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Jordan Chicago Collaborators’ Collection
The Jordan Chicago Collaborators’ Collection uses the eight colors of the Chicago transit line to inspire city-specific takes on footwear and apparel. Nike
2020 NBA All-Star Game

How Michael Jordan and Chicago inspired these All-Star artists

Jordan Brand teamed up with eight collaborators deeply connected to the city

CHICAGO — On a Sunday afternoon in early January, a 95th Street-bound train crept into Washington Station, the only abandoned stop along the Red Line of the city’s L transit system.

The typically empty underground platform, where trains roll through every few minutes without stopping, had been transformed into an expansive production set, densely populated by photographers, videographers, stylists and makeup artists. All eyes were focused upon a collection of creatives, and in this moment, one in particular: Virgil Abloh.

Clad in black sunglasses and a hooded sweatshirt, the fashion designer leaned on the outside of a metal beam, his feet, in a pair of “Metallic” Air Jordan 5s, angled toward the ledge of the track as cameras fluttered around him.

Abloh, 39, is the creator of the fashion label Off-White and the artistic director of menswear for Louis Vuitton. In Chicago, he’s now known as just Virgil, on a similar one-name basis as the African American greats who came before him, Oprah, Obama, Kanye and, of course, Jordan. And with the NBA All-Star Game returning to the Windy City for the first time since 1988, he’s among a team of collaborators who worked with the Jordan Brand to design apparel and footwear employing colors from Chicago’s eight L lines. As the next chapter of the brand’s Unite message, the 21-piece Jordan Chicago Collaborators’ Collection is headlined by Abloh and his Off-White x Air Jordan 5, which will be, without question, the most sought-after shoe during All-Star Weekend.

“For me, it was about, ‘What can I add to this story that’s big already?’ ” Abloh said. “I’m one piece in a very large narrative.”

Before leaving the station that afternoon, Abloh made a point to introduce himself to all of his fellow creatives: a multimedia artist, a barber, a music video director, an up-and-coming female designer, a retired NBA veteran, a sneakerhead-turned-store-owner and a collective of students, from a middle schooler to college-bound seniors.

Just like Abloh, each collaborator has a special connection to Chicago and Jordan — stories they illustrated through the collection.

Yellow Line

SucceZZ (Bobby Simmons and LaVelle “V-Dot” Sykes)

“Somebody walked in and said, ‘You’re gonna do a collab with Michael Jordan.’ … Straight up, I said, ‘Holy s—.’ It was like a gift from God, in all honesty.”

That’s how LaVelle “V-Dot” Sykes reacted to the news that he and his business partner and friend Bobby Simmons, a Chicago native who played in the NBA from 2001-2012, would be collaborating with the Jordan Brand.

In 2008, Simmons and Sykes co-founded a sneaker and streetwear boutique called SucceZZ, which they own and operate together. More than a decade later, the Jordan Brand tapped them to create a hoodie and long-sleeved T-shirt inspired by the L train’s Yellow Line.

“Growing up in Chicago, when you caught the train up north, you’d see graffiti all on the walls, going through the tunnels,” Sykes said. “That’s what yellow train is, graffiti. You saw artwork. You saw tagging. So our collab brings in street culture. We wanna talk to the streets. We wanna talk about what really made us.”

The two met when Simmons hooped at DePaul University and Sykes worked in the city’s most heralded sneaker store, Tony’s Sports. With only one train stop separating them, Sykes sold countless sneakers to Simmons during his college days before he entered the 2001 NBA draft, when he was selected by the Washington Wizards and none other than Michael Jordan, a front-office executive for the team who also decided to come out of retirement and played two seasons alongside Simmons.

“I wanted to make sure that I could get as much knowledge as I could from him,” Simmons said of his time with Jordan. “You just have to look at it from the perspective of a kid growing up in Altgeld Gardens who didn’t really have anything, but had success. How can you make that longevity into your lifestyle? That was my whole vision.”

