Panhandlers of Harvard Square

In 2011 the panhandlers in Harvard Square seemed particularly young, particularly sad. My goal was to paint 15 or 20 of them by the end of the summer; I painted 19. Laura Montgomery of the Bunker Hill Community College Art Gallery was kind enough to offer me a one man show and I'm grateful for her interest in my work.

My approach remains the same. I'm torn on the issue of giving money to beggars, but I have no problem paying for services rendered, so by paying $10 to let me set up my french easel and paint them I feel these folks are earning a fee, not just accepting a handout. All paintings are done from life, on site, plein air and alla prima, and take between one and four hours to execute. Additionally, as I've worked more and more on this series it's turned not only into an art project but a socioliterary one as well. Over the course of the past few years I have become aware of some continuing sagas, like the tragic love story of Gary and Whitney or the mysterious Rabbi, and these continuing chapters are included as notes where appropriate. For the most part I have not updated the stories as originally recorded, but appended updates as addenda at the end of each description.

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Slim and Merlin
Rosie and David
Whitney 2012 Susan 2012 Ronald 2012 Christina 2012 Max (Maxine) 2013 Melvin 2013   Justin 2013 Bea 2013 Michael and Lord Paladin 2013 Angel and Sincere 2013 Jason (Cowboy) 2013 Nellie and Billy 2013 Jim 2014 The Lovebirds 2014 James 2014 Lexxie 2014 Mike II   2014 Dennis 2014 Alistair II 2014 Sunshine 2014 Kitty, Joshua and "Dirt" 2014 Burton 2014 Carl 2014 Erich 2014 Gary and Whitney 2014 Joe 2014 Ashanti 2014 Mars 2014 John 2014 Frank 2014 Maria 2014                  
I did this painting in the fall of 2010. His name is Chuck and he hangs out in Harvard Square near the T stop. He was very obliging when I asked him to pose for me, which encouraged me to undertake this project. Chuck has a stoma and can't really talk.

Colleen was the first model to pose for me in 2011. There were, and still are, a lot of very young street people, a lot of "passing through, need to eat" signs. I'm sorry, I don't know her story, I wasn't really documenting her as much as responding aesthetically and emotionally to her predicament.

9/29/2013 - I am informed by a panhandler that Colleen died last night of exposure and a drug overdose. Very sad news.

Carrie was pretty obviously strung out. At the same time she was quite successful in terms of collecting money. There is obviously something very appealing about her that spoke to passersby. I hope I've captured a little of that.

NB: Ken informs me that Carrie is now clean and sober. She still panhandles, but she is no longer using.

Gideon collected absolutely no money while I was painting him. Despite his sign and tin cup, he claimed not to be panhandling, but "fortune telling" instead. Gideon kept up a constant stream of talk to no one in particular while I painted him. He seems to be fairly disturbed, which may be why no one gave him any money while I was there.

Richard actually attached himself to me in Mansfield, before I got on the train into Boston. He followed me to Harvard Square; I'm not sure where he was originally headed. He was obviously hopped up on some kind of medication. He was also the worst model I'd had to date: wouldn't sit still and bailed on me after an hour and a half. He had a shtick ("Hey man, you dropped something! Yeah, you dropped your smile! Go pick it up, man!"). Instead of asking for money, he held out a dollar bill and asked people if they could make change. Needless to say, he was a very successful panhandler.

Richie was very soft-spoken, very intent on his own art. He was doing careful pencil drawings from photographs the whole time. I actually found him kind of scary looking when I saw him around in the Square earlier, but I was completely wrong. Apparently I am a terrible judge of character.

NB: Three years later, Richie is still a fixture in the Square. He frames his drawings and apparently is selling them. I'm jealous.


Kelly was working on a needlepoint outside the international newspaper place next to the Coop. She knew who I was, so I guess my project is becoming known among the local panhandlers. She introduced me to her husband. After I paid her an elderly woman who seemed not quite right in the head came up to her and asked for money. Without a second thought Kelly gave her one of the fives I had just handed her. Maria is the panhandler Kelly gave money to. She was very happy to pose for me, described the ten dollars I offered her as "the easiest ten bucks she ever made." She was concerned the painting would end up in the local newspaper–I told her no, hopefully, just a local gallery. She actually yelled later at a tourist she suspected of taking her picture. Her come-on was a monotonic "Spare charge please--spare change please," with mixed results from passersby. Her mood switched back and forth from pleasant to paranoid. At one point she yelled at a passing bicyclist with whom she had apparently had a run-in earlier. She threatened to call the police on him, he threatened to have her put away.  

Gary is a Desert Storm vet. He did not solicit money and seemed to be nodding off. At one point I asked him if I was preventing him from making money. He smiled and said no.

A group of Chinese tourists stopped and asked if they could take a picture. I said I didn't mind but they'd have to ask Gary for permission. I then suggested they make a donation. After sitting very quietly all morning he suddenly became aggressive and suggested they could have given him more money. Gary's wife Whitney stopped by. Another panhandler, she looked terrible, was wearing a face mask and had her head shaved. She said she was going in for chemotherapy for her cancer. I'll try to paint her soon.

NB: Nearly a year later, I finally painted Whitney. See her painting near the end of the 2012 section.

Kimberly was stationed next to the entrance to CVS. She asked every passerby for spare change and if they went into the store without making a donation, would ask "Maybe on your way out"" Most people gave her their change as they left, and she was getting a handout every two or three minutes. I wonder if there's any competition for what is obviously a prime panhandling location.

I didn't spend as much time on this painting as I should have, but as it was I stood in the blazing sun for an hour and a half to get this portrait. Given her sunny disposition, that seems appropriate.

NB: Ran into Kimberley in Harvard Square after I painted Ken. She asked if I remembered her and I said "Sure, you're Kimberley." I think she was a little surprised I remembered her name.

