There’s no question that Michael Jordan’s domination over the NBA throughout the 1990s has had a huge impact on his influence in sneakers. After capping off his career with the Chicago Bulls with the an unbelievable buzzer beating jump shot in the 1998 NBA Finals, there wasn’t much else he could’ve done to better solidify himself as a legend in the sport or in sneakers. At that point, Jordan really didn’t have to do anything else NBA related, but by the new millennium he traded in his Bulls jersey for a suit as he became a minority owner and President of Basketball Operations for the Washington Wizards. While Jordan got acclimated into his new roles as a businessman, the early 2000s was an awkward time for Jordan Brand, producing some of its best and worst sneakers. The Air Jordan XVI, however, was released in the midst of it all as Jordan Brand’s most underrated sneaker.

Designed by Wilson Smith, the Air Jordan XVI released in February 2001 as MJ’s second post-retirement sneaker. It was also the first sneaker after the Air Jordan III to not be designed by Tinker Hatfield. Marking the beginning of a new era in Jordan Brand designs, the Air Jordan XVI embodied Jordan’s present-day life as a businessman, while remembering his past as a player. Incorporated in the design were styling cues from previous Air Jordans — patent leather from the XI and icy outsoles from the V. The sneakers also included a pair of leather gaiters. Put them on and the XVI had a sleek look suitable for off the court. Take them off and the XVI was a full-fledged performance basketball sneaker.

Darius Miles
Darius Miles wearing the Air Jordan XVI in 2001. Image via Getty/NBA

The problem was that the sneakers just couldn’t connect to Jordan’s fans. Following the release of the Air Jordan XV, a sneaker regarded as the worst Air Jordan even by Tinker Hatfield, the XVI seemed to be headed down the same path. They released in a Bulls-inspired black and red colorway while MJ sat behind a desk in the offices of the Washington Wizards. Though the XVI hadn’t been worn by Jordan on the court aside from the sneaker ad, it was well represented by Jordan Brand athletes like Ray Allen, Jason Kidd, Eddie Jones, and Michael Finley. There are people who still want the sneaker because Darius Miles made them look so cool. It was also marketed through a long ad with Mos Def and his song, “Umi Says.”

That changed in September 2001, when Jordan decided to come out of retirement for the second time to play for the Washington Wizards. Wearing the “Ginger” Air Jordan XVI during the part of the 2001-2002 season, old man Jordan lead the Wizards to a 37-45 record in a valiant effort. Despite Jordan’s on-court connection to the sneakers and a 18-win improvement from the Wizards’ previous season, his performance never matched up to his days with the Bulls, making the season forgettable to say the least. What little bit of noise Jordan did make in Washington was muffled by a young Kobe Bryant, who was emerging as the league’s next Michael Jordan with a second consecutive Championship win in 2002.

Michael Jordan Wizards 2001
Michael Jordan wearing the Air Jordan XVI in 2001. Image via Getty/NBA

Even as Jordan’s limelight as the NBA’s star player started to fade, diehard fans and collectors had plenty of releases to gravitate towards. The Air Jordan XVI released in other colorways like “Midnight Navy,” “Cherrywood” and two low-top variations, but it was Jordan’s older silhouettes that grabbed the attention of consumers. The early 2000s brought in some of Jordan Brand’s best releases and ultimately kick started the craze for Air Jordan retros. With Air Jordans 1, III, V, VI, and XI retroing in OG and new colorways during the first two years of the new millennium, the Air Jordan XVI was easily overlooked. But think about it: It’s an Air Jordan with a patent leather toe and icy outsole, all the elements people look for in a pair of Js. When the Air Jordan XVI and VII Countdown Pack came out in 2008, it was easily one of the better pairings in that collection, and it made people think more highly of the shoe.

Fifteen years later, the Air Jordan XVI is making a retro comeback of its own. This year, the silhouette has seen two extremely successful (and extremely limited) releases with the Trophy Room x Air Jordan XVI and the SoleFly x Air Jordan XVI. Now, for the first time since 2001, the original “Midnight Navy” colorway is releasing. From the basketball court to the boardroom, the latest Air Jordan XVI  drop features a combination of White and Midnight Navy, that can be worn as a home or an away sneaker. With today’s popularity of retro Air Jordans, the XVI surely won’t be as under appreciated as it once was.