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Penny Hardaway Shoes: A Full Timeline

It is hard to encapsulate who Penny Hardaway was, what he meant to basketball in the mid-90s, and, unfortunately, what he could have meant for basketball history. 

In an era dominated by the Chicago Bulls and the ultra-competitive Michael Jordan, Penny and the Orlando Magic felt like the perfect team to dethrone the all-powerful Bulls. The Magic were young, fun, and dynamic. They were led by Penny and a young Shaquille O’Neal. Their solid core of role players included a scorned Horace Grant, who’d left the Bulls to join the Magic. And there was just something poetic about the clash of the blood-red uniforms of the bulls and the electric blue of the Magic. 

Then there was the contrast between Mike and Penny. Michael Jordan was like the terminator: precise, effective, and ruthless. Penny on the other hand was fun, herky-jerky, and versatile. He never seemed to be as bloodthirsty or have the killer instinct that Michael did. But he and the Magic were able to win with their own distinctive style. 

They had a similar vibe to the Golden State Warriors in the early years of their dynasty. It felt like the new, 90s version of the Bird vs Magic rivalry. And if Penny avoided injuries, that just may have been the case. 

Penny Hardaway Shoes: A Full Timeline

Penny Hardaway Shoes: Memphis Tigers

Penny played college ball at Memphis State (now known as the University of Memphis), and now serves as the men’s basketball head coach. He was impressive right out of the gate. Hardaway displayed a level of versatility on the court rarely seen before. He was a lanky 6’7”, 195-pound combo guard who could handle, pass, rebound, score in bunches, and put anyone on a poster (or whatever the expression is these days). Penny averaged 20 ppg, 7.7 rpg and 5.9 apg over two seasons with the Tigers. 

During his college years, Penny rocked Converse. The Converse Accelerator RS1 Hi-Cut to be exact. These guys are some of the bulkiest kicks you’ll ever see. They featured React cushioning. Not React Foam but React Juice (not kidding) which was supposed to offer waterbed-like cushioning as you play.

Penny Hardaway Shoes: Orlando Magic 

Penny joined the Magic in 1993, chosen 3rd overall in the NBA Draft behind Chris Webber and Shawn Bradley. He was then traded by the Warriors to the Magic in a massive deal for number one pick Chris Webber. Penny took to the NBA like a fish to water. He would end up averaging 16 ppg, 5.4 rpg, 6.6 apg and 2.3 spg over an 82-game season. 

Penny was lucky to have entered the NBA at an excellent time. MJ had just retired before the start of the 1993-94 season, which left the Eastern Conference wide open and the NBA hungry for a new superstar. Enter Penny Hardaway.

During his rookie season, Penny rode two iconic early 90s Nike Basketball silhouettes all the way to the Playoffs: the Nike Air Swift (also a favorite of Scottie Pippen) and the Nike Air Prevail. Penny wasn’t the only guy to get his hands on the Prevail in the NBA. Gary Payton and Reggie Miller used the Prevail as their go-to that season and were featured in an absolute classic series of Nike ads 

Nike Air Swift

Nike Air Prevail

He would even lace up a pair of the Air Jordan 9 in a Penny PE:

Air Jordan 9 Penny Hardaway PE

Blue Chips

During his second season with the Magic, Penny became a household name. After starring alongside teammate Shaquille O’Neal in the classic hoops film Blue Chips, he improved his regular-season averages to 21 ppg, 4 rpg and 7 apg. He would be named to the All-Star team and make it all the way to the NBA Finals, where the Magic would face the Houston Rockets. The Magic would ultimately come up short, but Penny solidified himself as “the next guy”. 


During the filming of the movie, Penny wore one of the greatest Penny Hardaway Shoes, the Reebok Pump Vertical

Reebok Pump Vertical

Sneakerwise, Penny had an eventful season. He would rock three Nike models that year: the Nike Air Lambaste, the Nike Air Go LWP, the Nike Air Up, and the first unofficial pair of Penny Hardaway shoes, the Nike Air Flight 1.  

The Air Flight 1 wasn’t technically Penny’s signature shoe. But at the same time, it kinda was. The shoe featured heel and forefoot air, a great fit, and a funky bubble design. The model was worn by several players around the NBA. They were most famously laced up by Michael Jordan himself after he returned to the NBA, during a playoff game that season against Penny and the Magic. 