Anthony's sign read "Too Ugly to Prostitute, Too Nice to Be a Pimp." I had actually tried to avoid painting him because his rap seemed a little too "trustafarian" to me, a little too much like play-acting. However, once we started to talk I was again reminded of what a terrible judge of character I am; he was sweet and needy. Anthony had recently lost his job as a security guard. He had been teamed up with another panhandler in the area using a sign that read "Bad Advice: $1." However, they had had a falling-out, the other guy had kicked Anthony out of his apartment and he was now truly homeless.

Anthony really liked his painting and was talking about buying it from me. I kept putting him off, until I realized he wanted to pay me back the $10 I'd given him and take the painting in return. Then I told him I wanted to keep the painting with the others I was doing, as a set, and he seemed to accept the idea.

Daniel was sitting next to the elevator in the well in front of the Harvard Square T stop. He was very enthusiastic about having his portrait done and offered to pose for free. He is one of the outgoing, chatty type panhandlers, and so was reasonably successful in his efforts. Daniel was concerned about staying out of the sun because of his medication. He was also initially concerned that some of the other street people in the area would give him or me a hard time; this did not materialize. However, at one point Maria walked by and they more or less hissed at each other like a couple of angry cats. He told me she had had him arrested for threatening her.

Lanay's sign offered tarot readings for $5. She was hesitant at first about posing for me, but then agreed. Lanay was deeply involved in an imaginary conversation which involved bemused expressions, full-throated hug-yourself laughter, winks, and "no you are" double-handed finger pointing. I believe she rehearsed the same scene three or four times at least while I painted her. Needless to say, no one gave her any money, although several people handed her food and drinks.

When I asked her her name, Lanay hesitated again. I asked her to spell it and she gave me two different spellings. I suspect Lanay is not her real name. Perhaps it is her identity in the fantasy world she inhabits.

Keith has a thing for the ladies. His taste was so impeccable that I soon found myself being distracted by a reliably shapely female form receding from view whenever I heard him say "Oh young lady, I like how you make that dress move!" He also freely dispensed advice to many of the street people. "I've been here six years," he told me. "I'm everybody's uncle." He advised a sad-eyed young black woman at length to head home to her parents. She spoke not a single word the whole time. Afterwards he winked at me and said "If she goes home I get her spot." At one point Keith showed me his baggie of prescription medicines. "Congestive heart failure" he told me, and laughed. More than any of the panhandlers I've met so far, he seemed to be having a wonderful time and did not regret his decision to live on the streets.

NB: A few days later I was painting Sean and Keith stopped off, He was in a lot of pain and said there was no way he could get more pain medication anytime soon. Perhaps I was a premature in suggesting he did not regret his decision.


I painted Sean on Labor Day. He complained that the panhandling was slow and people were not being generous. He was happy to accept my $10 and I suspect it made up the bulk of his take that day.

John was very quiet, he did not ask for change, just shook his cup. Nobody seemed to be giving today and I started to get worried that my presence might be interfering with John's panhandling. He told me no, things had just been very slow lately. Things picked up towards the end of our session.

A little bit of old home week today. I ran into and chatted with Gary, Kelly, and Keith. I asked Gary if his wife was still interested in posing. She was , but wasn't feeling well today and stayed home. Keith was feeling better. Kelly asked me if I'd found a venue to show the paintings in. When I told her I thought so, she became very excited for me.

Frenchie runs the $2 book stand on Mass Avenue along with her friend Ken. Technically I shouldn't have painted her; she's not panhandling. She is homeless though and I've been wanting to paint her portrait for a long time now.

Frenchie is an endless font of anecdotes about her and Ken's run-ins with the City of Cambridge and the local bookstores. They've won every court battle with the City though and the book stand is now open 24 hours a day. She and Ken live in a tent in the woods somewhere outside Cambridge. She told me they spend the winters there, thanks to a propane stove. Quite a character.

NB: October 2012. Sadly, the outdoor bookstand has been gone for some weeks now. See the description of Ken for more info.


Smiley's real name was Steve. He was in town after a trip to New York and Philadelphia and was on his way back to Vermont where he expected to be a ski lift operator come December. His ultimate goal is to move to Colorado.

Merlin (in the rear) and Slim were hanging out outside the CVS next to the Coop. I asked Slim to pose for me but the composition with both of them was too nice and since they were obviously friends, I asked Merlin if he would pose too even though I didn't have $10 for him. I said I'd give them whatever I had in my pocket (it turned out to be $16) and they readily agreed. Their come on was "Spare change for Arizona Iced Tea... Spare change for Arizona Iced Tea..." When they'd collected enough Slim went into the store and bought two Arizona Iced Teas. They then switched to "Spare change for pizza... spare change for pizza..." I have no doubt that day they lunched on pizza.

While Merlin and Slim were quietly taking care of business other dramas were swirling around them. An older panhandler whose name I didn't catch was standing next to the CVS door despite the owner's repeated requests for him to move away. He called the police, and it developed that the policeman who showed up to send the older panhandler on his way had arrested Merlin and Slim the day before. The cop grinned and said to me "It'd sure mess up your painting if I arrested those two" and I answered, 'Yes, you would." He didn't. Perhaps the saddest conversation I had all day, however, was with a young panhandler who liked the painting and wanted to pose. He said "Hey ma, come look at this!" His mother, another panhandler came over to look and he confided to me "My father's the guy on crutches panhandling down the street."

My first panhandler painting of 2012. Ken runs, or ran, the sidewalk $2 book exchange on Mass Avenue with his wife Frenchy (see earlier). He closed down the sales element of his "bookstore" last fall, turned it into a book giveaway (apparently he has 30,000 books in storage to get rid of!) and is now simply panhandling on the street in front of his old spot. His reasons for closing down the business were increased costs for buying books and competition from Kindles and the like. Frenchy was quite ill this winter, the encampment where they had been living was shut down by the state police and Ken was able to wangle a permanent room in a shelter for the two of them. He's now trying to get on SS disability. I suspect he sees it as a matter of honor and self-respect to be "pulling a fast one" on the authorities. He is one of the hardest-working lazy men I know.

