When I first moved to Chicago, I lived in my truck for three months and made money to eat by playing my trumpet on the street.

I had graduated college, moved back home with my mother, discovered the dark and pathetic humiliation of being a college graduate living with his mother, loaded up my blue and silver 1984 Bronco II with most of my belongings and headed north of Kansas. The son of my mother’s friend let me crash on his floor for a week when I arrived but the idea of a homeless guy living with he and his girlfriend for any extended period of time was out of the question, so I crawled back into the Bronco and lived there. For three months. I washed up in the bathrooms of White Hen Pantries and 7-Elevens. When I had gas, I’d drive around the city, discovering my new digs. While I waited for the beauracracy of the Chicago Public School system to process my teaching certification, I was a homeless nomad using the only skill I had to gather enough cash to eat. I played my horn.

It was the closest I’ve ever been to actual poverty — scrambling by day to make enough cash to buy a meal and some gas for my “home” and parking in non-residential zones everywhere and anywhere so I could sleep in the back of the truck. I didn’t have a Busker’s license — the city’s way of controlling the flow of desperate musicians looking for a few bucks to eat, of course — so I was occasionally busted by the authorities. Once, a policeman took all the money out of my trumpet case and pocketed it. When I complained, he threatened to haul me in, so I just went someplace else, made a sign that said “The Police Took All My Money Today” and played the blues. I cleaned up that afternoon.

A routine was essential. I figured out that the best times of day to play were in the mornings near various El stops, mid-day in the Loop, afternoons were most profitable near the Lincoln Park Zoo. The high time for busking was end of the day, after everyone was headed home from work. Inside the actual El stops (on Grand or Chicago) were prime real estate and other players had pretty much staked them out but somewhere near Randolph and Wabash was always a solid spot. I made more money when I didn’t wear a hat. I made more money when I wore a dress shirt. The more clean cut I presented myself as, the less like a homeless person I was and the change became bills simply because of how I was dressed.

As I calculated my meager earnings, I realized I was bringing around $8.00 a day — tax free! It was enough most days to get at least one solid meal a day and some basics — toothpaste, deodorant, razors, and gas — the survival kit of urban life.

The experience, while brief, stuck with me. I felt the slight helplessness of being untethered from the rest of society, of being looked at as somehow not a part of the rest of us, of knowing that if I were injured in some way, I was fucked. Sure, my mother cared that I existed but not one single person in the entire sprawling metropolis gave two shits whether I lived or died. I was far more afraid of the police than the other homeless or various criminals I encountered. The uneasy sleep of someone almost completely exposed all the time. The loneliness. The near despair.

Three years, a job and an apartment later, when my fledgeling theater company decided to do an evening of odd experimental pieces, I brought it all to bear.

We were doing the show in Puszch Studios, a dance studio located where the Strawdog Theater is now, on Broadway across the street from the Hotel Chateau. The piece, called “Frogs” was a solo jazz performance, written while I took acid and listened to a CD of tree frog sounds on repeat. Before the show, I would dress in full indigent gear — dirty chinos, a black t-shirt with a button down shirt missing a few buttons and a tear up the side. Torn gym shoes and an old duster coat. A ball cap that was grease stained. I would stand about half a block from the theater entrance a half an hour before it started and play.

Straight, No Chaser.

Perfidio.

The Blues Walk.

As I’d play, people would walk by and decide to either just not look at me as they rushed by, walk by but sneer in disgust and maybe mutter something nasty under their breath, or stop and throw some change in my case. Given that the location I chose was across the street from a hotel filled with people society has given up on, being gripped for change was pretty common in the area. Most passers-by had created that bubble of blindness that occurs to those of us who have when faced with so many who have not. As if by looking up and away or down at the sidewalk, those who are at the end of their rope cannot be seen, cannot infect us with whatever illness they have. It is a bubble that, while completely understandable, is no less ugly for the justification.

The audience would pass me by and enter the space. The house music played. And about five minutes after the start time, I would pack my trumpet up and walk up into the venue as if I were just looking for a bathroom or a place to sleep. I’d lumber into the cabaret space among the audience. I’d ask a few for a handout. The entire room would get very tense. Most shows no one said anything and just hoped that someone from the theater would bounce me. Once, a young white guy with a date looked at me and said “Hey. Hey! You don’t belong here! This is a show. You need to leave!”