They were the only shoe Michael would ever lace up in his NBA career that wasn’t his own, which is quite an honor. 

Nike Air Flight 1

Nike Air Go LWP

During the 1995-96 season, Penny and the Magic kept rolling. Penny had his best statistical season, and the Magic made the playoffs, where they met the Bulls on their way to their first championship or their second three-peat. Penny was again named an NBA All-Star and got his first signature sneaker, the Air Penny 1


Nike Air Penny 1 

The Air Penny 1 was the first of Penny Hardaway’s shoes to be an official signature and an instant classic. Designed by Eric Avar (the creative mind behind the Kobe signature line), the shoe offered a heel 180º airbag and a forefoot Zoom Air unit, great traction and support, and was perfectly geared for large mobile guards. The characteristic panels on the side of the shoe offered added containment and represented eagle wings. 

But maybe most importantly, the Air Penny 1 introduced Lil’ Penny to the world. There have been some classic sneaker ads over the years, but the commercials with Lil’ Penny (voiced by Chris Rock) are some of the best ever, hands down! 

That summer, Penny would keep his hot streak alive by winning gold during the 1996 Olympics in Atlanta. We also got a weird pair of Penny Hardaway shoes. Curiously, during the Olympics, he laced up the Nike Flight Zoom 96 instead of his newly-released signature shoe. 


Nike Flight Zoom 96 

As quickly as success had come to Penny, it vanished with the same rapid speed.

After a period of friction with teammate Shaquille O’Neal, Shaq would end up signing with the LA Lakers leaving Penny in Orlando to try and conquer the East single-handedly. 

The one bright spot of that season was that Penny would get his second signature shoe, the Air Penny 2, a great on-court performer, and one of the best looking pair of Penny Hardaway Shoes. The shoe offers a fluid ride, with tons of support and durable materials. But the main highlight of the Air Penny 2 is the cushion. It features a light foam midsole that houses a forefoot Zoom Air unit and a heel airbag. For the second time, Eric Avar was able to create a unique signature model that fit Penny’s image perfectly. 


Nike Air Penny 2

Nike Air Foamposite 1

During that season, Penny would bring us another little piece of sneaker history when he laced up the Air Foamposite 1 just two games before the playoffs. While creating the Air Penny 3, Avar had shown Penny a series of silhouettes to choose from. Penny was famously unimpressed with the options, but saw the Foamposite in a bag and insisted that that be the next pair of Penny Hardaway shoes. 

The Foamposite 1 had been intended for Pippen, but he turned them down so they were given to Penny. But Penny wasn’t actually the first player to debut them on court. This honor fell to Mike Bibby of the Arizona Wildcats, who wore them during Arizona’s run to the NCAA championship in March 1997. 

Penny would stick with Foamposites during the playoffs, famously having to use a Sharpie to color in black lines on the shoe and make it comply with the on court NBA dress code. The Magic would fall to the Miami Heat in the first round that year. From there, things only got worse. 

Penny sat out 63 games of the 1997-98 season with a torn meniscus in his left knee. This injury would start the decline in Penny’s on-court performance.


Nike Air Penny 3

That season Penny wore the Air Penny 3. This Penny Hardaway shoe was (and technically still is) an excellent on-court performer, perhaps the best of the line. Due to injury, Penny never put it through the rigors of an 82 game season but it’s still a beast nonetheless. This shoe delivers solid traction, a full forefoot Zoom unit, a 180º airbag in the heel, and excellent support.

Nike Air Penny 4 

Penny would play one last season with the Magic in one of the most excellent pairs of Penny Hardaway shoes in the Penny line, the Air Penny 4. The Penny 4 wasn’t a fantastic on-court performer primarily due to the shoe’s traction, which was, at best, inconsistent. The rest of the shoe is pretty solid, though and offers excellent support and cushioning with the usual Penny cushioning setup. This would be the last signature shoe that Nike would release while Penny was an NBA player.