An attempt to back away a little from my subjects; I feel the last few paintings have been a touch too intimate, to the point that the space is getting too shallow and flat. Here I've caught the gesture I think, and placed Mike firmly in a three dimensional environment, but at the cost of the portrait. Mike's face is so unique though that, as he noted, anyone on the street who knew him would recognize his face immediately.

Alistair is Scottish. He's been in this country for 13 years, following the Grateful Dead and other bands back and forth across the country, and his accent is almost gone. Until recently, he told me, he had long hair and a beard. I've indicated his tattoos just a little. Alistair divides his time between Boston and San Francisco, and seemingly has not seen much else of the country. He's been in a few fights, as evidenced by a long scar on his cheek and his multiply-broken nose.

NB: May 2013. Alistair is still in the Square, in fact was here all winter. He's looked at this web site and informed me of a few corrections: he's been in the States 13 years, not 19, and he received his scars and broken nose in Scotland.

Nellie was sitting with her friend Bob in the same location as I painted Merlin and Slim last year. The spot was on "loan" from another panhandler whose name I didn't catch. I paid him three dollars essentially to go away, and he seemed quite gleeful and triumphant at the coup. Nellie was badly sunburned and I gave her some sun tan lotion. She alternated between brassy, "creative" come-ons and a simple "spare change please." She told me she felt embarrassed to be panhandling and wouldn't request money from people with children. On the other hand, one of the most touching moments of the morning was when a passerby gave his two-year-old a dollar to put in her cup. About fifteen minutes into the painting session Nellie requested her money in advance, then sent Bob off to buy a 40.

Although this is a nice spot to paint I will have to avoid it in the future. A policeman came along and made Bob and Nellie move, just as happened in the Merlin/Slim painting session, throwing a monkey wrench in my painting effort. Live and learn.

Michael has been sitting outside the T Station entrance for quite a while now and has asked me repeatedly to paint him. He is a little older than me; he turned 56 in May. He holds a "Seeking Human Kindness" sign and is a polished and eloquent speaker. I'm always concerned my being there will interfere with my models' panhandling activities, but he told me business was actually better with me there.

Usually I pick up people's stories in bits and pieces during the course of a painting, but this time a passerby stopped and said to Michael "Let me look at your eyes." Satisfied, he gave him a $20 bill with the comment "I used to be homeless too. Now tell me your story." Michael's story is that he was working as a construction supervisor when he had a minor stroke. When he got out of the hospital, he had no money, no job and no home. His goal is to save up enough money to move to Montana where the economy is booming and there are high salary jobs to be had in the oil industry. I wish him well.

Rosie and David were sitting on a blanket near the Coop. Their shtick was their three guinea pigs which got a lot of attention from passersby; note the one on David’s neck. I hadn’t budgeted for two models but Rosie was very grateful to get $15 from me. When I turned around I saw I was being watched by an older street person who had a sign: “Old Books / 19th Century Newspapers $5.” Naturally I went over to check out his wares. We had a little conversation about old coins and he forced a 1943 steel penny on me. Also had a chat with some guy from the local community TV station who asked if I wanted to do an interview. Recognition! (Note: nothing came of it.)

Laurel was one of the saddest looking panhandlers I've seen. Her sign stated that she was a homeless mother of four and a victim of domestic violence. I gave her my little speech, which is designed to reassure my subjects that I'm not planning anything creepy and establishes a financial basis for a transaction. In her case it went like this:

"Are you going to be here for a while"

[wordless nod]

"Would you like to make ten dollars""

[More vigorous but still wordless nod]

"I am doing a series of portraits of panhandlers here in Harvard Square. I would like to set up my easel and paint you. It takes about two or three hours."

Laurel became progressively more forthcoming as the painting session went on. She told me about her ex-husband, who beat her until she left him, and her recent boyfriend whom she had known since childhood, who suddenly became abusive after she moved in with him. At one point she mischievously flipper her sign around to show she displayed to guys who propositioned her:

"I am not a whore, asshole."

When I finished the painting Laurel looked at it and said "Yep, that's me."

I finally painted Whitney, Gary's wife. We've had a few missed connections and this time I actually waited an hour and a half to paint her while she ran an errand. Whitney is very ill with cancer. While she was away, Gary filled me in on the events of the past few weeks. First of all, he was arrested and spent 60 days in jail on what he maintains were trumped-up charges. While he was away, Whitney was robbed at knifepoint of her Social Security money, then knocked unconscious. What is even more disturbing is that apparently I've already painted a portrait of her alleged assailant. As I've said before, I am a terrible judge of character but this is a little scary.

Whitney also broke her foot, then decided you didn't like the cast and took it off. As a result, she needs to go back into the hospital and have her foot re-broken again so it can be reset. Gary informs me that her cancer has spread to her brain and down her spinal column. The doctors, he says, are unsure why she's still alive. Gary is no longer allowed to stay with her in her rent-controlled apartment and has been fired from his 40 hour a week job as her caretaker. He's been sleeping on a park bench near the river and is contemplating suicide after Whitney passes away.

On the plus side, I also was present for the following conversation:

[A passing panhandler]: "Have you heard" The Rabbi's back in town!"
"The Rabbi" Really""
"Yes, I saw him the other day."

I asked "Who's the Rabbi"" The Rabbi, I was informed, is a local legend, a mysterious stranger who dresses like a Hasidic Jew, isn't around between Friday evening and Sunday morning, and hands out twenty dollar bills. He makes a point of creeping up without being seen, stuffing a $20 bill in the panhandler's cup and then rushing off before they can see his face or thank him. I said that makes a certain kind of sense, because there are levels of charity in Judaism, one of the lower levels being a charitable gift in which the recipient and the donor are known to each other, In the second highest form of charity the donor and the recipient don't know who the other is, and in the highest form the recipient is lifted permanently out of poverty by a loan or partnership enabling him to start his own business. If the Rabbi doesn't want to be seen or thanked, I told them, it could be because he's practicing one of these higher levels of charity. 

