Cassius Life Featured Video
The Smithsonian Institution Holds Press Preview For New National Museum Of African American History And Culture

Source: Chip Somodevilla / Getty

Vice President Kamala Harris frequently made the headlines during her 2020 campaign as she was often photographed in her Converse Chuck Taylor Sneakers. Like one of the occupants of 1600 Pennsylvania Avenue before her, a certain Barack Obama, Harris liked to wear sneakers as a reflection of her down-to-earth nature and authenticity. However, Obama and Harris have more in common than politics or an appreciation for comfy kicks; they are both connected to one particular guy who helps them, and many other high-powered individuals, get their hands on some of the freshest footwear out there: Chris Holliday.

Holliday spoke with Complex about how a marketing and promotions career at iHeartRadio led to working with heads of state, C-suite execs, and some pretty big names in entertainment and sports. “For me, as a young Black man, I didn’t grow up saying, ‘Hey, I want to go work at the White House,’” he said. “I didn’t grow up doing that.” Holliday calls himself “The Advisor and Consigliere” on his Instagram page, and a quick perusal shows photos of him hanging out with the likes of the Obamas, the Bidens, and 3x NBA champ Steph Curry.

Holliday’s segue from entertainment to the world of politics came when he was a member of Barack Obama’s presidential campaign in 2008. The sneakerhead says his experience as a Florida deputy press secretary showed him the magic to winning people over: it was to be honest and transparent about 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,” he told Complex. “Obama, the campaign, was all about telling your story,” he says.

When Obama won his second term, Golden State Warriors guard Steph Curry became a very prominent backer of the president. Sneaker company Under Armour put out a one-off, highly limited run of the Under Armour Curry 3 sneaker to celebrate the back-to-back success of the first Black president of the United States – and Holliday was the plug.

“We all trust Chris,” Curry said. “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… 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.”

Holliday has since translated his knowledge and list of contacts into creating his own company, Swing State Strategies. Although he continues to advise politicians and corporate bigwigs on how to rock sneakers at some of the most unconventional occasions, his ultimate goal is to create more opportunities for minorities and break with the convention that the best people for the job always have to look a certain way, too.

“As you grow up and you see different types of people from where you’re from, you realize who are the authentic people and who are not the authentic people,” he said. “I tell people: How you can be inclusive of Black people is hire Black people. Put them in these rooms… The smartest executives ain’t the guy that got on the shoes and tie.”