Air Jordan 1 Retro High OG 'Chicago'

The shoe in the Bulls' colors

In October 1984, Nike signed Michael Jordan, then a rookie with the Chicago Bulls, to a six-year deal worth $2.5 million, three times larger than any NBA shoe contract of the time. The signature shoe that came out of it was the Air Jordan 1, designed by Peter Moore. It went on public sale on April 1, 1985, at $65, a high price for a basketball shoe then.

Moore drew the shoe's Wings logo, a basketball with wings, which sits on the ankle collar. The Jumpman logo did not exist yet; it first appeared on the Air Jordan III in 1988.

Of the original 1985 colorways, the white, red and black pair in the Bulls' team colors became the one most associated with Jordan. Today it is simply the 'Chicago,' and resellers describe it as the most famous colorway of the Air Jordan 1.

Jordan's first season

Jordan played all 82 games in 1984-85, averaging 28.2 points, 6.5 rebounds, 5.9 assists and 2.4 steals. He was named Rookie of the Year, made the All-Star team and was a second-team All-NBA pick. He also wore Air Jordan 1s in the 1985 Slam Dunk Contest.

A broken foot limited him to 18 games the next season. In Air Jordan 1s he also scored 63 points in a playoff game, a performance that led Larry Bird to compare him to a divine figure.

The first run of 50,000 pairs sold out, and the shoe went on to generate more than $150 million in sales. Jordan Brand was formally introduced as its own label in 1997.

Getting the Chicago right

The Air Jordan 1 was first reissued in 1994, and returned in 2001 and again in 2013. The 2013 retros brought back Nike Air branding on the Air Jordan 1 High, but one sneaker writer complained that Jordan Brand 'dropped the ball' on the Chicago, leaving out details from the original.

The 2015 pair was the correction. It released on Saturday, May 30, 2015, for $160, timed to the shoe's 30th anniversary. It carried the red Nike Air label on the tongue and Nike Air on the insole, had no Jumpman on the heel, and came out of the box unlaced like the 1985 pair, with spare red and white laces.

Nike pulled the shoe from its online store at launch and released it months later through a raffle that began September 30, 2015. On October 3, 2026, a new pair was listed at a sneaker resale shop at $661, about four times the original retail price.

How to identify the 2015 pair

Look for style code 555088-101 on the box label and the size tag. The official colorway is White/Black-Varsity Red: white leather panels as a base, Varsity Red overlays, and black Swooshes and collar.

The tongue carries a red 'Nike Air' label rather than a Jumpman, the insole is printed with Nike Air, and the heel is clean of Jumpman branding. The Wings logo is stamped on the ankle collar.

Several later Chicago releases share the colorway but not the code, including the aged 2022 'Lost and Found' pair (DZ5485-612). The 555088 prefix marks the mid-2010s Retro High OG run.

Why it matters

The 1985 originals are four decades old, so the 2015 pair became the faithful Chicago that collectors could buy and wear, and the reference later Chicago retros are compared against.

The 30th-anniversary pair opened a run of 555088-code Retro High OG releases in original 1985 colorways, including the 'Bred' in 2016 and the 'Royal' in 2017.

The numbers

Style code

555088-101

Colorway

White/Black-Varsity Red

Release date

May 30, 2015; Nike online raffle from September 30, 2015

Retail price

$160

Production

Not published by Nike in any source found

Original 1985 retail

$65

Timeline

1. Oct 1984

   Michael Jordan signs a six-year, $2.5 million deal with Nike.

2. Apr 1, 1985

   The Air Jordan 1, designed by Peter Moore, goes on sale at $65.

3. 1985

   Jordan is named Rookie of the Year after averaging 28.2 points.

4. 1988

   The Jumpman logo debuts on the Air Jordan III.

5. 1994

   The Air Jordan 1 is reissued for the first time.

6. 1997

   Jordan Brand is formally introduced.

7. 2001

   Another Air Jordan 1 retro run.

8. 2013

   Nike Air-branded Air Jordan 1 Highs return, including a Chicago that critics found lacking.

9. May 30, 2015

   The Air Jordan 1 Retro High OG 'Chicago' 555088-101 releases at $160 for the shoe's 30th anniversary.

10. Sep 30, 2015

    Nike opens an online raffle for the pair after pulling it from its web store at launch.

11. Oct 3, 2026

    A new pair is listed at $661 at the same shop.

The world in 2015

• Apr 12, 2015

  Hillary Clinton announces her 2016 presidential campaign.

• May 2, 2015

  American Pharoah wins the Kentucky Derby, and Floyd Mayweather Jr. beats Manny Pacquiao.

• May 20, 2015

  David Letterman's final Late Show airs.

• Jun 2, 2015

  FIFA president Sepp Blatter announces his resignation amid a corruption investigation.

• Jul 14, 2015

  NASA's New Horizons makes the first flyby of Pluto.

• Jul 20, 2015

  Cuba and the United States restore diplomatic relations after 54 years.

• Jul 29, 2015

  Microsoft releases Windows 10.

Price record

This is an asking price, not a sale. It is what a seller wanted on the date shown. Asking prices often sit above what buyers pay, but an ask is not a ceiling: a sale can land on either side of it. It is not a value.

By reference price, Air Jordan 1 Retro High OG 'Chicago' is number 59 of 100 in the sneakers entries of the FLOAT 100. 22 of those 100 rest on a realized sale; the rest carry an asking price or a guide value, and each page says which. Rank within the FLOAT 100 itself (63 here) is editorial: how much an object defines its field, not price alone.

Did you know

• Peter Moore drew the Wings logo; the Jumpman did not appear on a Jordan shoe until 1988.
• The 2015 pair came unlaced in the box, just like the 1985 originals.
• Nike pulled the shoe from its online store at launch and sold it months later by raffle.
• Jordan's $2.5 million Nike deal was three times larger than any NBA shoe deal at the time.
• Jordan scored 63 points in a playoff game wearing Air Jordan 1s, and Larry Bird compared him to a divine figure.