Still learning important lessons... like make sure the model can hang around for more than 45 minutes. I asked "Are you going to be here for a while"" instead of "Will you be here for the next hour-and-a-half to three hours"" (Susan needed to leave, she told me, to get in line for a shelter bed.) Perhaps it was the sudden mad rush but I think I was on the money with the likeness, the expression and the purely painterly aspects of doing this portrait,

Unfortunately I didn't have much time to chat with her but there seemed to be more bad news in the panhandler community. Two passing by complained about getting robbed in the past few days, one of his cell phone, the other of a cup full of cash that mysteriously vanished. The consensus was that some bad apples had shown up lately among the transients.

Ronald was hanging around outside the Grafton Street restaurant with his shopping cart. He seemed to have everything under control. He told me he considered panhandling a job, one which he arrived for around 6 in the morning and did not stop working at until he had made at least a hundred dollars; in fact, when we were done he pulled out a roll of currency and proudly counted it off to me. He has been out of prison for three years after spending most of his time there since 1979.He rents a room in a local shelter.

Ronald considers himself a biblical scholar and was eager to proselytize me. I told he was welcome to try but that when he was done I intended to destroy his faith; he laughed. He believes himself to be descended of one of the lost tribes and was wearing a Star of David and an ankh around his neck. He had a few theological points he kept returning to, but overall, I'd say our debate was a draw.

NB: Saw Gary again. He was wearing hospital scrubs and told me he had suffered a heart attack, then been robbed of his clothes and money by the EMTs. Whitney refuses to let him sleep alone in the park and joins him their at night, which is good for neither of their health. This does not bode well.

Given the weather, this is probably the last panhandler painting of 2012. To be honest with you, I'm a little disappointed in this piece, and if this were purely an art project, which it started out to be, I would probably omit this painting. But this exercise has turned into more than a simple art project; it has taken on sociological and even literary connotations, and so, for the first time, a painting in which I feel my commentary is of more value than the painting.

Christina has been in the Square for a week or two now. She holds a sign which reads "Family in Need," and reads the Bible. She was very eager to pose and very eager to talk.

Her story is that she has a 16 month old baby. Her mother had come out from Nevada to pick up the child, but Christina and her baby daddy were trying to raise the wherewithal for tickets to Las Vegas. She told me her street name is "Penguin," as in the Batman villain. Then her story started to unravel, at least from my point of view.

First of all, for someone who was ostentatiously reading the Bible and trading on people's sympathy for an unwed mother, she had a mouth like a longshoreman. Her panhandling technique was more West Coast-style, involving as it did loud and enthusiastic cursing of anyone who ignored her pleas. She had an immediate opinion on anyone who did not make a contribution, and since no one did while I was there virtually all the women and many of the men passing by were subjects for her scorn. She did not approve of the other panhandlers, who she considered liars and phonies compared to her own verifiable claims to sympathy, and she found the Harvard Square passersby cheap and ungenerous. On the other side of her sign it read "On My Way to Hippie Hill."

In the final analysis, there was something rude and dishonest about Christina, something calculated and inauthentic, and I believe that came through, unfortunately, in my painting. I realize I am a little too trusting and believing of the people I've met and the stories I've heard, but, with the exception of the panhandler accused of attacking Whitney, whose lies, if such they were, were pathological, and a couple of other examples of transparent pleas for sympathy, this is the first time I've really felt someone I was painting was actively trying to deceive "the marks," including me. Perhaps a sad conclusion to the 2012 painting season, but an important if disheartening lesson to learn: the poor and the homeless are just like you and me. They have their own saints, their own sinners, their tragedies and their comedies, their Romeos, Othellos and Iagos, their Barts, Lisas and Homers. There, but for the grace of God, go the rest of us, and perhaps that's why we find them so hard to look at.


First painting of 2013 and I can't decide if I like it or not. Max was camped out next to the Coop main entrance. There's a pit bull buried under that pile of bags next to her–I didn't see it until after I finished the painting, when she got up to use the bathroom and he emerged to see where she went. Pit bulls seem to be the dog of choice for panhandlers this year. Max says she has two others, currently with other young beggars in the area.

We didn't really chat much, but she seemed to attract a certain kind of young, pimply, greasy-haired donor. I'm learning more about panhandler etiquette too. A woman sat down across from the fellow selling his paintings and several panhandlers yelled at her about squatting on other people's territory (she didn't leave, though). I was also visited by Bea, one of the older panhandlers among the latest arrivals, who delivered a stinging criticism about how I was reading my own feeling into Max's pose. Perhaps she's right. I'll paint her later.

Melvin hangs out a lot with Alistair near the Harvard Book Store and that's where I found him Sunday morning. Alistair had just come back from the laundromat, He complained that the usual place in Central Square had closed down and he had to walk all the way to Inman Square to find an open laundromat. Life on the street seems full of these petty indignities. Melvin and I headed down to the alley behind the Coop, where he set up shop on a concrete bench. He was as chatty as Max had been reticent, so I got the whole story--the years of working for the City of Cambridge Parks Department, being a truck mechanic, taking care of his dying mother, and then the nervous breakdown and ending up on the street. Mel's big beef was with the street musicians, who he felt had an unfair advantage, since they were licensed and could set up wherever they wanted whether or not it impacted the panhandlers; plus, people tended to walk right past the homeless if there was a street musician to give their money to. I took the opportunity to ask him about how prime panhandling locations were apportioned (first come first serve, but very often two beggars would partner up to make sure prime locations stayed under their control) and whether he'd heard of "the Rabbi," a character I find fascinating. He confirmed the Rabbi stories. As I was finishing up a pale young street musician in a white shirt, jacket and tie set up behind us and began to expertly play the didgeridoo.

Sad news. Melvin passed away last week. Please see the 2014 painting of Alistair for a discussion of his death.

RIP Melvin Emery Jenkins, November 16, 1955 - June 16, 2014


Justin is very young. He likes to fish in the Charles but has never caught anything worth eating. Still he wants to keep at it. His last reel broke.

Justin wasn't feeling well or up to chatting up the passersby. As a result he did not collect much money. A young woman, Regina, stopped to talk first with me ("I'm a photographer, my boyfriend is a surrealist painter") and then with Justin. I shamelessly eavesdropped, but Justin's story was essentially that he had moved here from points unknown with his girlfriend, she had kicked him out of her apartment, and he ended up on the street.