Sprawled in graffiti across the front of SucceZZ’s Jordan Brand T-shirt is the phrase, “NO PLACE LIKE HOME,” while the back reads, “LIKE CHICAGO.”

“Mike, he’s always brought hope to Chicago,” Sykes said. “It’s bigger than just sneakers. People don’t get that. He’s an image. He’s a brand. To see a black person running a business like this with longevity, it gives hope to everybody that’s around them, that’s connected with him.”

Orange Line

Cody Hudson

Cody Hudson, a multimedia artist who founded a design studio called Struggle Inc., has collaborated with Nike on both apparel and illustration. But this collaboration hit closer to home. Born and raised in Kenosha, Wisconsin, Hudson made frequent trips to Chicago while growing up until he established a creative base in the city, where he’s now resided for more than two decades.

“Living in Chicago in the heyday of Jordan winning all the time, the memories are amazing,” Hudson said. “You’d walk outside and the whole city was going nuts. … Whether you were a huge basketball fan or not, you were just swept up into the positive moment of everyone being out on the streets, hugging and having a good time. It was such a positive and creative energy that was kind of hard to pass up.”

While designing his hoodie and T-shirt, Hudson channeled the euphoric nostalgia he remembers from the Bulls’ Jordan-led run to six championships in the ’90s.

“Based off this Unite idea, I brought this big text in on the back that says, ‘All One.’ I wanted to do this really positive garment. The last couple years, things have been so up and down, from politics to everything else. There’s a lot of negativity out there. My focus was definitely trying to project more of a positive vibe and not get so caught up on the negative. … It just seemed like the perfect opportunity to try to bring people together.”

In 2008, Hudson created a campaign poster in support of Sen. Barack Obama’s presidential campaign. Now, his art is featured on products produced by the brand of another local hero.

“Jordan is so ingrained in Chicago that when I think about Chicago, I think about Jordan,” Hudson said. “You can’t really escape him here, which I feel like is pretty amazing. So, when I was asked to do this, I was kinda blown away.”

Brown Line

Drew the Barber

“The All-Star Game hasn’t been here since 1988, bro, ” said Drew Henderson, aka Drew the Barber, a native of Country Club Hills in the south suburbs. “I really wanted to pay homage to that time. The nostalgia of that time.”

So on the apparel he designed for the collection, Henderson incorporated graphics of old tokens, which the CTA [Chicago Transit Authority] introduced in 1950 and distributed for nearly 50 years before they were replaced with fare cards in the late ’90s, right before the end of Jordan’s reign with the Bulls.

Henderson’s T-shirt and hoodie also feature his personal mantra, and the name of his barbershop, No Cuts, No Glory, through which he’s become the personal barber for some of Chicago’s biggest athletes, from Derrick Rose to Jimmy Butler and Khalil Mack. Henderson started cutting hair in the seventh grade after picking up the trade from his mother, who groomed him and all his siblings to save money. He actually might’ve picked up his first pair of clippers before his first pair of Jordans.

“I’m one of 8, so mom and pops was not getting Mikes in any way, shape or form,” said Henderson, who collaborated with Nike to release his own Air Force 1 in November 2019. “My auntie was the one who looked out. She took me and my sister to go get some shoes. She wound up buying us the Mikes. I literally wore them to bed and pulled my sheets up to see them. Next day, I took ’em off before I went to the bus stop, put them back on when I got in school. It was a sense of pride, a sense of confidence that came along with it. I understand how well he did it, because his shoes still have that feeling.”

Henderson is unashamedly awaiting his opportunity to give His Airness a haircut.

“I know a guy in Chicago who cut Jordan back in the day,” Henderson said. “He told me Jordan came into the barbershop, and people were in awe. But he was a human being, just like everybody else. He talked s—, just like everybody else.”

Purple Line

Sheila Rashad

Nobody forgets his or her first pair of Jordans. Sheila Rashid, a Chicago native with a passion for streetwear, known on Instagram as @sheilathedesigner, definitely hasn’t.

