On a recent afternoon near Grand Central Station, Will Colby leaned against the wall at his usual spot on East 42nd Street and fumed about the seasonal encroachment of a class of people he considers fair weather interlopers: summer panhandlers.

“There is already an influx of panhandlers, and people are less sympathetic because it’s summer. In the winter, people are like, damn, you’re cold, you’re out here, you don’t have nobody to help you,” he said in a lilting Alabamian accent.

With a cardboard sign that read “Broke, hungry, God bless” propped near his combat boots, Colby sat alongside his adopted pit bull Zola—which the 32-year-old outfitted in a denim doggy jacket he sewed together.

“There are people out here you compete with who haven’t paid their dues to the street — they only come out during the summer.”

Colby told me he has panhandled off-and-on since 2002. He’s plied his trade in Los Angeles, Portland, and most recently Baltimore, where his application for a Pell Grant fell through and he wasn’t able to attend art school. Colby is also one of the over 250 panhandlers I’ve interviewed as a part of my Word on the Street New York project.

With Zola’s head resting in his lap, Colby, after chatting with several passersby who regularly give him food and a few dollar bills, resumed his critique.

“I don’t like people who have a sense of entitlement. I don’t care whether someone is a war criminal or a philanthropist; for a stranger to give you something, it is an act of kindness,” he said, adding that he’s witnessed many instances in which the seasonal panhandlers in question have been drunk and disorderly, or have refused any donations that aren’t monetary, even food.

“Even if it’s just for the benefit of doing it in front of a friend, or if they’ve once done something harmful, they’re buying back” in terms of karma, Colby explained.

Such a harsh judgment of those who solicit money may seem peculiar coming from a panhandler. Yet to hear Colby tell it, there is a discernible hierarchy to begging: He places the weathered, proud year-rounders, who abide by a code — careerists like him — on top, and the ones he considers questionable or problematic, often known as “traveler kids,” on the bottom.

A couple sleeps on the Bowery in June, 2012 (courtesy Benjamin Curry / Flickr)

While panhandlers interviewed for this article acknowledge the culture clash as their numbers reach a summertime apex, it’s impossible to crunch the numbers of any preexisting panhandler population data: there is none.

Mary Brosnahan, the president and CEO for the non-profit advocacy group Coalition for the Homeless, said panhandler numbers are very difficult to discern, as no agency keeps them.

While Broshnahan says she’s empathetic to panhandlers’ plight, she noted that “Panhandlers and the homeless are not one in the same.” Soliciting money, after all, is an occupation people assume when in crises; homelessness is a living condition.

What the Coalition does track is the Great Depression-rivaling number of people in the city’s shelter system on any given night: In June 2015, the system received 58,761 people each night, including 21,675 adults in families, 23,692 children in families, and 13,394 single adults. This number does not include, of course, the street homeless who forego the notoriously violent homeless shelter system’s front end.

According to the New York City Department of Homeless Services’ 2015 Homeless Outreach Population Estimate (HOPE), there were 3,182 people living in streets, parks, subway stations, and other public spaces.

However, the survey’s methodology garners criticism from homeless advocacy groups. For example, the H.O.P.E. count happens only once a year, which doesn't allow for seasonal ebbs and flows.

What’s more, Brosnahan says, because the survey happens in the dead of winter (January or February), the street homeless, by virtue of survival, go to greater lengths to hide themselves from the elements. As a consequence of bedding down in abandoned buildings or uncompleted construction sites, the street homeless are out of sight of both the public and the approximate 3,000 D.H.S. volunteer surveyors.

Both Sam J. Miller, the communications coordinator at Picture the Homeless, and Brosnahan declined to estimate the street homeless population. As for panhandler numbers, Miller wondered why any agency would track them. Panhandling, after all, is work.

“The city doesn’t keep track of how many editorial assistants or gaffers or freelancers there are — it’s simply no one’s responsibility.” He added that since crises are by their nature transitory, the fluctuating number of panhandlers would be impossible to quantify or predict.

Will Colby in the winter (Peter Madsen / Gothamist)

Aggressive panhandling, which includes obstruction of pedestrian or vehicular flow and intimidation tactics, is illegal anywhere, and is not the same as peaceful panhandling, which is legal.

Perplexingly, the NYC website nonetheless encourages citizens to report panhandling in progress by dialing 911, assuring them that officers will respond when not “handling emergency situations.”