I was painting Nellie and Billy the other day and Bea stopped by and asked me to take her picture and story off my web site. Out of respect for her wishes I have done so; however, I am not happy about this and I am going to have to start asking people in the future whether they object to my posting their painting on this site. If the answer is no I will not paint them (or pay them!). I certainly am not painting these portraits in order to hide them away forever.

If you wish to see the painting I did of Bea and read her story, please email me and I will be happy to send you the information.

I ran into Kelley, who I understand is no longer homeless but still hangs out in the Square doing needlepoint. I gave her ten dollars in keeping with my decision to "spread the wealth" from the $600 I got from the Globe for the panhandler article. Later another panhandler I painted last year showed up and I gave him ten bucks too. By the time I paid my subjects fifteen bucks I was pretty broke.

The guitarist in this painting, Michael, was setting up to play and invited me to paint him, so this piece is a little off subject and technically not part of the panhandler series, I asked him his friend"s name and got the answer, after a brief pause, "Lord Paladin," As I started to set up an older guy sitting said to me "You can"t stand there! You"ll block my jewelry." I apologized and moved. Later he chatted me up; turned out to be a retired cop (he showed me his badge) and the jewelry was by his late daughter, who sad to say had died of an overdose. He was selling it kind of as a memorial. He showed me enough scars to make me queasy and asked me to be on the lookout for anyone bragging about a recent attack on a Cambridge police officer. Apparently a local cop was waking up the street people in one of their hangouts behind the Coop when someone snuck up and clobbered him with a brick. He"s recovering in the hospital but it"s one more reminder that there are good and bad folks among the homeless as with anyone else.

I started out painting Angel. Sincere, the woman in the back, and another young panhandler came along shortly. Since I painted a little bit of Sincere, I gave her five dollars as well. If I had waited five minutes longer the painting would have been about her--she spent the whole time watching me and I would have gotten in a better portrait. Oh well...

Gary and Whitney came by and informed me that Colleen, whom I had painted back in 2011, had died of exposure and a drug overdose the night before. Sad news indeed.

Cowboy was extremely intoxicated. Nevertheless, he collected quite a bit of money just sitting there and nodding off. He’s apparently quite well known and liked on the street–a dozen people stopped off to say hi or hang out for a while.

I originally planned just to paint Billy but Nellie practically begged me to let her pose. She wasn’t too happy about sitting on the ground, and then became concerned when I said it would take about two hours. I said I’d paint her first. When I was about three quarters done I said “Wait a minute, haven’t I painted you before?" She took her ten dollars (luckily I’d grabbed a little extra cash before I left that morning) and was off like a shot.

I’ve seen Billy around and obviously he’s quite the character. I don’t know if I’ve done justice to his outfit or to his waxed mustache tips. His hands seemed to be cramping up as he played the guitar, but he said it was because he’d intervened in a fight between his then-roommate and the roommate’s girlfriend, and ended up at the hospital.

First panhandler painting of 2014. I've noticed a bunch of new faces in the Square in the past few months when I come in during the week to work, so I came in on a Saturday hoping to paint one of these newer, younger transients. Alas, at 11 a.m. on a Saturday, none were to be found, although they're all over the place and at all times during the week. I did see Gideon, whom I had painted back in 2011, and gave him an extra ten dollars for his trouble.

Jim is one of the Harvard Square regulars. He sits in a wheelchair outside the bank next to the T stop and asks people to make a contribution to wheelchair basketball. After I gave him my usual shtick -- "Would you like to make ten dollars" I'm doing a series of paintings of panhandlers in Harvard Square, Can I set up my easel and paint you"" -- I added, "You are panhandling, aren't you" I don't want to insult you if you're legitimately raising money for wheelchair basketball." He smiled weakly and answered "Panhandling, soliciting, begging--it's all the same thing, isn't it""

I made a point of getting the portrait down as soon as I could, since we were at a critical juncture on the sidewalk and mildly impeding foot traffic. Just as well, since a busker set up in the Well, attracted a crowd, and created such a mess I felt obliged to close up shop a little early and get out of the way. Incidentally, Jim seems to be doing quite well for himself as the panhandlers go in the area. I'd say he easily collected ten or fifteen dollars from others in the hour and a half I painted him. That may not sound outstanding but it's as good as I've seen in the past few years.

Justin (whom I painted last year) and his girlfriend Lauren. Justin had proposed the night before, Lauren had accepted, and their sign reads "Newly Engaged Need Motel to Celebrate." Lauren was almost absurdly cheerful at first, but became progressively glummer as the day progressed. She couldn't understand why their sign wasn't eliciting more donations (they changed the message later that day), or even garnering them congratulations for their engagement. They discussed their plans between smooching, which involved getting an apartment and one of them working while the other went to school, then vice versa. Lauren had fled her abusive husband, run into Justin up in Vermont, then followed him here. She suffers from hypoglycemia, which explains her deteriorating mood.

Spoke to Ken the other day. He and Frenchy are in an apartment (as he pointed out, his sign no longer referred to them as homeless). Their various SS, disability and other payments cover the rent and utilities, but not food, which was why they were still panhandling. Ken has been diagnosed with diabetes and is beginning to suffer foot complications. He told me his one luxury was a Comcast cable/high speed internet connection, and that he was playing two to twelve hours (!) a day in an on-line multi-player game that had the word "Empire" in the name. I guess everyone needs a hobby...

James sits in a motorized wheelchair outside the Campus Center. He is severely disabled and has only one leg. His speech is almost impossible to understand but he makes an effective pitch by simply smiling and waving. James seemed eager to chat and through a combination of repetition and shakily spelling words one letter at a time on his pants leg he told his story, even essayed a joke. "A pimp," he told me, pointing to himself. "A pimp with a limp." He liked to fish, he said.

