The Most Talented Panhandler I’ve Ever Met


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Panhandler Art

Panhandling is a pretty sensitive topic. To give or not to give? Can you trust what they’ll do with your money? How else can you help? These are all important, debatable questions, and I’m sure we’ll discuss them here. But it just ain’t happening today. Instead, I want to share my experience with the most talented panhandler I’ve ever met.

If you’ve ever been to New York City, there’s a 98% chance you’ve been approached by a panhandler. On a tiny island with 1.6+ million people, the panhandling and homeless community in NYC is much more visible than most cities. And when there are that many people asking for the same thing, it means going above and beyond the cardboard sign and cup of change to get your dollar. Especially in the city known for its cold, hustle and bustle, heart.

One winter day, I was on my way home from my office in Midtown to our cozy apartment in the Upper East Side. That meant taking the 6 train from the 51st Street station to 86th Street, a total of four stops. It just so happens to be that that line happens to be the busiest in the country, so personal space gets very, well, personal. I joined the herd of passengers into a train, settled into my spot by a pole, and fixed my gaze ahead.

Out of the corner of my eye, I saw a sweet, elderly Chinese woman smiling. She was happy about something. Or crazy. Which isn’t surprisingly uncommon on crowded trains. I peeked around someone standing in front of me to see what she could possibly be looking at. There was a middle-aged, disheveled African American man with a clipboard and Sharpie pen in hand. I looked at the paper and saw an incredible portrait of that same smiling Chinese woman. He was putting the finishing touches on it and I was absolutely mesmerized. As the train slowed for the 59th Street stop, the woman collected her belongings to stand up. The artist took a second to sign his name and a brief note that I couldn’t see. He handed her the paper, she bowed, and off she went.


This intermission brought to you by the most talented panhandler I’ve never met.

I couldn’t help but smile. Clearly, I wasn’t expecting to witness what I did in a city known for being rough around the edges. Where people would rather bury their heads in newspapers and headphones than dare interact with fellow passengers. Where brashness typically drowns out kindness. This was an awesome moment. Suddenly, I saw the man with clipboard pan the car. Before I knew it, his eyes had already met mine.

Anyone who knows me knows that I hate drawing attention to myself in public. I’d rather fade in the background, go about my business and surround myself around people and places where and with whom I feel comfortable.

And so I quickly fiddled around in my pockets looking for my cellphone that would be of absolutely no use to me hundreds of feet below ground. After staring at my phone for a few seconds, I casually looked up and scanned around. I glanced in his direction and he was working feverishly on his next portrait. Phew. Dodged that bullet. And then he looked up and fixed his gaze on me. CRAP!

As he drew, nearby passengers began watching him work. And naturally, they wanted to see his subject: me. I did my best to be a good sport and enjoy the moment. I watched as a recognizable face appeared on his paper. I smiled at others who were analyzing me against his artwork. And suddenly, before I knew it, I heard my exit cue. The next stop is 86th Street. After spending just two or three minutes drawing me, and sensing my departure, he signed his name and wrote a brief note. He got up and handed me the portrait. I thanked him and looked the drawing over. I noticed the scrawled note at the bottom of the page that read, “Please tip if you like.”

Panhandler portrait

Normally, I feel slighted or duped when confronted for money, especially on the spot. But this dude was talented. Despite bumps, screeching halts and pressed against the clock, he not only drew an awesome portrait, but he entertained half a train car. So I grabbed the largest bill from my wallet ($5), handed it to him, and thanked him again.

And that’s the most talented panhandler I’ve ever met. He was contributing and creating something of value. Despite his circumstances (whatever they might have been), he was still using his God-given talent to do something. He was being the best panhandler he knew how to be.

Have you ever encountered a panhandler that made your day?

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37 Comments

  • Reply Lisa @ Elle Sees March 12, 2013 at 9:42 am

    Loved this! My husband ran into (who I assume is) the same guy a few weeks ago — and we have a very similar picture now hanging on our bulletin board in the kitchen. I’ve always appreciated when people offer something or show a little talent before trying to collect money. And like you said, it’s kind of refreshing to make these small, fleeting connections in such a big city. Amazing that drawing was done in just a couple subway stops!

