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Luxurious Legacy: An Ode to the Air Jordan 2 ‘Chicago’

Devin Robertson

In 1985, Nike and Michael Jordan changed the world of basketball and sneakers forever when they debuted the Air Jordan 1.

The reasonably priced shoe came in over 20 colors during its initial run and has consistently been one of the most celebrated sneakers in the history of Nike. When it came time to produce the Air Jordan 2, Air Force One designer Bruce Kilgore and the late great Peter Moore of Air Jordan 1 and Nike Dunk fame had a monumental task on their hands. The Air Jordan 1 was a revolution for its time, so it would be simple to create a paint-by-numbers affair for the sequel, right? Well, that’s not what His Airness and the team chose. 

The Air Jordan 2 was a complete overhaul from the initial offering, though there is a prototype version of the sneaker that skews more closely to the original. Kilgore and Moore toyed with several vital portions of the Air Jordan 2 before putting it all together, with MJ famously wearing the Air Jordan 1.5, an Air Jordan 1 with the sole of the Air Jordan 2 attached after returning from a broken foot, during the 1985-1986 season.  During its on-court tenure, the young Chicago Bulls star regularly wore the high and low variations of the sneaker. 

Image via Jordan Brand

The air unit and polyurethane sole are among a few of the myriad of upgrades the Air Jordan 2 received in relation to its predecessor. Jordan and Nike set out to make the sneaker the epitome of luxury and added a heel counter for stability. The dash of faux iguana skin found on the quarter panel set the stage for the use of another iconic animal print in future Jordan models. Jordan and the Swoosh took it to the next level, and to ensure the luxurious qualities they sought; the Air Jordan 2 was crafted in Italy with soft, high-quality leather. Upon its release in 1987, the sneaker was limited to 30 stores in 19 cities at its release giving it an enigmatic and unobtainable air.   

Michael Jordan in the Air Jordan 2 ‘Chicago’ (via Getty Images)

While these upgrades created a shoe that exuded elegance, it came at a cost. The sneaker spiked by $35 in price, going from $65 to $100. The AJ2 dissuaded some due to a couple of factors. Perhaps wary of the deluge of fines from David Stern, the Air Jordan 2 was the first in the Air Jordan line not to feature a black colorway in its original release. In fact, the Air Jordan 2 launched with the fewest colors of an Air Jordan to date, with two minimal colorways released: a white and red “Chicago Home” colorway and a white, red, and black “Chicago” colorway at the beginning of the season and low iterations of the same colorways in the second half. Jordan had something to prove that year, winning his first career scoring title, averaging a career-best 37.1 points, and becoming the first player since Wilt Chamberlain to score 3,000 points in a season.  He also became the first person to record 200 steals and 100 blocks in the same season, along with First Team All-NBA and NBA All-Star nods. 

The Air Jordan 2 “Chicago” may be the most famous of the underrated silhouette due to the way it made its presence loudly known at the 1987 All-Star Weekend, where MJ won the first of his two Slam Dunk Contest trophies. While the loud introduction is what brought eyes to the sneaker, the quiet details are the true game-changer of the shoe. The Air Jordan 2 opted to forego the Nike Swoosh for smaller Nike branding on the heel counter. The Air Jordan 2 was a radical experiment, and the designers left Nike almost immediately after its completion. Kilgore and Moore tried to coax Jordan into leaving, which he considered partly due to public reaction to the Air Jordan 2. This led to Tinker Hatfield joining the Jordan Brand team for the following iteration, where he drew inspiration from the prior history of the line, including the Jordan 2, to form what would be Jordan’s biggest undertaking to that point – the Air Jordan 3. 

After its time in the sun, the Air Jordan 2 faded away until Nike dipped their toe in the water of retroing sneakers during Jordan’s first retirement from basketball. Starting in 95, Jordan Brand re-released the Air Jordan 1-3 in a move that was too forward-thinking for the time. Due to the rumored destruction of the original Jordan 2 molds, the Air Jordan 2 was nearly lost to time. It was rumored to be reverse-engineered for its first retro in 95 by vivisecting a pair of the original sneaker.  Though the concept of retros eventually caught on and became a major part of the Jordan Brand operation, the Jordan 2 remained relatively quiet throughout the years.

Carmelo Anthony in the Air Jordan 2 “Melo” (via Getty Images)

Further spurring the lost mold rumors, the shrouded Air Jordan Retro Nu 2, which looks similar to Russell Westbrook’s initial Why Not.01, arrived in 2003. It appeared the mold business was finally over when the sneaker finally saw some love when Denver Nuggets phenom Carmelo Anthony donned the sneaker in a team-appropriate colorway in 2004. Though that sighting stirred the hopes of some AJ2 diehards, the sneaker still appeared sparingly until 2010 when the “Away” colorway, now known as the upcoming “Chicago” colorway, first returned with the white and red “Chicago Home,” following in 2014. 

The silhouette continued to appear here and there over the years, with 2008’s Eminem “The Way I Am” and 2018’s “Black History Month” colorways being highlights in the shoe’s history. The Air Jordan 2 also held the distinction of being the first Air Jordan featured in the Doernbecher Freestyle collection held annually by the Doernbecher hospital since 2007. Patient Sheridan Brenton dressed the sneaker in a black, green, and yellow colorway as a nod to the Oregon Ducks.  2021 is when the intensity for the Air Jordan 2 finally began to rise after years of being underrated. Legendary creative director Virgil Abloh remixed the low version of the “Home” option with the colorway released in November 2021, just days before his tragic passing. 

Virgil’s remix was the harbinger of what was to come in a big renaissance for the groundbreaking sneaker. 2022 was the year of the Air Jordan 2; the silhouette served as the canvas for many collabs throughout the year, including revisions from J. Balvin, Union, Nina Chanel Abney, A Ma Maniere, Titan, Two18, and Shelflife. After a year of celebrating one of MJ’s more under-the-radar sneakers, Nike and Jordan are wrapping up the year with the return of the Air Jordan 2 “Chicago,” in which Jordan displayed some of the most uncanny features in all of basketball, including that spectacular free throw line dunk in 1987.

Michael Jordan in the Air Jordan 2 White/Black (Photo via Getty Images)

Though the Air Jordan 2 may not be the most popular shoe in Michael Jordan’s signature line, it is one of the most important – it proved that the brand was willing to take risks, it showcased Michael Jordan’s overwhelming popularity with its eschewing of the Nike Swoosh, and it highlighted Mike’s habit of debuting sneakers during the All-Star game, a trait he kept most of his career. 

The groundbreaking Air Jordan 2 ‘Chicago’ returns on December 30 via Nike and select retailers.

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