored 42 points in Game 3 and 41 in Game 4, both victories. He then scored 33 points in Game 5; the Heat would win, but Penny showed signs of becoming a transcendent NBA player.

But you know what they say about the best-laid plans. Penny injured his left knee early the next season, and though he was still a talented player, he was never quite the same. He would be traded to the Suns in 1999 to team with Jason Kidd, and though they made a solid playoff run that first season, a pair of microfracture surgeries on that troublesome knee would render him a role player for basically the rest of his career, as he bounced from team to team until retiring in 2007.

Penny’s time atop the basketball world was brief, but it afforded him a lasting legacy. Hardaway owns multiple businesses in his hometown of Memphis, helps to promote youth basketball tournaments, invested in a partial stake in the Grizzlies and has become a successful broadcaster. In addition, his popular Nike sneakers not only see retro releases to this day, but new models continually hit the market, helping him remain relevant to a brand new generation.

Mid-90’s NBA fans will always wonder what could have been had Penny’s knees held up. But he’s a living testament to the fact that to dwell on what could have been would be a disservice to what actually was: a significant legacy and following that carries on to this day.

“I never imagined this back when I was playing in the NBA, that my shoe would be going on this long,” Hardaway told me. “I did picture myself having a line of about 15 different pairs of Pennys, because I thought my career would go on that long and it’d be a different shoe every year.

“But still, to have the line still going on, it’s a great feeling.”

Birthday: July 18th, 1971

Height/Weight: 6-foot 7-inches,195 pounds

Twitter: @Iam1Cent

Instagram: @iam1cent

Drafted: 1993, 1st round, 3rd pick, Golden State Warriors (traded to Orlando Magic)




NBA Statistics: 15.2 PPG, 5.0 APG, 4.5 RPG, 1.6 SPG, 0.4 BPG, 45.8% FG, 77.4% FT, 704 games