By press time the NYPD had not replied to our request for comment.

Where the city is clear on panhandling is its illegality on subway cars and buses. On March 2nd, 2014, NYPD Commissioner Bill Bratton reported 274 subway arrests for panhandling and peddling that year — that’s a 300% spike from the same time in 2013, according to the New York Daily News.

However, the number conflates panhandlers with unsanctioned buskers, dance performers and teenagers selling candy as a high school fundraiser. NYPD spokesperson Commissioner Stephen Davis told the Daily News the crackdown on “aggressive panhandling” was a result of enforcing “quality of life” crimes, per the commissioner’s devotion to the broken window theory. That’s to say peaceful behavior that is legally protected on the street is criminal in the labyrinthine MTA subway system below.

The dearth of panhandler information means we know very little about New York City’s panhandling economy.

For his part, Colby panhandles seven days a week at his 42nd Street spot, from 3 p.m. to 8 p.m., with the goal of generating $100. That’s a good day. “Flying a sign,” as it’s known on the streets, is just one of the ways Colby cobbles together enough money each month to afford the $600/month rent in a Bushwick apartment he shares with two roommates. He said each month he receives $215 in welfare, a varying amount for odd metal-smith work, and about $300 for the aforementioned punk-styled dog vests, which he sells on consignment for $150 a pop.

Colby is able to preserve money for art supplies and for the grain- and poultry-free food his rescue dog’s sensitive stomach requires. He said he likes working for people, but only if they’re not a “slave-driver,” a corporation, or some other “negative venture." He’s an admitted idealist. Odd jobs he said he enjoys include cutting grass, raking leaves, and painting houses. He said he’d like to start his own company, but the cost of licensure is prohibitive.

Colby counts himself as a panhandler purist and cites his demeanor — pleasant, genuine, and quick to gratitude — as setting himself apart from lesser sign-flyers. Colby spoke disparagingly of a panhandling couple whom, when not assuming the sidewalk spot he’s claimed for years, repel would-be donors by their nearby messy site and unabashed nodding off; the effect, he presumes, of opiates.

It’s this last transgression that Colby — a recovering heroin addict who abides a methadone program — considers unforgivable: The woman in question often flies a sign that says she’s pregnant.

“People see them, then turn the corner and walk by me and think, ‘Nope, I’m not giving anyone any money because they’re all on the street because they’re strung-out.’ It stereotypes anybody who is out here on the streets, especially during the summer — as lazy,” Colby said.

Mary McSweeney (Peter Madsen / Gothamist)

While other panhandlers — past and present — acknowledge the dissonance among camps, not all agree on the labels for each other. Sitting at an outdoor table at the Seward Park library branch on the Lower East Side on a sunny day in May, Mary Catherine McSweeney thoughtfully puffed on an untaxed Double Happiness-brand cigarette she scores for $3 per pack.

The 29-year-old was homeless in Manhattan from April 2009 to January 2015; I interviewed her several times over the course of those years. In 2012 she kicked her heroin habit by switching to methadone; however, she said she filled the massive void left by heroin with alcohol, and became an alcoholic. Now almost nine months sober, McSweeney has since been placed in a transitional living community in NoHo with the help of Goddard Riverside Community Center.

McSweeney quickly acknowledged the culture clash among sign-flyers. Although she’s an acquaintance of Colby and said she’s fond of him, she rejected the “summer-core/winter-core” dichotomy as simplistic. McSweeney said “oogles” (rhymes with Google) is the term often used to describe transient panhandlers who “aren’t strong enough to make it through winter on the street.” She said when she first arrived in the city, more established panhandlers treated her as an oogle; a misclassification from which she graduated as her stay on the streets turned from months into years. It’s this period in her life that McSweeney now spends four hours a day writing about as she pieces together a memoir.

“They look at it as fun and games,” McSweeney said of oogles she has known. “For those of us who do stick it out through the winter, it’s not fun and games; this is our life. They come here in the summer when it’s easy.” She also accuses them of recklessness, indiscreet illegal activity, and wanton drug use in places like Tompkins Square Park and Union Square.

“They’re like, ‘Oh, I’m invincible, this is New York City, no one is going to notice I have a needle sticking out of my arm,” she said, adding that this group “makes a mockery of real sufferings—ones we endure.”

