My train from Chicago to New York City was rescheduled a day later due to mudslides, so I ended up having two days of busking in Chicago. I checked a bag for 24 hours in the Chicago Union Station, and booked a hotel online. I wrangled a slightly early check in and then headed out towards Millennium Park to busk. As I approached the park, I could hear other buskers. A good sign!

I set up in the middle of the block across from the Chicago Art Institute and began playing. Tons of tourists, art students, and sports fans passed by each way, and since traffic was so high, I repeated many of my most upbeat songs again and again. I earned three tips.

Then I caught the attention of a belligerent, unkempt wino. He swayed towards me with a fat bottle of wine and a joint clenched in his lips and I instinctively snatched my iPad (the most expensive piece of gear I have with me) and stashed it in my bag. He leaned over my music stand. I avoided his yellowed gaze and continued playing a montuno, thinking something about how music soothes the savage beast. “Keep playing,” he commanded. He gyrated near me, then spiraled off and began harassing people. People who were smaller than him, mostly women and small men. He would block their progress, entangle himself with them, try to anger them — successfully.

I knelt down and put my self-defense item in my right-hand pocket, in case I had to make him have a very bad day. The next time he came near me and leaned up to my face, I said, “Squirrel!!” and pointed to my left. He looked that way. “Look, look at that guy!” I said, pointing. He ambled off in the direction of the imaginary squirrel/guy.

He attempted to square up to a large Mexican man who seemed to be somewhat protectively (I hoped?) standing near me. The man stared him down till he slunk away to annoy more tourists. I thought about packing up, but felt like it put me in an even more vulnerable position, on the ground putting my gear away. I wasn’t afraid of him, really, but I did have a primal fear of liquid touching my gear.

He came back to me. Not missing a beat with my hands playing the piano, I looked him dead in the eyes and said almost apologetically, “Hey man, I’m just trying to make money here.” It seemed to work and he went away. This scenario repeated one more time, minutes later, and again I appealed to the decent human buried somewhere inside: “C’mon man, let me make some money OK?” This time he went away for good.

The handsome security guard from the building where I was busking came out and complimented me on my voice, but told me the (commercial) tenants were complaining and I needed to move. “I wonder if I was repeating songs too much,” I asked. “That could have something to do with it,” he said.

I packed up and as I rolled my way home, a few blocks away I saw the same guy harassing a different busker. Only in this case, it was a much tighter corner and a large man kept running interference between him and the busker, as he darted in again and again like a moth drawn to a flame. 

Speeding away with my heavy load just in case he noticed me, I was so proud of myself for handling this guy. This is a classic busker conundrum, and here I’d gotten through it with flying colors. Now, I live in the San Francisco Bay Area so handling crazy people is a skill developed from early childhood. Not to mention the fact that just being a performer exposes you to bad behavior like this — even in the best clubs and most elite towns. Having said that, in no way do I wish to experience this kind of thing often or again.

The next day, I went for a run along the River Walk and talked to a police officer who said he’d seen me running when he was passing by on his police boat. I noticed he had a dive team shirt on so we talked about that. Then I mentioned the wino situation and asked if performing on the River Walk would be better, since I figured this guy is likely still bothering people around Millennium Park. “Oh yeah, they don’t let any of those people down there — they make too much money to put it at risk,” he said. “You’ll be fine.”

Sure enough, I set up down there and it was so beautiful. I probably would have gotten more tips if I had been more assertive about asking for them, but there was a sign that said no peddling and I didn’t want to get kicked out. (I should also set up a primed tip jar.) So I settled for two tips and a delicious free Chicago-style hotdog from a nearby restaurant that asked me to perform for them the next day. I told them I’d be leaving for New York, but I do want to come back!

Next up: I Lost My Credit Card (But It’s OK)