I ignored him. I ignored all of his type. I ignored the stares, the uncomfortable coughs, the slightly abrupt whispers. Once I had heightened the discomfort in the room, the technician would change the house music to the Tree Frog CD. And I would hear it. And open my trumpet case and play the piece I had written while tripping. I’d finish, pack up my horn and walk away and go change for the rest of the show.

We did the show for 12 weeks — 24 shows. Every Friday and Saturday night I’d play the part, play the trumpet on the street. 24 times, people would pass me by in disdain. A young white couple on a date, happily walking hand in hand, suddenly shifting gears, getting quiet and somber as they both looked in other directions than right at me as they quickened by. A group of guys who just shoved past, almost knocking me down in the process as if to dare me to speak up. A kid — maybe six or seven — stopping with his parents to listen and his father giving him a dollar to put in my case in spite of the fact that his father knew it was a waste of a dollar and that, by the time the kid was sixteen, he wouldn’t remember the moment. It was exactly like when I first moved to the city — I felt apart from the rest of the tribe, floating among people but not of them. This time, though, it was as an artist, observing behavior and assessing the cost of each interaction with an almost anthropological interest.

On night 23, things were proceeding as before. Then a shambling black man with a dirty paper bag dodged traffic to get to me. He was coming from the Chateau. He wore a faded “Taste of Chicago” t-shirt and a doo-rag. He couldn’t have been older than 40 but they were a hard 40 years.

“Excush me.” He was talking through his clenched jaws and a bit of spittle flew out of his mouth from the force of his effort to speak. I kept playing — I was “in character” — but I acknowledged him with a look into his eyes.

“Excush me. I live up there…” and he pointed to a fourth or fifth floor window. “…and I had my jaw broken becaush of a bad night. My jaw ish wired shut. Shee?”

I nodded and continued to softly play a riff on Miles Davis’ “All Blues.”

The Hotel Chateau was what used to be called a flophouse. It had weeklong room rates. It had hourly room rates. Prostitutes, alcoholics, drug addicts and the last bit of the world’s refuse ended up there. It as four steps and hop from sleeping under Lower Wacker Drive. It was the most sorrow-filled building I had ever seen. The name — “Hotel Chateau” was like a meanspirited joke on all who resided within.

“Shee? I can’t eat sholid foodsh. I been depreshed becaush of it but every weekend, you come here. And play. I lishen every week. Itsh a good thing. Caush my jaw ish wired shut. I don’t have no money but I have thish cheesh.”

And he handed me the bag. I stopped playing. I took the bag and looked inside and there it was — a brick of government issue yellow cheese, still shrink wrapped. I didn’t know what to say but started to politely refuse.

“No, you take it. I got nothing elsh and you give me a gift with your mushic sho I’m want you to have thish. I can’t eat it anyway — my jaw ish broke.” And he laughed and waited.

“Thank you.” I said. “What do you want hear?”

He looked surprised. “Shomething Chrishhmash?”

It was May. Christmas was forever over or forever forthcoming. I thought for a second and pulled my horn to my lips. I played a blues infected version of “White Christmas” and he smiled through his clamped mouth and clapped his hands like a child. I finished the song with a flourish and he grinned a strained and painful smile. I bowed slightly. He applauded. Then he turned and shuffled back across the street, across the Boulevard of Broken Dreams, and back into the Hotel Chateau.

I closed my case and went upstairs into the theater but I didn’t play the piece I had written while high as a kite in the comfort of my one-bedroom apartment in Edgewater. I played something different. I played something improvised. It was based on the chords of “White Christmas” and, like all truly improvised music, that song was played once and never again. No one noticed that it was different. But it made me sad and angry and hopeless.

So many people with so much walking by and ignoring need and this one man, a man that O. Henry would deem one of the Magi, giving the only thing he had as a show of gratitude to a stranger. This man, whom no one would remember and no one would see his act of kindness, returning to Oblivion as if he belonged there.

The following night — the last night of our performance on Broadway — was the last time I ever played my trumpet on the street.