By Anton Karve

Much like how difficult it is to imagine a NBA star more universally-known than Michael Jordan, it’s hard to imagine a Nike silhouette more iconic than the Air Jordan 1. Designed by Peter Moore and released in 1985 alongside the start of Michael Jordan’s rookie NBA season, the silhouette became inexplicably tied to the meteoric rise of one of basketball’s enduring legends.

Since then, through the efforts of Nike and Jordan brand, the Air Jordan collection has expanded into an empire, with 37 (and counting) silhouettes in numerous colorways making record sales worldwide. However, even within the existing grail status of most OG Air Jordans, there remains one specific colorway that stands above all—the Air Jordan 1 High “Chicago”.

The iconic red, white and black colorway saw Michael Jordan through his introduction to the NBA and kickstarted an entire era for sneakers around the globe. It’s not unreasonable to say that without this specific model, the current sneaker industry as we know it wouldn’t exist.

This begs the question, what was so special about the “Chicago” that led to its meteoric rise to grail status, propelling Jordan Brand into a multi-billion dollar business? To answer this, we need to return to where it all began: Michael Jordan’s Rookie Season.

Rookie Season

The year was 1984, and MJ was deep into his first NBA season as shooting guard for the Chicago Bulls. On his feet were never-before-seen Nike sneakers, draped in colors perfectly matched to his Bulls jersey.

Much work had gone into getting the Air Jordan 1 High “Chicago” onto the court – with only a vague design concept provided by Jordan himself, Nike’s designers had worked tirelessly to create a shoe that fit MJ’s requirements of “different”, “exciting” and “low to the ground”. Deciding to distinguish the shoes using color, Nike made the leap of producing one of the first-ever triple-colored basketball shoes, something that was unheard of at the time.

Even after the design was finalized, Jordan needed to be convinced to wear the sneakers, as he famously called the black and red color palette “the devil’s colors” (in reference to the colors of his college’s rival team, NC State). He also complained that he would “look like a clown” wearing AJ1s. Not even Peter Moore, designer of the AJ1 and then-Creative Director of Nike, could predict just how wrong Jordan was about his criticisms.

Back to the rookie season – with Jordan finally convinced to wear the AJ1 High “Chicago”, he went on to become a NBA fan-favorite, averaging a whopping 28.2 points per game, becoming the second-ever rookie to average above 20 points per game. He was perfectly on-track to his destiny as a global sensation, and just as the world couldn’t get enough of Michael Jordan, sneakerheads couldn’t get enough of the Air Jordan 1s.

The AJ1 Highs released in April 1985 to unprecedented sneaker hype. Demand was so enormous that an entirely new market was created – the sneaker resale market, that eventually grew into today’s multi-billion dollar giant. In NYC’s bus stations, the majority of posters put up to advertise the release were stolen. Everybody wanted a piece of the new AJ1 “Chicago”, and when initial stocks ran out, retailers requested for more – and so Nike sent them much, much more.

Market Saturation

Contrary to expectations, Nike had in fact overestimated the demand and saturated the market with now-unwanted Jordans. The wave of hype had died, and the surplus Air Jordan 1 Highs sat on store shelves for years, experiencing one price drop after another.

This resulted in a huge number of readily available, extremely cheap and durable sneakers stocked in stores around the US. All they needed was for a community to come around and pick them up. The community in question? Skateboarders.

The skate community was an entirely unintended market for the AJ1 High, but in hindsight it makes perfect sense – the Chicago boasted a combination of stability, support, cushioning and durability packaged in a loud yet iconic design – it was everything that a skateboarder could want in a shoe. As former pro skater Jimmy Gorecki said, “before sneaker collecting even became a thing, the Air Jordan 1 was always the shoe.”

The gradual, unassuming spread of Air Jordan 1’s excess stock led to another consequence – anywhere you looked, you’d see the sneaker there, glaring at you in its bright “Chicago” colours. And even as MJ and Nike moved onto newer iterations in the Air Jordan lineup, the AJ1 seemed to refuse to disappear.

In Moore’s words, “I am somewhat surprised by the staying power of the Jordan 1. It seems every new generation of kids has to try it, almost as if they discovered it.” And so, the Air Jordan 1 High “Chicago” solidified its spot in sneaker legends as the beginning – of mass sneaker hype, of widespread resale, of colorful basketball shoes – of virtually all the sneaker phenomena we see today.

An Enduring Legacy

There was no way for Peter Moore (pictured above) and his team at Nike to know just how long the AJ1’s legacy would endure, but endure it did. Even nearly 4 decades after MJ first wore the AJ1 “Chicago” onto the court, anybody who is at least a casual sneaker enthusiast would recognize the silhouette and colorway.

Contributing heavily to this, of course, is Netflix’s Last Dance documentary which reached uninitiated viewers worldwide and brought renewed hype to this icon of sneaker culture. Marketplaces saw a dramatic, nearly $700 spike in resale prices of the “Chicago” following the documentary’s release, and a pair of game-worn, autographed AJ1 “Chicago” was auctioned off for a massive $560k.

What this tells us is that the colorway is here to stay. With every new landmark event occurring in the world that exists between basketball and sneaker culture, both communities will always look back towards the Air Jordan 1 High “Chicago” as the benchmark.

Retro and Reimagined

Of course, with such a stubbornly consistent demand for the sneaker, Nike was always bound to find ways to revive the colorway.

Since 1985’s initial release of the AJ1 “Chicago”, there have been a handful of retros in High, Mid and Low variations, but pictured above are only the Highs. From left to right: Nike Jordan 1 Retro “Chicago” (2015), Nike x Off-White™ Air Jordan 1 Retro High “Chicago” (2017), Nike Jordan 1 Retro “AJKO Chicago” (2021), Nike Jordan 1 Retro High “Trophy Room Chicago” (2021), and last but not least, this year’s upcoming Nike Air Jordan 1 High OG “Lost & Found”, previously known as the “Chicago Reimagined”.

The newest retro colorway references the surplus AJ1s from the overproduced “Chicago” release. Countless pairs of these AJ1s were “lost” as deadstock in store inventories for years before being “found” by the general public once again. This “Lost & Found” theme can be seen across the entire design – featuring cracked leather on the heel typically seen on ancient legacy Jordans, and coming packaged in a weathered shoebox with mom-and-pop-shop-style wrapping paper.

For the November 2022 release of the Air Jordan 1 High OG “Lost & Found”, Nike not only pays homage to the original sneaker, but also acknowledges the entire history of the “Chicago”, both the good and the bad – and that history is precisely what makes the Air Jordan 1 “Chicago” so special.

Images via Complex, High Snobiety & Modern Notoriety