“In high school, fashion and style became important, especially where I went to high school. It was known to be a bougie school,” Rashid said. “Everyone was wearing Air Jordan 1s. Jordans were superimportant. I remember when my stepdad bought me my first pair. It was a huge deal. I always wanted a pair of Jordans but never had one. It was the Jordan 9. A gray and white colorway.”

While designing her own special edition Air Jordan 1 Mid for the collection, Rashid thought back to that first pair and used the brand’s iconic “Cool Grey” colorway — but with a twist. The front half of the shoe is dyed a rich purple, as a nod to the train line Rashid was assigned to creatively channel on her pieces.

“I wanted to do something different,” said Rashid, who appeared in Jordan’s The Ones campaign in 2019, surrounding a women’s slip-on Air Jordan 1 low. “A shoe like you’ve never seen before.”

As for the imagery printed on Rashid’s T-shirt and hoodie, it’s worth noting that she photographed them all herself.

“I feel like this is destiny,” Rashid said. “I’m from Chicago. I’m a designer. I started in streetwear in high school, and now it’s come full circle.”

Pink Line

Lyrical Lemonade (Cole Bennett and Jake “JB” Brode)


“I think we were on Jordan’s radar. They probably asked around and heard good things and realized that we were a good candidate to represent their brand well,” said Cole Bennett, the music video director for Lyrical Lemonade, a multimedia company that he runs with business partner Jake “JB” Brode.

In the past year alone, Lyrical Lemonade, which boasts 2.8 million followers on Instagram, 608,000 followers on Twitter and 12.2 million subscribers on its YouTube channel, has delivered visuals for musical artists from Lil Tecca to Trippie Redd, YBN Cordae, YG and Juice WRLD. And when Bennett and Brode, two Midwest kids who call Chicago home, aren’t dropping music videos, they’re pushing out merchandise, featuring Lyrical Lemonade’s distinct pale blue and yellow straw-in-carton logo.

From a visual standpoint, the pink line couldn’t have been a better fit for Bennett and Brode, natives of Plano, Illinois, and Kalamazoo, Michigan, respectively, who designed their own version of Jordan’s futuristic Aerospace 720 model.

“It started out with the shoes,” Brode said. “They sent a silhouette over and Cole and I just talked about our favorite past Jordan shoes and the elements from them that we maybe wanted to incorporate.” Their vision extended to the apparel, which pairs Lyrical Lemonade’s carton logo with Jordan’s timeless Jumpman.

“It’s one of the craziest feelings,” Bennett said. “I don’t think there’s words that really capture how it really feels. To see a brand that you created come together with something so nostalgic to you … it’s just unreal.”

Green Line

Wings (German Carvajal, Arial Greer, Muhammad Holmes, James Jackson)

When it comes to German Carvajal’s “Aqua” 8s, or pairs of 11s and 12s, he cleans them relentlessly. When the shoes get too worn, he’ll paint over the cracks. And sometimes he’ll draw designs on the soles. But he never thought he’d create a shoe.

Through the Jordan Brand’s Wings program, Carvajal teamed up with three fellow high school students from Chicago’s South Side to design a T-shirt, hoodie and pair of Air Jordan 10s for All-Star Weekend. Since 2015, the Wings program has introduced kids from underserved communities across the country to the ins and outs of apparel and sneaker design while also providing select students with full scholarships to college.

“When I was selected to participate on collabing for a shoe, I was surprised,” said James Jackson, a 2019 Wings scholarship recipient. “I was like, ‘Are we just drawing a shoe?’ They were like, ‘It’s an actual shoe.’ ”

Muhammad Holmes, who’s been learning about design through the Wings program for four years, recognizes the significance of the moment.

“Where I’m from everybody is playing basketball, football … nobody wants to be a designer for Jordan,” Holmes said. “It’s a good opportunity to show kids, even those coming up behind us, that it’s possible to do things like this.”

Both pieces of the students’ green line-themed apparel pay homage to the past by featuring the image of Jordan from his 1989 “Wings” poster. With the Air Jordan 10 as their canvas, Carvajal, Greer, Holmes and Jackson featured all eight colors of the transit system.

