About Boardroom

Boardroom is a media network that covers the business of sports, entertainment. From the ways that athletes, executives, musicians and creators are moving the business world forward to new technologies, emerging leagues, and industry trends, Boardroom brings you all the news and insights you need to know...

At the forefront of industry change, Boardroom is committed to unique perspectives on and access to the news, trending topics and key players you need to know.

All Rights Reserved. 2022.

The “Cool Grey” Air Jordan 11: An Oral History

The inside story on how cross-category inspiration, online forums, and basketball’s best young talent made old Air Jordans matter to a new generation

Perhaps more than any other symbol, sneakers represent the convergence of sports, fashion, and business.

Almost annually, the Air Jordan 11 releases in various colorways — some old, some new — to international pandemonium and record-setting sales. The Michael Jordan signature debuted on-court in the GOAT’s first comeback to basketball, offering a new narrative and new look to the most important endorsement in sportswear history.

In 2000, just five years after their arrival and 20 months after Mike’s retirement, the Jordan 11 returned to retail in retro form. Initial re-releases paid homage to pairs worn by Michael in the past, but a March 3, 2001 launch looked to risk it all by doing something new: dressing the hoops holy grail in a lifestyle palette.

And to celebrate the “Cool Grey” Air Jordan 11’s latest revival on Dec. 11, we spoke to the creatives, collectors, and cultural icons associated with the trailblazing 2001 launch. They touched on the ideation, pandemonium, and nostalgia surrounding this industry-shifting shoe, setting the stage for its newest chapter.

Sign up for our newsletter

Get on our list for weekly sports business, industry trends, interviews, and more.

“This Air Max 95 thing is hot. What if we just did a grey version of the shoe?”

The Air Jordan 11 debuted at retail in 1995, releasing in three mid-top styles over the course of the Chicago Bulls‘ historic 72-10 season.

At the same time, a running shoe was changing the shape, shade, and sentiment of sneaker culture.

Nike Air Max running shoe (James Keyser/Getty Images)

Gentry Humphrey (former VP of Jordan Brand):  I’m usually up at 4 a.m. I woke up and said, ‘This Air Max 95 thing is hot. What if we just did a grey version of the shoe?’ I went right to the office and drew it with a marker.

As soon as the developers came in, we started working on it and put all the materials together. We wanted to tell a luxe story so we went with nubuck instead of textile. 

Mike thought it was good, but he wasn’t doing backflips like when he saw the Concords.

“The first thing I remember is the leaked sketch.”

Internet reaction was stronger than Jordan’s.

Only in its infancy, Web 1.0 was blossoming at the turn of the millennium as special interest pages and forums highlighted hobbies and created communities. In 2000, two sneaker sites mattered more than any other: NikeTalk and Instyleshoes.

Steve Mulholland (Instyleshoes & Sole Collector founder): I sold a business to the guy who created voicemail and I was sitting on stock options. I was heavy into kicks, so I created Instyleshoes. NikeTalk and ISS were blowing up when the “Cool Grey” 11 leaked because there was no other shoe like that up to that time.

Todd Krevanchi (NikeTalk co-founder): The first thing I remember is the leaked sketch. Oftentimes, the leaked sketch was the first thing that came out. It would’ve been from a trade book that a Nike rep would’ve had and got leaked.

Gentry Humphrey: Shades of grey. That’s what we called it when we started to sell it to the sales team. We were known for using cool grey as the primary color so that’s how it became known as the Cool Grey.

SteveMulholland: The 11s are the holy grail of Jordans and they rarely ever stepped outside of the lines on colorways. To have a color different from the OGs? It was a big freaking deal.

Gentry Humphrey: There was a potential to create some hysteria if we did it the right way, because I really didn’t know if it was going to pop off.

“If we rock these, we might have a chance to be in a SLAM Up!”

As Web 1.0 survived Y2K and sneakerheads salivated over the sketch, when would the world actually see these “Cool Grey” 11s on foot and in 3D form?

Gentry Humphrey: We weren’t 100% sure where Michael Jordan was going to be so we started to seed pairs early to some of the guys.

Quentin Richardson (Clipper Legend/Jordan Brand athlete): I damn sure remember when we got the Cool Greys: before everybody.

Travonne “Blk Tray” Edwards (Compton hooper): Tyson Chandler would show up with a new pair of shoes every practice at Dominguez High. He was getting stuff so early. The first time I saw the Cool Grey 11s, I thought they were an exclusive for him because Mike had never worn them. 

