Caught on camera: Chicago street performer robbed mid-song

CHICAGO - In the heart of downtown Chicago, where crowds rush past and street corners double as stages, one performer’s voice has become a familiar soundtrack. 

For the past decade, Andrew David has been singing on some of the city’s busiest streets—turning everyday moments into something memorable.

"I have been singing since I was four years old," David said.

Before bringing his performances to Michigan Avenue and State Street, David honed his craft underground.

"Honestly, before I started street performing, I started subway performing and one thing led to another and I ended up street performing most of the time," he explained.

Performing outdoors year-round, David says he’s experienced just about everything—from harsh weather to unpredictable crowds.

"This isn't necessarily the first time I've been robbed," he said.

But what happened Monday afternoon at Michigan and Madison felt different.

The backstory:

While performing, David says a high school student approached his setup, waited for the right moment, and walked off with his tip box filled with cash from passersby.

"Honestly, I don't know… I want to say like it was a nice day… I at least had $100," David said.

But for David, the loss wasn’t really about the money.

"Right after he picked up the box… I grabbed my microphone and said, ‘Could you at least bring the box back?’" he recalled. "I wasn’t gonna chase down a kid."

Moments later, a bystander returned the box. Still, the incident stuck with him—so he reviewed video from his recording setup, which he uses both for content and safety.

That’s when he noticed something unsettling.

The same teen had been lingering near the box roughly 10 minutes before taking it.

David posted the footage online. Soon after, the student was identified. School officials reached out, and the teen’s mother contacted David directly.

"The principal reached out to me this morning… his mother reached out to me and she was really nice and apologetic," David said. "Hopefully there’s a lesson learned at the end of the day."

The school later reimbursed David for the stolen money.

Despite the experience, David says moments like these haven’t shaken his commitment to performing.

Instead, they’ve reinforced it.

"I’ve never been in a position where I can see the immediate impact," he said of street performing. "This is really just… coming from my heart."

What's next:

David continues to perform regularly, often drawing crowds with covers by artists like Sam Smith.

And even in a city that can be unpredictable, he’s not stepping away from the mic.

Performing in Chicago, he says, can be tough—but it’s worth it.

Because no matter what the city takes… he’s still choosing to give.