“It’s surreal,” Carvajal said. “Back when I was cleaning up my shoes, making my little designs … I never thought I would have an opportunity to create and put my own ideas also on a shoe.”

This is the fifth time the Jordan Brand has released a Wings sneaker, following an Air Jordan 12 in 2016, Air Jordan 1 in 2017, Air Jordan 5 in 2018 and Air Jordan 4 in 2019.

“It’s a blessing. Because most people my color, and our generation, don’t get this opportunity,” Greer said. “Because people overlook us and don’t expect us to be creative. It’s not just about gun violence here. There are actually some youth that wanna do something with their life.”

Blue Line

SocialWorks (K’Shon Newman, Jeremiah Shade, Brianna Townsel, Tremyah Underwood)

At 12 years old, Tremyah Underwood is the youngest collaborator in Jordan Brand history. She joined K’Shon Newman, Jeremiah Shade and Brianna Townsel in representing SocialWorks, which was co-founded in 2016 by Chicago native Chance The Rapper with a vision to “empower youth through arts, education and civic engagement,” according to the nonprofit. Assigned to the Blue Line, the four students made their mark on the collection by using a compass motif that they incorporated into the design of all three of their pieces. On the SocialWorks hoodie and T-shirt, the compass “wears off with time, symbolizing the wisdom gained from a lifetime spent in the city,” reads a description of the apparel on Nike’s website, “and showing that, if you’ve walked these streets before, you no longer need a map.”

The compass is also featured on the soles of a pair of teal, orange and white Air Jordan 1 Hi KOs that Underwood, Newman, Shade and Townsel worked on together.

“On the bottom of the shoes, you can see all the neighborhoods of Chicago,” Newman said. “You can see and actually say, ‘I’m from here. This is my origin. With these shoes, I’m repping where I’m from, Chicago-style.’ We can all relate to being able to see where we’re from, wherever we are. Where we step, we step with pride — Chicago pride.”

And stitched on the heel of each right shoe is the first letter of each collaborator’s first name.

“I know this is something that a lot of people wish that they could do,” Underwood said. “Jordans, they made history … for us to have our mark on a big shoe, it’s crazy.”

Red Line

Off-White (Virgil Abloh)

Abloh’s work with the Jordan Brand began in 2017 with the “Chicago” Off-White x Air Jordan 1 he designed as part of his collection known as “The Ten.” In 2018, he delivered two more pairs of Off-White x Air Jordan 1s in “White” and “UNC” colorways.

But for a collection celebrating the return of the All-Star Game to the city he represents, Abloh wanted to take it back to the beginning.

“This was more like, ‘OK, I wanna do the first shoe that I owned,’ ” said Abloh of the “Metallic” Air Jordan 5s, which debuted 30 years ago in February 1990, when he was 10. At January’s shoot for the Chicago Collaborators’ Collection, he wore a retro pair of the shoe because his Off-White version had yet to be finalized.

“The Jordan 5 … this is the very first shoe that I convinced my parents to buy,” Abloh said. “This was the very first Jordan that I bought out of Foot Locker brand-new. … This is the shoe that I slept with. Bought it, put it at the end of my bed so I could wake up and look at it at eye-level.”

Nostalgia also played a role in Abloh’s design process for his red, black and gray Off-White x Air Jordan woven jacket, pants, T-shirt, boiler suit and the hoodie he donned in the shoot for the campaign.

“The logo on the back is from the jacket I had that my mom got me from T.J. Maxx or something like that,” Abloh said. “The collection is rooted in the first time I saw the Flight logo, that topography, the script, how it looked it was moving through the air.

“It’s from the era,” he said, “that made me believe.”

Aaron Dodson is a sports and culture writer at Andscape. He primarily writes on sneakers/apparel and hosts the platform’s Sneaker Box video series. During Michael Jordan’s two seasons playing for the Washington Wizards in the early 2000s, the “Flint” Air Jordan 9s sparked his passion for kicks.