Patrick Christopher (Cal Legend/The Black Ralph): I remember Josh Childress coming on Mayfair [High School’s] campus and he had them. It’s tough to describe the feeling of something like that in a time without social media, being a sneakerhead. To have them that early? It was like a first wear every time because of the reactions he got.

Quentin Richardson: People don’t even know it’s coming because there’s no social media telling you about the Jordan Brand lineup for the fall. A lot of times they just saw it on us. People knew who we were at this point so they knew it was legit. They’d lose their shit and ask to take pictures with us and we’d just bask in the glory.

Gentry Humphrey: A lot of that had to do with wear-testing. We had guys in the research lab at campus testing them, but there’s nothing like having someone who’s playing D1 or pro put a whole different stress on the shoe. We had to get them out there because we weren’t 100% sure if or when MJ was going to come back.

Travonne Edwards: They actually got a chance to debut them before Mike.

Gentry Humphrey: We would do focus groups with Cincinnati and I don’t know if Kenyon Martin was the first guy with them, but on that team he was the face. To me, not a bad guy to be one of the first.

Quentin Richardson: I can vividly remember wearing them immediately. Me and D-Miles knew that Mike Bibby was going to wear them first. So after the first few times of that happening, we had to wear them so SLAM could take pictures of us and say we were the first to wear them.

Quentin Richardson as a member of the LA Clippers (Todd Warshaw /Allsport)

Travonne Edwards: Darius Miles and Quentin Richardson doubled down on the visibility. They were touchable. Even though they were celebrities, they were going to Westchester and Dominguez games. You could see them! It was believable because they were not that much older than us, but they’ve got cool cars, cool gestures, and cool shoes. And those things meant the world. 

Quentin Richardson: At this point, I’m 20 years old and D-Miles is 19. We’re kids! So any time we get any shipment in, we’re going straight to Fox Hills Mall and going up in Foot Locker.

Patrick Christopher: Looking at D-Miles and Q, you became a Clipper fan just to see what kicks they were wearing or which lob they were gonna throw that night.

Quentin Richardson: When you get the Elite Package from Jordan Brand, those weren’t shoes they sent you to play in. So I immediately called and ordered two to three more backup pairs for the crib.

Gentry Humphrey: I always felt like the best shoes are the ones that work on and off the court. So we made it feel like it was an elevated version that people would want to wear when they’re trying to stunt or go out. That was the primary call: the first foray into what a true lifestyle shoe for the Air Jordan 11 could be.

“I flew to Europe for Cool Grey 11s.”

After months of looking at the leaked sketch and seeing them on the feet of Jordan Brand’s best, the “Cool Grey” Air Jordan 11 was set to release — but not on the day collectors were accustomed to.

Travonne Edwards: It was the first Saturday retro. Before, we were leaving school to go get Jordans on Wednesdays. You could just hitch a ride during lunch and come back real quick. 

Gentry Humphrey: That was definitely strategic. We had to do the right thing. You don’t always know that things are hot, but we knew that the Cool Grey 11 was going to be a big one. We had to do the responsible thing and move the date so kids wouldn’t skip school for it.

Matt Tomamichel (Corporate Got ’em Owner) : In Cincy, everybody knew that the Cool Greys were coming — everybody. With the other Air Jordan 11s, you could pre-order them off Eastbay if you called at 11:50 p.m. and held for 10 minutes. There weren’t many Cool Grey 11s, so you had to go hunt.

Todd Krevanchi: The Cool Grey 11 was the first shoe I ever paid above box price for. My buddy was the manager at Champs and he said, ‘Listen, I can get you a pair but it’s gonna cost you a couple bucks.’ It was only $20 above retail, but it was like, ‘Holy shit, I’m paying more?’ It was totally bizarre at the moment.

Jameer Nelson as a member of the St. Joseph’s Hawks (Al Bello/Allsport)

Matt Tomamichel: I had a friend who worked at Champs. When we pulled up we see at least 500 people standing outside the main entrance. You see everyone pressed up to the glass of each store. People are running up the escalators, there was no organization – nothing. You could see a baby getting pressed up to the glass.

Jameer Nelson (NBA All-Star, NCAA Freshman of the Year): I definitely had a shoe guy. I wasn’t waking up early to get in line. [Laughs

Brian Romney (Collector/@OGSneakerNerd): The line got intense in Orange County. There was excitement and a buzz about it. Luckily, I had no issues getting them. But not far from us? Chaos, apparently.