    • Reply Johnny March 12, 2013 at 7:32 pm

      No way! What a small, awesome world! It really was so nice to have that moment of connection with fellow passengers.

      The $5 was a heckuva lot better than one of those caricature artists in Central Park who prey on tourists and charge $20 for a really lousy drawing.

  • Reply Johnny Moneyseed March 12, 2013 at 9:44 am

    Woulda sucked for him if you didn’t carry cash!

    (The dude in that video that you posted went back to drugs after he was given a chance in the radio industry)

  • Reply Brian March 12, 2013 at 10:05 am

    I don’t get many pan handlers bothering me. I have a very good “leave me the f**k alone” face I can put on in public. It has served me well.

    I also live in a city that th emayor just proposed an ordinance to ban panhandling in the downtown area and near the sporting arenas… it is causing quite the debate.

    • Reply Johnny March 12, 2013 at 7:37 pm

      I learned that face and walk very quickly in New York. It was less the panhandlers that bothered me and more the folks trying to get me to sign up for crap.

      I wouldn’t mind panhandling bans… but I don’t really know if the majority of panhandlers would observe it. There’s no way they’d pay any citations. And I can’t imagine they’d book them in our already-crowded jails. So I wonder how they’d intend to enforce that law.

  • Reply Mary March 12, 2013 at 10:14 am

    Wow this is a touching story :) I’m from Long Island and commuted to the city for college for two years so I’ve definitely come across my share of panhandlers. I think the most memorable was a teenage boy that was selling candy bars. He said something along the lines of “I ain’t here selling candy for no boy scout troop or school fundraising. I’m here selling candy bars so that I can make money and look fly”. What a guy right? haha.

    • Reply Johnny March 12, 2013 at 7:38 pm

      Hahaha. That’s amazing. I’ve always liked honest panhandlers. It doesn’t mean I’ll always give them money, but I appreciate them coming clean with their true intentions.

  • Reply Chris March 12, 2013 at 11:16 am

    I only give money to those guys that say have signs that say, “need money for beer” because we all need a beer now and again. I’m kidding, I never give pan handlers anything. I stopped giving to pan handlers when I saw the special on Stossell about how it’s all a huge scam.

    • Reply Johnny March 12, 2013 at 7:41 pm

      I haven’t seen the Stossell special, but I’ve tried to help enough of them who “needed money for a bus ride home,” only to find them on the same corner a few days later. I’ve actually been to a few metro cities that have signs posted that tell you not to help them because they’re provided help whenever they want at the local food banks and homeless shelters. Interesting experiment in tough love or something.

  • Reply Alan March 12, 2013 at 11:33 am

    I typically give if the person is entertaining or has a gift. Sometimes out of sympathy I will give anyways. But I will have to say the funniest panhandler I have seen in action is the guy in San Francisco down by the piers. He hides behind these branches from a tree or bush while sitting down in the middle of the side walk. He watched as people walk towards him not paying attention and then scares the crap out of them. Sadly enough, people constantly fall for it even though there are bystanders waiting for him to succeed. Once he does people throw him money.

    • Reply Johnny March 12, 2013 at 7:43 pm

      YES! I’ve never been up to San Francisco, but I’ve seen videos and had friends relate their stories of sitting and watching him scare the crap out of people for hours. Now that’s a deserving dude. He actually probably makes more money than I do. :)

  • Reply Roo // NiceGirlNotes March 12, 2013 at 11:44 am

    Weird, I got a little choked up reading this. Not, like, TEARS or anything, but.. my emotions were emotional.

    I would have totally given him $$$. I wonder how he’s doing now.

    • Reply Johnny March 12, 2013 at 7:48 pm

      “Not, like, TEARS or anything, but.. my emotions were emotional.” <— Awesome. I remember calling Joanna as I was walking home from my stop to our apartment and relating the story and I couldn’t stop smiling. It was a really cool experience that touched a lot of different emotions/thoughts. Based on Lisa’s comment up above, it sounds like he’s still at it. Hopefully he’s making good choices with his income.

