Aaron Herrington represents a long and illustrious lineage in our culture. Escaping small-town U.S.A. to chase big-city dreams is a time-honored tradition in skateboarding. Like so many before him, Herrington gravitated to San Francisco at the tail end of the aughts to immerse himself in the downtown scene during the height of the HUF D.B.C. era.

Fresh out of high school, the Corvallis, Oregon native found himself living in weekly hotels in the Tenderloin, and working odd jobs to get by while honing his craft on the streets synonymous with names like Carroll, Hufnagel, and Busenitz. This period laid the groundwork for everything that would come after.

A couple of years later during a trip to New York, Brian DeLaTorre convinced Herrington that a pre-GX1000 San Francisco was dead, and N.Y. was where things were happening. It’s hard to leave the city, period. Even harder when someone is convincing you to stay. He made a pivotal decision at Tompkins that afternoon, which would alter his career trajectory permanently.

Once planted in N.Y., Herrington was scouted by Josh Stewart. This landed him the opening part in Static IV, and an introduction to Pontus Alv. He would ultimately turn pro for Polar in 2014, a couple of months before the video dropped. Static and Polar cemented Herrington’s status as an underground king. They were also the start of his ongoing collaboration with Theories of Atlantis, which has endured and evolved over the past decade.

When the streets are watching, going mainstream is inevitable. Herrington was introduced by Converse not long after turning pro; colorways and international tours ensued. The kid from Corvallis had officially arrived as one of the world’s premier professional skaters. Unfortunately, there was a dark side that came with that. Herrington has publicly addressed issues with alcoholism and mental health that he battled during those years, which resulted in him going sober at the end of 2017.

Soon after, he unveiled Chrystie NYC—his clothing imprint with Pep Kim. The brand has dropped two videos, and developed a formidable team over the past couple of years. And the design aesthetic speaks for itself. With his leg cast from an injury this past August freshly removed, Aaron dropped by the studio for a two-hour conversation with Lee that covers all of this and more during Episode 20 of Mission Statement.