James lost his leg in a motorcycle accident in 1989. He wasn't wearing a helmet and alcohol was involved. He spent six months in a coma. James seems to be there mentally but he is trapped in a radically impaired body. I assume he has access to shelter and physical assistance of some kind. James is 52.

For about 15 minutes I was haunted by an Asian tourist standing about two feet behind me watching me paint. I might have asked him to move but I firmly believe if you're going to paint in public, you have to put up with whatever comes your way. Besides, he kept repeating "You are a genius, a genius!", which is nice for the ego and who was I to disagree" It seemed to be my day for that kind of thing because earlier a very small Asian boy had stopped to look and told me solemnly, in a very grown-up voice, "That is very well done."

Incidentally, if anyone ever writes a newspaper article about me and decides to call me a genius--I'm waiting--I hope he'll do it in a certain way. I'd like him to say, "Hats off, gentlemen, a genius." Yup, that's it. "Hats off, gentlemen, a genius."

Lexxie was working on a sign -- NEED MONEY TO FIX BANJO -- when I stopped by. She looked at me a little askance but Billie, whom I'd painted last year was sitting right there and I said "Go ahead, ask him if I'm legit." Satisfied she would get her ten dollars Lexxie put away her sign and got busy sewing disintegrating clothing items back together. With her skinned knees and rasta hair, she gave off a distinct Desperately Seeking Susan vibe, which seemed to have her red-haired hippie companion captivated. At one point he took off, then came back with a set of pliers still in their oystershell. Lexxie was genuinely grateful and gave him a hug, then got to work fixing her banjo. She expertly strummed a few chords–or whatever it is you do with a banjo–then put it aside and went back to her sewing.

Lexxie's little dog liked me. You can see his butt next to her messenger bag but he ended up under my easel, then next to me, then on top of my feet. I thought I was going to have to take him home but he came to his senses.

Several of the youngish hippie types were hanging around and one of them asked Lexxie if she wanted to drink a 40. She gave me that look that said "I'd rather be elsewhere."  and I asked, "If I give you the ten dollars are you going to jump up and run away"" She smiled sheepishly.  I gave her the money, she handed it to her friend who scampered off to make a the purchase. "Hey! I guess I can stick around," she said and I was able to bring the painting to fruition.

Odd, somewhat frustrating day yesterday. I decided to go further afield and ask panhandlers around the Commons to pose for me, but when I got there, nobody was panhandling. I saw plenty of obvious homeless/distressed people but nobody whom I could ask "Can I paint you while you beg"" I suspect the Boston cops have put the kibosh on the cup-shaking I remember from the old days.

I finally gave up and headed into Cambridge. Got a burger at a restaurant and on my way out a young black women (her supervisor or trainer standing a few feet away) stopped me and gave me a canned spiel about her involvement in something with Young Entrepreneur in the title. If she met her goal she got a thousand dollars. "I'm looking for a hand up, not a hand out," she told me, repeatedly. I managed to pin down her product--three, six or nine magazine subscriptions--and after some wheedling, the price: $79.95. I said, "Look, I'll be happy to donate $20 for whatever cause you're pushing but there's no way I'm going to spend $80." Without a word she turned on her heel and walked away. When I left the restaurant (what were they doing in there anyway") the two of them walked out behind me and proceeded to discuss her interaction with me. "If he'd offered $30 we might have been able to do something," said the supervisor.

I now went in search of a model. I was turned down by two separate panhandlers I approached, a new experience for me. I finally was heading over to a spot I'd scoped out as a landscape site, when I saw Mike.

Mike had a cardboard sign and was working the cars stopped at the stop light where Garden Street merged with Mass Ave., weaving his way through traffic. I had painted Mike in 2012 but at the time I had decided to try something more full figure and I didn't really have a portrait per se. I called him over and we made a deal. He hid his sign away somewhere, then met me at a nearby park bench. Mike didn't talk much, certainly not about himself. Various people stopped off to chat and three of the street people said "Paint me next!" Feast or famine. Just as I was finishing an old high school friend of Mike's appeared and they had a nice chat.

Dennis is Kelly's husband. He is not technically a panhandler, nor is he homeless, but he is "street" and has hung out in Harvard Square for many years. He did not turn down the ten dollars I offered him.

Alistair has been after me to paint another portrait of him for some time now. He needs the money. He has been extremely upset about the death of his best friend, Melvin, so I decided to paint him again, if only to memorialize his quite impressive beard. However, as further proof that no good deed goes unpunished, while I was able to get in a good drawing of him, he started to chat with another panhandler and spent most of the session looking away from me. I try to work around this but I'm afraid the painting is not what it could be.

As I said, Alistair has been quite distraught at the death of his friend Melvin. Melvin has been in and out of rehab since I painted him. He passed away suddenly of a heart attack last week. First Church held a memorial service for him Saturday, with another one scheduled at a different church in a week or two. The church contacted me and asked if I could lend them the painting I did of Melvin so they could display it at the service. There are no other photos of him. I brought the painting in, stopped off at Dick Blick and bought a kit so I could frame it, then dropped it off at the church.

The obituary editor at the Boston Globe contacted me and asked for more info on Melvin. I told him to contact Alistair. He's going to get a full blown obituary in the Boston Globe.

Amazing, isn't it" This guy lived under the radar and on the streets for years and nobody gave a crap about him. Now he's dead and suddenly the subject of massive attention. What a sad commentary.

Sunshine is almost exactly my age. She has three children and several grandchildren. When I was had finished I asked her, "Are you sure you don"t want to tell me your real name"" but she assured me she had had it legally changed some time ago. I said, "You"re too young to be a hippie," but she"s rather proud that she is one.

Sunshine"s main gripe was the chirpy, cheerful clipboarders shilling for Planned Parenthood the whole time we painted. She feels they grab attention from the panhandlers and I tend to agree. I asked. "Should I kill her"" but Sunshine felt this was excessive. As I packed up and left the nearest PP shill said, "Would you be interested in"oh, never mind."