Some panhandlers have reclaimed the term oogle; a self-described squatter founded the Tumblr page called Look at this Fucking Oogle which serves as a popular online communal hub.

McSweeney did admit that some “street kids” — a catchall term for street homeless and panhandlers she said ranges from 17 to 35 — have their hearts in the right place. They’re idealists unapologetically out of sync with the status quo.

“Some are bored with their 9-5’s or school or maybe they don’t see how they’ll have a happy ending in the system, so they’re just going to live their lives to the fullest, come what may, devil may care,” she said. “I’m a little bit like that, too.”

The Delray Beach, Florida, native said she had been holding down rent by working two jobs while preparing for her college placement test when she became disillusioned. Three years after her husband absconded with their two children —now 12 and 9 — she came to New York City. If not for succumbing to the allure of heroin, she said her times on the streets could have been a positive experience.

When she was using and on the streets, McSweeney never flew a sign. Instead, she would walk between 23rd Street and Houston Street on the East Side in concentric circles — this way she wouldn’t become an everyday fixture in any one place and time — politely yet incessantly asking the stream of pedestrians for a few dollars, always mentioning the specific goal of raising $42 to afford a hostel bed.

The strategy worked very well. While shelter was an honest end in the beginning, as she descended into addiction, she said she would spend much of the $200 she earned every day on heroin or alcohol and sleep on the streets alongside her then-boyfriend, who was also addicted.

McSweeney no longer solicits money because she receives a $200 monthly stipend from the city’s cash assistance program, food stamps, and a payment from a methadone program.

“Now I don’t have any need to solicit, beg, lie, cheat, or steal anymore,” she said. Anyway, she added, she could never ask strangers for money without the nerve-numbing affects of alcohol or heroin.

McSweeney said she’d like to attend a community college on her way to someday becoming a counselor or therapist to troubled female youth. She’s also making progress in weaning herself completely off methadone; she’s presently only taking six-milligram doses — a small quantity she’s proud of.

Finding a panhandler who’s only here for the summer is relatively easy; traveling panhandlers often advertise their transience on their cardboard signs.

Hunkered down on 14th Street at Fourth Avenue, kitty-corner to Union Square, Craig Gordon’s pizza-box-sized cardboard sign reads in neat all-capital letters: “Hungry Broke Traveling Folk”; he’s embellished the sign with little dog prints, an acknowledgement to Ziggy, his sleepy Boykin Spaniel, curled on a blanket at his side.

Gordon, who’s black, goes by “Blue Brother,” a nickname his grandmother gave him when he was a child. On an afternoon in late May, while dark clouds billowed high above Union Square, Gordon said that he had been in New York City two for weeks. The 36-year-old, wearing a five-panel cap, a denim vest-jean combo, and Nike Air Max’s, said he left his native New Orleans when his lifelong friends, with whom he operated a heroin ring, began getting murdered.

“Before I got killed too, I left,” he said in a New Orleans drawl. “I didn’t want to be trapped in that one spot thinking, ‘I’m going to die here.’”

Since his departure, Gordon said both his parents have died; he has a brother who lives in Staten Island. Having kicked his heroin habit and traveled since 2008 by illegally hopping on freight trains, Gordon said his favorite states are Colorado, Utah, and Idaho for their spectacular natural beauty. He said he has visited all states except Maine—a feat plausible if not for his dubious claim to have travelled by shrimp boat from Texas to Hawaii.

What is indisputable is his outsider-ness in whichever city he lands, a status that informs most, if not all, his interactions. Gordon said it’s common that a local panhandler will approach him and call dibs on the panhandling spot Gordon has assumed for himself, claiming to have occupied the site for years. How would an out-of-towner be the wiser? Instead of succumbing to a local’s-only pecking order, Gordon assumes a different tack.

“I tell them, ‘That’s not a good thing flying a sign right in the same spot for two years; I feel mad sorry for you, man,’” Gordon said, adding that because of his tact, disputes like these rarely turn violent — and he often retains the spot.

After a territorial dispute in Chicago, where he’d previously resided through the winter, a local panhandler threatened Gordon that he was going to return with a gun. He didn’t return. While such a threat was exceptional, Gordon does acknowledge the general resentment local panhandlers harbor toward those who travel, and offers an explanation: The public is more charitable to travelers than to the locals, whom he calls “home bums.”

