Remember when we had a president that cared about sneakers? Obviously they were not as important as his political leanings, but important, nonetheless, to folks like me. Though the occasion was rare, seeing Barack Obama in a pair of cool sneakers engaged an area of my mind that I don’t think I expected a politician to ever touch. It didn’t seem forced.

It wasn’t an effort by a politician to make it seem like he fit in with the cool crowd. Obama’s appreciation for sneakers seemed to be an authentic part of his nature. While some might assume it was him alone, some of the ease with which he was able to break these invisible barriers was due to the people around him. He had a team of like-minded individuals that were masters in their respective fields surrounding him.

One of those people was Chris Holliday. A hard man to find and one of the most low-key people I have ever had the pleasure of speaking with, Holliday is a man of many connections. In fact, it was Holliday that helped Complex secure then-Vice President-elect Kamala Harris for an appearance on Sneaker Shopping. When it came to Obama and sneakers, Holliday was the go-between. He says he sourced a lot of sneakers for the former president. However, he is more than just a sneaker guy.

Chris Holliday and President Barack Obama
Chris Holliday with President Barack Obama. Image via Holliday on Instagram

Looking through Holliday’s social media accounts—well, account—the first thing you notice is that he has some very influential friends. From the professional world of basketball to the White House, Holliday keeps company with those at the top of their game. The second thing you notice is that his sneaker collection runs pretty thick. And unlike most sneakerheads, he’ll rock a fresh pair while dressed in the usual political uniform of a suit and tie. It’s a bit jarring and refreshing, but also speaks to the role he plays in connecting the dots between Black men and the political process that so often adversely affects them. 

Let’s be honest, when we think of politics, a Black man in a suit in a fresh pair of Jordans isn’t the image that comes to mind. For Holliday, the sneakers are just a part of who he is. And as he navigates the world of politics, he is slowly changing the expectation and perception of a larger community that is now starting to understand their power. 

“As you grow up and you see different types of people from where you’re from,” he says, “you realize who are the authentic people and who are not the authentic people.”

Holliday was most recently the adviser to surrogate outreach for the Biden campaign. While the title sounds vague, the position helped the Biden campaign listen and connect to Black men. As Holliday describes it, his role was to “curate the culture to translate and become a bridge for African-American men.” With 2020 disrupted by the COVID pandemic, the job of connecting anyone to anyone was hard enough, let alone to a very specific group of people. Banking on his experience in marketing and promotions at iHeartRadio, Holliday developed a sense of how important the role of media can be in shaping the conversation. He also knows how individual voices can be more important than any media conglomerate.

“One thing I realized is with athletes and entertainers, especially athletes right now, they are their own media companies,” Holliday says. “You wake up in the morning, you scroll to your feed. Me and my nephews, my cousins, my friends, we don’t get up in the morning and turn on CNN, ABC, or NBC.”

One of those athletes is Chris Paul, who Holliday stood next to on the campaign trail in one of the few photos I could find of him.

“Chris is an essential piece in connecting politics, sports, and culture, which gave us a chance to ask our own questions and tell our own stories to President Joe Biden and Vice President Kamala Harris,” the NBA veteran says of Holliday. “What makes it even cooler is the fact he looks like us, speaks our language, and dresses the way we dress—Js and all.”

While Holliday didn’t know it at the time, his start at iHeartRadio and front row view of the process of turning artists into stars would be the prep work needed to take on his role as a surrogate during the Obama administration. Starting out as a deputy press secretary in Florida for the 2008 campaign, Holliday began learning the ins and outs of the world of politics and how he could step in and help. During that initial campaign, he started to realize the power of telling stories and being true to yourself.

“You just woke up in the morning, you tried to give something, give all that you have, but also trying to interject your own piece of who you really are. Obama, the campaign, was all about telling your story,” he says.

That authenticity and storytelling often came through the eyes of Holliday’s athlete friends. Back in the Obama administration, Steph Curry became a vocal advocate of the president, speaking against gun violence and appearing as part of the Malaria Initiative. Curry and Obama also came together on sneakers when Under Armour created the super-limited Under Armour Curry 3 sneaker that honored Obama’s back-to-back terms as president. Holliday was the connector.

“We all trust Chris,” Curry says. “He always tells it straight with a real feel for how we can make the biggest difference while still staying true to who we are, like we did together for the Democratic National Convention. And he’s got that special personality that bridges and connects with people of every background while staying true to who he is, which is really rare. It’s just dope to see a brother like Chris moving in these circles, representing the culture, and just trying to do right for people.”