I ran into Kitty on the subway headed into Cambridge. She had just arrived from New York and was fully equipped"with backpack, sleeping bag, and a monstrously huge dog wearing saddlebags whose name I forget but was, she told me, half Rottweiler and half pit bull. "Am I headed to Harvard Square"" she asked me. Yes, I told he, she was. We got off and she asked "where people my age hang out." I suggested the Pit by the T stop but she was accosted by Dirt ("Dirk"" I asked; "No, Dirt," he corrected me) who assured her he would show her a good time. I headed down the street but didn"t see anybody I hadn"t painted already. (Why is that" I see dozens of panhandlers"I"d like to paint on weekdays when I have to work. Do they all go home for the weekend" God, I hope so.)

I headed back up Mass Ave and found Kitty and Dirt sitting on the brick pavement"next to the T stop. They had been joined by Joshua. I gave my usual spiel but told them I couldn"t afford to give them each ten dollars. That was no problem, they said. I ended up giving each of them $5.

Of the three, Dirt (the one in the middle) seemed the most presentable, with a neatly trimmed beard and college boy haircut. However, he turned out to be the most out of control. His act seemed intended mostly to startle passersby"suddenly singing patches of song in a loud raspy voice while banging his arms violently against his sides. He also told the same joke over and over ("What"s a pirate"s favorite letter"" "R"" "No, because of his love of the C!") and challenged people to "rap battles" for articles of their clothing. Kitty pulled out her ukulele and gave a mercifully brief non-performance.

She asked"Joshua to pick her up some gold and silver wire at the art store"there seems to be a lot of homemade jewelry-making and selling on the street these days"which involved a trip to Central Square. When he agreed she pulled out a thick wad of bills and peeled off a few for his use. I thought to myself, "I hope she doesn't do that too often," and then I realized what the dog was for. Indeed, many people stopped and wanted to pet him. "Is he friendly"" they would ask and Kitty would answer, "No, he isn"t friendly." He was, however, very well-behaved.

When I finished the painting Kitty got up to take a look. "Wow, that"s a lot better than I thought it would be," she said. "I hope you aren"t offended." "Why should I be offended"" I asked. "That was a compliment."

I came into town and did an actual landscape for a change (see the painting of Wigglesworth Hall in Cityscapes). While I was painting a disconsolate middle-aged black man dragging two suitcases on wheels behind him walked up and down the path several times. At one point he abandoned his luggage for several minutes and disappeared, but he came back. As I was finishing up I asked him what was the matter and he told his tale of woe: his daughter had been invited to an international conference to be held at Harvard University and they had flown in from Burundi the night before. They came here a day early to scope out the place and his daughter had asked a security guard for directions as to the location of the conference. She had followed the security guard away and not come back, and now he was looking for her.

I found a call box for the Harvard police and described the situation for them. After a few minutes a cop appeared and the African gentleman described his plight once more. A call came in; the daughter was found, and was waiting just around the"corner. Problem solved, good deed performed, I dropped off my painting equipment at the office, grabbed something to eat, then came back to paint a panhandler portrait.

Once again I had some trouble finding a suitable subject. I spoke to one of the panhandlers doing the walk-through-traffic-and-knock-on-people"s-windows-at-a-traffic-light shtick. He wasn"t interested but told me to be on the lookout for Burton. He was concerned about Burton because he had had a stroke and should not be walking around in traffic. I found Burton, who was both very happy to pose for me and actually, proactively posed too: kind of a pleasant experience after so many wandering eyes and bad models (I know, I bring it on myself).

I brought my painting stuff to work and was able to get out early on Friday and do a painting. Carl was sitting next to a young woman with a "Homeless and Pregnant" sign. She was not interested in sitting for me. Carl, however, was very interested and, like Burton from the previous week, actively posed for me. He told me he had some acting experience and compared the experience of sitting for a painting to posing"for"his head shot. A likable young man.



I again brought my paints into work on a Friday and left early to do a panhandler painting. Once again there was"nobody new"to paint. This is starting to piss me off. I chatted with Keith, who is not doing well physically, then kept looking unsuccessfully. Eventually I ended up in front of the bank next to my office. There were Gary and Whitney. They practically begged me to paint them so I ended up doing my third do-over portrait"of the season.

I"m not really that happy with it. It"s more about a set of circumstances"two people who once again"are homeless and now drag all their belongings around with them on a cart and in various bags and backpacks"than it is about two people. I"m unhappy with the portrait but reasonably satisfied with"the genre painting.

I guess I should relay"their story as they told it to me; it goes like this: they were staying in a room provided by an acquaintance who had lucked into a home by marrying an alien seeking a green card who was willing to pay to marry an American citizen. Once her residency was established she flew back to South America for a visit and it was while she was away that their friend invited them in. There they had provided their friend with necessary medication (I"m not quite"sure about this) at their own expense and to the tune of $2,000 when the wife suddenly came home and threw them both out. Needless to say, they are furious about this.

On the plus side, Whitney is in remission from her cancer and looks very healthy. She was trying to pin down a shelter and needed to make a phone call at a certain time, but the battery in her phone was dead. So she needed to go into Panera to plug in her phone, but the manager at Panera was very rude to her and followed her around everywhere, even into the bathroom, when she came into the store. They made a point of buying a cup of iced coffee there each day so they could establish themselves as customers.

While we were painting a personable young Asian woman came along and offered to buy Gary and Whitney food. She soon came back with a meal"and sat down with them to eat. She is one of those rare but charming slacker Asians, completely Americanized, casual and aimless;"an indication of what the children"of today"s obsessive Asian overachievers will be like. Eventually another panhandler of the "grubby youngster" variety arrived,"complimented her, and took her off with an offer to introduce her to the other"Pit denizens, with all of whom he was friends. "He"s not friends with them," Gary said after they left. "She should be careful around him." However,"she came back about an hour later, none the worse for wear. Then a young man stopped and asked them if they needed"foam cushions to use as bedding. He also provided blankets. I later saw Susan at the T stop with a new pillow still in its packaging, which I assume came from the same source. This is fairly typical of the largess the good people of Cambridge bestow upon their homeless population.