  • Reply writing2reality March 12, 2013 at 12:15 pm

    Awesome story! I went to college in an urban environment and saw and was approached by countless panhandlers. Unfortunately, because of this I became pretty desensitized to their plight. There are so many times you can offer to buy them food only to have them curse at you for not giving them money. It’s like, “Sorry dude, just reading your sign. ”

    At the end of the day, there are those who are making the best of their position and status in life, and those folks will be rewarded for their efforts.

    • Reply Johnny March 12, 2013 at 7:53 pm

      After just a few months in the city, I was totally tuned out and desensitized, as well. It’s a shame because no humans should be ignored, especially those in need. But when you see them doing nothing to help themselves get out of their terrible situation, it seems futile. And luckily a lot of our taxes and church tithes go to ensure these folks have beds to sleep in and food to eat, so there’s some comfort in that.

  • Reply debtperception March 12, 2013 at 2:17 pm

    I encountered my first panhandler when I was 10, at Disney World for my Make-A-Wish. A young, aspiring artist approached my family and drew me a quick sketch of a cartoon character that kind of resembled a pirate, peg-legged version of Spongebob years before Spongebob even came out…to this day I wonder if his dreams came true. I don’t know how much my dad gave him but that was by far the most inspiring panhandler I’ve met.

    • Reply Johnny March 12, 2013 at 7:56 pm

      That’s amazing! How cool would it be if that guy ended up being the Spongebob creator. What’s so sad about so many panhandlers, especially those with talents or past achievements (like being a Harvard grad), is that so few ever end up becoming reacclimated with society. And often times, substance abuse is to blame. Drugs/alcohol can be terrible things.

  • Reply Grayson @ Debt Roundup March 12, 2013 at 2:18 pm

    That is pretty awesome. He is differentiating himself from others and using what he knows. I would give him $5 as well. I don’t really encounter too many panhandlers and I don’t mind it.

    • Reply Johnny March 12, 2013 at 7:57 pm

      If there were ever a city to stand out among others, NYC is it. And that goes for the panhandlers, too.

  • Reply Mrs. Pop @ Planting Our Pennies March 12, 2013 at 6:28 pm

    He earned every penny of that $5 by entertaining you and providing you with a keepsake that you’ve obviously treasured for a while now.

    • Reply Johnny March 12, 2013 at 7:58 pm

      While it probably won’t be going in a $200 Michael’s frame, I’ll definitely hold onto it in my keepsake organizer. :)

  • Reply Mo' Money Mo' Houses March 12, 2013 at 6:33 pm

    Oh wow. That’s such a cool drawing. I encounter pan handlers every day on my walk to work, but most of them are either rude or just have a sign. I feel bad for them but I honestly never give money.

    • Reply Johnny March 12, 2013 at 8:00 pm

      That particular occasion was one of just a handful that I ever felt moved/compelled to give something. Which means that I rejected at least two or three every single day on my commute to and from work. It’s a tough situation.

  • Reply MindyC March 12, 2013 at 9:40 pm

    I saw my fair share of talented people on the subways, and they are one of the many reasons I love the city.

    My mum always encourages us to give our spare change to the homeless, but I grew up in a city where homelessness is rare. Once I let on that I stop doing so in the Big Apple because of, well you know, the abundance of homeless people. Also I am a student. I was chided because a couple of quarters means a lot more to someone sitting out on the street.

    • Reply Johnny March 13, 2013 at 10:21 pm

      Other than the suffocating cattle car moments, I actually enjoyed the subway. There was rarely a dull day during the commute.

      You have a good mom. When we lived in NYC, we were still in debt and scrimping to get by, but that probably wasn’t still the best excuse to not give. Losing a little change here and there wouldn’t hurt us much. I just hate wondering if I’m enabling their addictions and worsening their problems by giving them money.