“People see us travelers and they think, ‘Oh, he ain’t lying; I ain’t ever seen him before,’” Gordon said. He described an instance in which a stranger told a landmark panhandler to go get a job, and then, in the same moment and within eyesight, gave Gordon money. “That fucked him up for real,” he said.

Gordon said that on his first day in Manhattan, he made $100 in 90 minutes by panhandling by Macy’s department store. He said he was shocked: “I’m finished for the day!”

As it is with such an under-investigated subculture, it is tough to verify such claims. One could sit alongside a panhandler, day-in day-out, yet the presence of a reporter and his voice-recording smart phone and notepad deters donations, both Colby and Gordon said.

Nonetheless, toward the end of the interview, a woman politely interrupted Gordon to explain how she received too many free sparkling waters from work. She handed him several bottles and a net of oranges. Gordon said thank you very much and nodded politely. He said within the month he would travel to Portland, Maine.

“Whenever I decide to quit traveling, I’m going to get a job. For real, man. Get me a job and work—straight up,” he said. “I chose to be like this; yeah man. I chose this life because I wanted to travel.”

Kasey with a variation of his sign (Peter Madsen / Gothamist)

On August 9th and later on August 16th, Will Colby’s spot on 42nd Street, near the CVS at Third Avenue, was vacant. On both occasions, across the street and near the base of the Chrysler Building, 21-year old Kascym, or “Kasey” — who declined to give his last name — said he hadn’t seen Colby any time recently.

Each time I met Kasey, who describes himself as "black-white-Puerto-Rican," he sat on a piece of rolling luggage; this time he was reading a coverless copy of David Foster Wallace’s novel “Broom of the System,” which a passing man insisted he read. More a fan of apocalyptic fantasies, Kasey had nonetheless read the first half. “It’s pretty good.”

In noticing his sign (“Stranded here. Trying to get back to wife and newborn. Need $17 to get home. Anything helps! God bless”) I asked if he and his wife were the couple that Colby had complained about months before, and he nodded. “That’s us,” Kasey said. While he denied keeping a messy site, he did admit that he and his wife would nod out—and yes, while she was pregnant.

As Kasey told me about their situation, the simple picture that Colby had painted of them as sloppy summertime interlopers on a lark quickly dissipated.

In February the expecting couple traveled the 95 miles down the Hudson River from their native Kingston to Manhattan because Kasey said there was a six-month waiting period at area methadone clinics. (A spokesperson at the Kingston Hospital Methadone Maintenance who answered the phone acknowledged that there is a waiting period and that it usually lasts “months and months.”) Additionally compounding their problems was the fact that Kasey’s parents had kicked them out of their home when they learned of the pregnancy.

Kasey said his wife, upon learning she was expecting, wanted to quit heroin cold turkey, yet a consulting doctor told them that her doing so could trigger a miscarriage; she was better off using until she could secure a methadone prescription. Kasey said the couple had panhandled and slept on Manhattan streets for several months when they learned the city’s clinics offer day-of treatment — no waiting period. They switched heroin for methadone a week before the baby was born on May 28th.

Their son was born on schedule and suffered no withdrawal symptoms, Kasey said. Since then, the New York City Administration for Child Services placed the baby in a Bronx foster home due to the couple’s living situation. The mother is presently incarcerated upstate for a parole violation; Kasey declined to say what she had initially been charged with. He said they speak daily on the phone. They don’t know when she will get out.

Although the donations trickle in more slowly during the summer, Kasey said he averages $100 per day — sometimes he makes money while he sleeps at night. He springs for an $80 hotel room in the Bronx a couple nights a week. He also visits his infant son twice a week at a Bronx foster care center.

While his sign gives people the impression that he is destined for the next train out of Grand Central Station — he said he’s been called out for it by a regular commuter — Kasey said his sign is more of a reflection of his long-term goal of reuniting with his wife and son; he doesn’t intend to spend another winter on the streets. Social workers from the Coalition for the Homeless and another agency are helping him make the necessary steps — which includes staying sober, taking some parenting classes, and regaining housing — so he can earn custody of his son.

“I’m saving money and I’m working my way to getting a job again.” Kasey said. “I want to start my life over.”

Peter Madsen is a freelance reporter and the author of Dealers. He lives in Williamsburg, Brooklyn.