While I was painting Gary and Whitney we"were joined by Joe, who had suffered either a stroke or a head injury"I"m not quite sure as this information was conveyed in a whisper by Gary"and certainly his speech had"a characteristic"halting quality. He was very interested to pose and so the next day I came back and painted him.

Joe was not very forthcoming as a conversationalist. At the same time, he managed to extract quite a bit more information from me about me. At one point I pulled out my box of baby wipes, which I use to clean paint off my hands. "Can I have one of those"" he asked and I said of course. He proceeded to wipe his brow and his head and I soon offered him another one. By the end of the painting session he"d used four or five. When I was done I handed him a ten dollar bill and said, "Her"s your fee." Then I handed him the box of baby wipes and said, "Here"s your tip."


I received a paycheck from a client for a side job I"m working on (here"s a preliminary "cartoon" version of the animation if you"re interested:"v=ShqMXhH1-ds&list=UUr9lZ1yohWyc0PadP-yqo4w) so I"ve been feeling a little more financially secure and, hence, generous. On Saturday I came into"Cambridge and headed over to where Erich and his wife hang out, hoping to make good on my promise to paint the wife; they weren"t there, though. I wandered around a bit looking for a suitable model and handing out cash to the"regulars: James, Jim, Michael, Susan. I gave Michael a dollar and he said, "Oh, you must have gotten a residual!" Then I gave Jim a dollar too and Michael shouted, "Don"t give him money! He"s a fraud!" I answered, "So are you."

I found Ashanti sitting next to the CVS where I"ve painted so many panhandlers in the past. She was more than willing to pose and I started to set up, at which point she said, "Would you mind giving me the ten dollars now"" I said, "I"m sorry, but in the past when I"ve"paid people in advance some of them have bailed on me before I finish. You aren"t going to bail on me, are you"" She said, "I"m worried that you"ll bail on"me." I pulled out the ten dollar bill I had on me and said, "Ask anyone, I"m good for it. There"s no way I can sneak away, either, it takes me ten minutes to pack up my stuff." She said OK, but about five minutes later asked for the money again and I gave it to her after making her promise not to leave early, a promise she more or less kept.

I now make a point of holding off on drawing the portrait until I have a pretty good idea of which way the model habitually looks. After I set up my easel to one side of her Ashanti immediately started to look away from me, a problem I"ve encountered before. So before I started painting I moved my easel so I was standing directly across from her, waited for a typical pose, and started working. As soon as I had the drawing down she immediately started looking in the opposite direction, and ultimately I had to break one of my cardinal rules and ask her to look to her left as I had in the drawing rather than catching the pose on the fly. That was so successful I asked her to hold her arms still so I could catch that gesture too. Eventually she got up and sat down on the bench next to me, because, she told me, someone else had started panhandling down the way and two of them weren"t allowed to do it at the same time. As promised, she didn"t leave; she just stopped posing and I had to finish up her pants and arms"from memory.

The pickings seemed pretty slim"for Ashanti. Several people gave her money, but it looked like, at most, a quarter. One guy chatted with her for a while, left and came back from Starbucks with an iced coffee. Later, when she wanted to leave, she told me she had to go to Starbucks because he"d gotten her order wrong, then asked me for an additional two dollars. I gave her the sole dollar bill I had left in my pocket, and we each went our way.

Mars took the name Mars because he was, he told me, fascinated by the planet Mars. Mars has a distinct southern accent. He told me he and his brother flipped a coin when it came time to make a decision about where to go after leaving Kentucky, and the decision was Boston. His brother is gone, but Mars loves it here and has spent several years in the Harvard Square homeless community. He left an ex-wife and a daughter down South. Mars had originally gotten work as a tattoo artist, but was told his work was too old-fashioned and not up to Massachusetts standards, and so he ended up on the street.

Gary and Whitney have been hanging out outside my office. They still haven’t found a place, although they seemed to have a few leads. Gary almost gleefully told me about another Harvard Square panhandler who died, a young women I haven’t met who worked mornings at JP Licks. That brings the total of premature deaths I’m aware of to three, although Gary claims there have been at least a dozen. I haven’t been able to find any confirmation of this or statistics on homeless death rates in the Square. It’s been a tough year.

John volunteered to pose after I was turned down by his buddy–my second rejection of the day. John  sipped discreetly from a beer can otherwise hidden behind a trash can, alternated with a clear liquid drunk from a soda bottle in his other hand. He said the cops didn’t bother him; he was too good at hiding his liquor.

John was mostly mumbling to himself, but also enthusiastically appreciating the passing examples of female pulchritude. I said, “I used to work in a grocery store and when a pretty girl walked in we had a code over the intercom: Check out the ice. ‘Check out the ice in aisle three!’ You’re checking out the ice.” “I’ll have some ice,” he answered, “and some Pepsi too.

I buy a Spare Change News from Frank almost every week. He was standing in front of my office last Saturday when I came out and eagerly agreed to pose.

Frank is 63. He told me he had been an artist himself but nearly tore his thumb off when he punched a wall in a fit of rage and he could no longer draw. His brother, he told me, is a well known artist, and indeed he is–a successful comic book penciller when I looked up his name on-line.

Frank was in Viet Nam and spent several years as a POW. We discussed his career options–he had been offered a job handing out the free Metro newspaper, but preferred “making my own hours” as the much-less-lucrative Spare Change vendor. “Plus they check up on you. The manager comes around and makes sure you haven’t just ditched your papers.” Like John, he was intensely interested in and (from what I could see) unwelcomely forthcoming with his compliments for passing women. Frank didn’t like his portrait.

Maria was eating an apple outside the Coop. She was wearing a hoodie and, incongruously, a mink coat. A gentleman with a Duck Dynasty style beard, Indio, was introduced to me as her husband. “You’re her husband?" I asked. “I take care of her,” he said.

Because of the paucity of shelter caused by the closing of the Long Island Shelter, I asked Indio what their plans were for the winter. “Heading down to Raleigh,” he said. Apparently Raleigh, NC has an enlightened attitude towards the homeless. “Maybe out west.”


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