Travonne Edwards: It was crazy. It wasn’t violent, but if you were in sneaker culture and that was your main thing, you were going to do what you needed to do to get them. As a basketball player who fell in love with shoes when I was nine years old, I had to have them.

SteveMulholland: I flew over to Europe for the Cool Grey 11s and hit every Foot Locker from Italy to Amsterdam. I think I bought 450 pairs. We sold them on Instyleshoes and any profits I put right into starting Sole Collector.

Quentin Richardson: It was a thing at that point. That was part of why me and Darius became a popular duo. It was pandemonium when we went to the mall. Once people knew they were official, I would have my friends in the league relying on me as the plug.

“Michael Jordan is the ultimate endorsement.”

As Jordan Brand prepared for an era without Mike, it rolled out a fashion-friendly retro ready to be worn with all the latest lifestyle gear.

Months later, the GOAT validated what the youth loved.

Gentry Humphrey: On the Cool Grey 11, we intentionally went away from the lime green on the Air Max 95 because I wanted to make sure it had an opportunity to hook up with multiple things. 

G Fiume/Getty Images

Matt Tomamichel: That Monday, I wore them to school with a Sean John hoodie and matching sweats. I was fresh. You could see everybody looking saying, ‘Bro you could’ve helped me!’ Man, nobody could’ve helped anybody on this one.

Jameer Nelson: I always tried to rock as much heat as I could in college. That shoe? I got them and wore them right away.

Travonne Edwards: I did it all in that shoe. They were my Swiss Army knife. ENYCE was popular at that time, I had a Mark Ecko sweater, and I was wearing Iceberg History then. White tees were huge at that time, too. All you had to do was switch out the jeans.

Quentin Richardson: It confirmed that we were right because everybody else felt how we felt. 

Travonne Edwards: Michael Jordan wearing them was even more validation that they were official. He validated them because Michael Jordan is the ultimate endorsement. 

Gentry Humphrey: Whenever you have the great validator put them on? At 40 years old, he was giving people 50 and 51. He was still able to keep people on the edge of their seats. To have him validate the colorway? It’s huge.

“That shoe sparked a movement”

Before 2001, the buzz around old shoes was building, but the energy around new colorways was not.

After the Cool Grey 11, it was a whole new game.

Todd Krevanchi: The first Air Jordan retros were in 1994 and that experiment was considered to be a failure. But the Cool Grey Air Jordan 11? Nike figured it out: we have this great library here, let’s just throw new covers on these books.

Gentry Humphrey: The Cool Grey 11 was meant to be that one extra color. We had some all-white versions, some all-black solid versions, all-black with black midsoles and clear outsoles, and we had all-white that had no color pops to them at all. Grey basketball shoes really weren’t popping back then, we were taking a chance.

Jonathan Daniel /Allsport

SteveMulholland: That shoe sparked a movement in the industry. Nobody knew how it was gonna hit. The Laney 5s? That was an authentic look into his high school career but it didn’t have the same cool. With the Cool Grey 11, they reached to the far side. It didn’t have a real story to it, but when we saw it we knew.

Gentry Humphrey: It was like when the Air Jordan 1 first came out: a Chicago colorway, people freaked out because nobody in the industry was doing it. So the same way that had an impact on the industry, the Cool Grey did. It was so different that it flew in the face of what everybody was expecting.

SteveMulholland: Gentry is a hell of a guy. That dude got a lot of hate from hardcore guys that didn’t want colors that weren’t game-worn, but Gentry pushed the envelope. There are so many career-making or breaking decisions that Gentry had to make on his own and he killed it. He absolutely killed it.

Quentin Richardson: This was breaking the mold. That Cool Grey 11 stood out and went harder than anything I’d ever seen.

Patrick Christopher: They take me back to the golden era of being a sneaker collector. It felt pure.

Travonne Edwards: I had a buddy who took them off at a pickup game. He sat them on the side and is looking as he’s playing. He went up and down the court two more times and my neighbor stole them. That’s how hot that shoe was at that time.

Steve Mullholand: There was so much energy around it. People were losing their freaking minds. To me, it said that Nike is listening to the public. Those guys at Jordan Brand had their finger on the pulse to do something different.

Gentry Humphrey: In my opinion, there will be nothing like the first one. It may be hotter in 2021 because of the success that goes with that shoe. You’ve got generations that have grown to fall in love with that shoe. The fever today is probably hotter because of sheer numbers, but when it comes to excitement? I don’t know. The first time you do something, it’s hard to top that.

Sign up for our newsletter

Get on our list for weekly sports business, industry trends, interviews, and more.