The Barack Obama version of the Under Armour Curry 3 celebrating the president's back-to-back terms
The presidential version of Stephen Curry's Under Armour Curry 3 sneakers. Image via Curry on Twitter

With the Biden administration leaning heavily on the world of social media, Holliday was able to connect the campaign with culture in a way that the Obama administration didn’t need to. How athletes use their voice has changed tremendously since 2008. From podcasts, to YouTube vlogs, to full-on media and production companies, athletes and celebrities alike are telling their own stories, their own way. And with the NBA relaxing rules on footwear, we’ve seen a ton of messages in support of all types of causes across the sneakers we see on court. For Holliday, that voice and perspective is important. He believes that everyone needs to see people that look like people they know.

While there is an audience for the larger networks to reach, Holliday believes that there is a far greater impact when seeing someone from your own neighborhood, where the most help is needed, interacting with and championing the causes that are important to those communities. 

When asked about his role in past administrations and how he got there, Holliday is quick to keep it as authentic as you can get.

“For me, as a young Black man, I didn’t grow up saying, ‘Hey, I want to go work at the White House,’” Holliday explains while laughing under his breath. “I didn’t grow up doing that.” 

Through his experience working in politics, Holliday started his own company, Swing State Strategies. In addition to advising political campaigns and presidents on being inclusive, he is also tapped by CEOs and other executives to advise on how their companies can be more diverse. As an adviser, Chris is often sharing what seems all too obvious to most of us.

Chris Holliday Sneaker Shopping
Holliday on the set of Sneaker Shopping. Image via Complex Original/Mark Hanson

“I tell people: How you can be inclusive of Black people is hire Black people,” he says. “Put them in these rooms.”

In addition to advising politicians and CEOs, part of Holliday’s job is to educate. For many, the world of politics and big business seem daunting and out of reach. He looks at it a different way. As he helps change the narrative around Black men, he also uses his platform to let people know that Harvard, Yale, and Princeton aren’t the only roads that lead to success. He believes that intelligence goes beyond what you score on an exam and extends to how you are able to feel a room and respond accordingly so that everyone leaves happy.

“The smartest executives ain’t the guy that got on the shoes and tie,” Holliday says.

Holliday believes the smartest executives that come to him for counsel extend a hand to the younger executives that look, speak, and think differently than they themselves do. He also feels that the more inclusive your surroundings, the more inclusive the result. It’s this style of thinking that has led to a more inclusive sneaker world for us all. Big brands like Adidas are partnering with designers like Jerry Lorenzo to run entire divisions; Foot Locker named Melody Ehsani to run its women’s business. It is these companies that wind up succeeding, according to Chris.

Holliday has witnessed these ideas in practice from within his own family. His cousin Victor, a video game designer and executive at Universal, wears Jordans to work. He notes that this distinction separates Victor from the majority of executives in a way that makes the rooms he is in more diverse. Holliday doesn’t believe that the neighborhood you come from, or how you dress, disqualifies you from being an executive. 

As part of his job, Holliday fields calls from executives asking about the latest footwear—a sign he believes comes from a genuine place of interest to understand sneaker culture. It is this new clashing of cool and smart that is bringing a different voice to the world, and CEOs are starting to recognize the value it has in creating a more diverse and inclusive business. Evidence of this can be seen in the release of the Air Jordan 11 “Jubilee” that brought in over $175 million over the holiday season. Holliday became the resource for many of the executives he works with when it came to securing their pairs.

Air Jordan 11 Jubilee CT8012 011 Profile
The Air Jordan 11 'Jubilee.' Image via Jordan Brand

“You have to create dialogue, context, and open communication to figure out how to make everybody feel inclusive in this environment,” Holliday says. To him, this is important because if it isn’t done, those same people will continue to make laws and policies that don’t pertain to the larger audience. Not just for African-American men, but also their kids. 

The unresolved issues that exist in BIPOC communities aren’t always a priority in the world of politics, and, yet, in the past 12 months we’ve again realized how important the conversation can be to making us all feel like we have a part in the direction of this country. For Holliday, this connection is more important than ever. From CEOs of venture capital firms and tech companies, to some of the best basketball players in the world, to presidents, senators, and city councilmen, Holliday is bringing together people in a way that politics hasn’t been able to do for as long as we can remember, all while teaching and being authentic to himself and his community. 

Introduced to me as Obama’s sneaker guy, it is clear that Holliday’s role is much larger and more impactful than that. He serves as a bridge. He speaks and connects the world to young Black men and lets them know they don’t have to fit in a box to change the world, they can just be themselves, fresh Js and all.