  • Reply KC March 12, 2013 at 11:13 pm

    Amazing. It’s nice to hear stories like this once in a while. And it’s even better if you can experience it. And I’ve heard of that homeless man with the golden voice. Last thing I heard was he got a job. I wonder where he is now..

  • Reply Joshua March 13, 2013 at 9:00 am

    I have to admit that I didn’t read who was actually writing the post, but for some reason assumed it was Johanna. When I got to the portion of the post with the picture, my initial response was, “Dude, Johanna looks like a guy!” Then I realized my mistake. :). Great story!

    • Reply Johnny March 13, 2013 at 10:24 pm

      Hahaha. Awesome. Yeah, that’s when Joanna was going through her “I-want-to-cut-my-hair-short-and-grow-facial-hair” stage. :)

  • Reply Amanda March 13, 2013 at 1:29 pm

    I did have my day brightened once by a panhandler on a train in Buenos Aires. He played an acoustic guitar and sang, and I would have given him the change in my pocket if only he wasn’t on the other side of the car. He was pretty awesome.

    • Reply Johnny March 13, 2013 at 10:28 pm

      There were quite a few musical panhandlers. Some weren’t that great and were pushy with requesting money. But some were just awesome. I always loved the mariachi bands. Another time, there was a Chinese man playing Greensleeves on this one or two-stringed fiddle thing. We were coming from Brooklyn, so it did get a little old after 15 minutes or so, but he earned a few bucks from us. :)

  • Reply C March 13, 2013 at 6:24 pm

    I love this! It’s not quite the same, but I do have one little story out of Boston.

    On an exit leading to Cambridge/Boston, there are usually at least two to three pan handlers working their way through slow-moving rush hour traffic trying to get into the city during. Once, a man stood off to the side with a large cardboard sign that read, “I BET YOU CAN’T HIT ME WITH A QUARTER.” That man made SO much money that day. (Nobody that I saw actually aimed for him; you could just hear people laughing at this guy’s inventiveness.)

    • Reply Johnny March 13, 2013 at 10:32 pm

      Hahaha. That’s awesome. I wouldn’t be surprised if a few people at least tried to toss a quarter at him.

      We noticed there weren’t nearly as many panhandlers in Boston as NYC. Actually… now that I think of it, I don’t know if I’ve ever seen as many homeless people in a single location as we used to see near Boston Common. They were always milling about near the 7-Eleven and NE entrance.

  • Reply KK @ Student Debt Survivor March 13, 2013 at 10:25 pm

    What a beautiful story. Sad I’ve never bumped into this man. Maybe on my next ride.

    • Reply Johnny March 13, 2013 at 10:33 pm

      Lisa (the very first commenter) said her husband encountered him a few weeks ago, so it sounds like he’s still around, brightening folks’ days. Go find him and let him know I’ve still got my portrait.

  • Reply sandra March 18, 2013 at 3:50 pm

    I was doing my usual produce shopping at the 99 cent store when I look over and a large-ish man was berating a cashier and had is cart put out in such a way no one could pass near the exit. it seemed people were trying to wait him out so they could pass. I noticed a woman with a full cart headed that direction and asked my self what could happen next. well the man acted the same taking impossibly long and I overheard the woman with the full cart Politely ask the man to move his cart and he did, but not with out berating her even more nastily than the cashier. This woman held her composure and didn’t even answer back even though I’m sure she had a wave of emotion go through her.when I finally got out side I looked all around for her and it was beginning to rain. I wanted to apologize for the way that man had treated her. when I found her I saw her situation and that full cart wasn’t just groceries and wondered if I should wave off my initial feelings. But seeing her didn’t change that she was human and deserved to be looked in the eye and offered a smile. I only wanted to help more. I kinda chickened out a bit by giving her money through my car window since it was raining. she was grateful and told me her story in a quick nut shell, she only wanted to be understood and even asked me a few questions about my self. she had lived in this area with her husband her adult life and owned a home and there truck driving business had gone under. She did eventually go off on a rant after asking about my religious views and telling me how a “boy and a tree” weren’t possible. So I goes to show you- If you will but only take the time to look, then you will find something to like about everyone.

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