‘Skate or Die’: A young Chicagoan counts on his skateboard to get him to a better life

Tough but uplifting documentary details the struggles of surviving in gang territory.

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Leo Castillo leads a drive to build a skatepark in his Little Village neighborhood in “Skate or Die.”

Flyback Productions

The first time we see 17-year-old Chicagoan Leo Castillo, he’s in the hospital, receiving treatment for an injury of some sort, and he’s asked the question: Tell me what happened. Tell me a story.

Cut to a montage of Leo and his friends skateboarding in and around the Little Village neighborhood — sometimes as seen from a camera mounted beneath a skateboard. Cruising past a graffiti-spangled wall and a shop with gowns in the window, down tree-lined streets, near a birria restaurant, in the parking lot of a bank, as Leo tells us, “Skateboarding came into my life through my older brother. He had bought me a skateboard for my … seventh birthday. And he was basically trying to put me on the RIGHT path, by telling me that gangs are bad. Because [everyone in my family was] in gangs.”

What follows is an extraordinary piece of street-level filmmaking and storytelling from Chicago director Ryan Ferguson that hits home and tells a tough, sometimes heartbreaking but also uplifting story with a raw power that few fictional works can match. Inspired by a 2007 Chicago Tribune story by Azam Ahmed (who now works for the New York Times and serves as the film’s writer-producer), “Skate or Die” is culled from more than 100 hours of footage shot by Ferguson in the late 2000s and early 2010s, and with a great assist from editor Zebediah Smith, the end result is an 84-minute, journalistically impressive documentary that knows how to get out of its own way and let the story and the subject matter come to three-dimensional life in a stylistically appropriate fast-paced fashion.

‘Skate or Die’


A documentary directed by Ryan Ferguson. No MPAA rating. Running time: 84 minutes. Screens at 4:15 p.m. Saturday at the Music Box Theatre. (Panel discussion follows.)

From that opening montage, we flash forward a year and we’re back in the hospital with Leo as he explains to a nurse he was shot in the leg — resulting in an injury that could prevent him from ever skating again. “It was like we all took a hit,” says one of Leo’s skateboarding friends.

“I was just in the wrong place at the wrong time,” notes Leo, with a flat resignation in his voice that reminds us random violence is nothing new in the world he knows. Leo talks about living right near the border of Little Village and Pilsen: “The bad aspect of it is there are so many gangs … that once you cross one side, you’re scared ’cause you’re going to get shot on THAT side, and when you try to get back home you’re afraid they’re going to mistake you for somebody else.” If that doesn’t send a chill down your spine …

Director-cinematographer Ryan Ferguson employs the classic fly-on-the-wall approach as he chronicles Leo’s recovery and takes us inside Leo’s home, with his harried mother trying to hold things together in rough living conditions. Yet for all its sobering aspects, “Skate or Die” also provides inspiration and hope, as we see Leo spearheading the effort to build a skatepark in the neighborhood. This is the stuff of a Hollywood movie. The struggle is mighty, the obstacles are many, but we’re rooting for this young man and hoping he can ride his love of skateboarding to a better, more purposeful life.

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