Penny Hardaway Shoes with the Phoenix Suns, New York Knicks and Miami Heat 

Penny would go on to play for the Phoenix Suns, the New York Knicks, and the Miami Heat, before retiring in 2008. During this time, he would remain a Nike athlete and rock a bunch of different models including the Nike Air Flight Determination, the Nike Zoom Huarache 2k4, the Nike Zoom Flight 2k3, the Nike Air HowsYaGame, the Nike Zoom Flight Turbine 2002, the Nike Air Flight Determination, the Nike Air Zoom BB, and a bunch of different Shox models. It was almost as if his inability to find a go-to pair was due to his lack of physical comfort on the court.

Other Penny Hardaway Shoes 

After Penny’s retirement, Nike released 2 more signature models under the Air Penny line: The Air Penny 5 and the Air Penny 6, and 1 Penny-inspired remix model, the Nike Air Zoom Rookie. All of these models were released as lifestyle models, though the Penny 5 and the 6 can be used on court.


Nike Air Penny 5

The Air Penny 5 in particular was an excellent on-court model. They featured excellent traction, a seamless fit that offered phenomenal lockdown from heel to toe that kept your foot perfectly contained, and a blend of old school and new school materials. The cushioning on the shoe was also above average, although Nike didn’t include the forefoot Zoom unit that sneakerheads had become accustomed to in Penny Hardaway shoes. 

Nike Air Penny 6

The Air Penny 6 did a great job of paying tribute to the OG signature Penny Hardaway shoes. The Penny 6 looked performance-ready and featured a Posite wing for custom fit and support like the Penny 3, heel Max Zoom, Dynamic Flywire, and decent traction.

They haven’t been seen much on court. There’s an obvious reason for that. 


Nike Air Zoom Rookie

The Nike Air Zoom Rookie was a mash-up model with a bit of Penny flavor added in. The shoe took design cues from the Air Flight 1, the Nike Air Foamposite 1, and the Nike Air Go LWP and blended them into an awesome-looking pair of Penny Hardaway shoes. Emphasis on the “looking”. On court, they were a letdown with lackluster performance features and downright terrible cushion. 

Lil Penny’s Signature line

The last shoes to mention in the Penny universe aren’t technically Penny signatures, and at the same time, they aren’t. The Nike Air Half Cent and the Nike Lil Penny Posite were models Nike put out that were supposedly Lil’ Penny’s signature shoe. Yes, that’s right, the puppet. 


Nike Air Half Cent

Nike Air Half Cent was an awesome mash-up of all the OG signature Pennys featuring highlights of each model. They featured a visible air sole unit in the heel, taken from the Penny 3, the traction was a seamless blend of the Air Penny 2 and the Foamposite 1’s traction patterns and a Foamposite upper. The upper used design hints from the Air Penny 1, the Air Penny 2, Air Penny 3, and the Foamposite 1 themselves. Almost the perfect hybrid.

Nike Lil Penny Posite

The Nike Lil Penny Posite, on the other hand, took inspiration from the Nike Air Go LWP and the Nike Air Up, both models that were not technically Penny signatures. The shoe featured a Hyperposite upper with a Lunarlon midsole and a small heel Zoom unit. The materials were excellent and very similar to the Nike LeBron 11, which was released the same year. The traction was very similar to that of the Air Penny 5. 

The Penny Posite did a good job of creating a futuristic feeling Penny hybrid, but they were by no means an on-court performer. The beefy materials used on the upper made for a restrictive and even painful ride, and the minimal cushioning and inconsistent traction didn’t help. It’s best used only as a lifestyle model. 

Penny was, for a brief period of time, one of the best and coolest players in the league. His signature line is iconic. If only the Penny era had lasted longer!

Let us know what you think. Did we leave anything out? Is there another shoe that you’d put on the list?  We look forward to hearing from you on Twitter, Instagram, or our Discord community.

1 comment
  1. GREAT ARTICLE!! Well-written (becoming rare these days…) and detailed enough where i’m sure even the most hardcore of Penny fans would have learned something new…

    Great to get a true sense of what Penny wore during his career as opposed to just “Penny Hardaway shoes”… if that makes sense…

    Humbly asking for an exact same type of article on my man Grant Hill please!!! Fila –> Adidas –> Nike… Would love to see that list and start a true GHill collection across all 3 brands…

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