Laura Eisenberg—Getty Images
By Jacob Davidson
October 7, 2014

It’s a story right out of a Ronald Reagan campaign speech: Oklahoma City resident Brandi Newman saw an elderly woman asking for money to buy food and generously handed over some cash — only to spot the same woman a few minutes later behind the wheel of what appeared to be a brand new, candy-apple-red Fiat.

Newman says she felt scammed, and she wasn’t the only one. A viral video subsequently recorded by Newman — in which another angry benefactor berates the 78-year-old widow for taking his donations under false pretenses — has been viewed more than 3 million times on Facebook and YouTube.

“You’re asking for money in the middle of the street, and you’re driving a 2013 car?” screams Daniel Ayala. “Listen, I work hard for my money, I don’t appreciate this sh*t!”

Why was this man so angry over what is, after all, just a few dollars? And why has this video seemingly touched a nerve?

For many of us, of course, it’s impossible not to feel compassion for the legions of homeless and hungry who ask us for spare change. And yet, in the back of our minds, this compassion comes packaged with a gnawing suspicion: Is that person really needy? Is my money being wasted? Am I being scammed?

The crooked beggar is a deep and long-standing societal fear: a squanderer of limited resources; a cynical manipulator of our noble instincts; the embodiment of what economists call “moral hazard.” And this bogeyman has at least some basis in reality. Reagan’s famous story during the 1976 presidential primaries about the Cadillac-driving “welfare queen” has been dismissed as an exaggeration, but as Slate‘s Josh Levin has explained, she was actually quite real. More recently, a 45-year-old self-described “lazy” man named Warren Speegle (also, as it happens, in Oklahoma City) reportedly told arresting police that he was able to make $60,000 a year panhandling and consequently saw no reason to try to get a regular job.

On the other hand, at least one recent study of San Francisco’s homeless suggests that these notorious cases are aberrations. The majority of the city’s panhandlers, it found, gather less than $25 a day and 94% use the money they receive for food. (The research also confirmed some less favorable assumptions. For example, 44% used donations on drugs and alcohol.)

Newman’s video, in short, seems to crystallize the moral complexities we face each time we are confronted by someone asking for money on the street.

It also forces us to ask a number of uncomfortable questions: Are we right to care about how our charity is spent? Is our skepticism justified? And, most importantly, how do we get help to the people who need it most? So we decided to put them to some experts.

The community organizer: “Not all homeless people are scammers.”

Michael Stoops, director of community organizing at the National Coalition for the Homeless, urges people not to assume every panhandler they encounter is a scam artist. When told about the incident in Oklahoma City, he points out that every group has a few bad apples. “If you send me $5, unless you told me you wanted to buy a meal for someone, I could buy a box of jumbo paper clips [instead]” says Stoops. “Sometimes it’s okay to give to the middle man, but not all homeless people are scammers and not all scammers are homeless. There are also scammers in Congress and in the business world.”

Stoops acknowledges that we have reason to be concerned about how our cash is spent once it leaves our hands. But he argues that people who ask for money on the street deserve the same trust we would afford to anyone else. “Do you really have the right to follow someone to the liquor store?” he asks. “The answer is no.” And just because a panhandler has a car, or even a comfortable place to live, doesn’t mean they don’t need help. (Leslie Lenkowsky, a professor of Philanthropy at Indiana University, even told MONEY about one program that provides cars to low-income women to help them travel to work.) “If you could make a lot of money panhandling, I might be out there on the street myself,” Stoops adds dryly.

The civil rights lawyer: “People may present a false image of their plight.”

Mark Weinberg, a Chicago civil rights lawyer who has spent more than a decade defending the rights of panhandlers, understands where our suspicions come from. “It’s an exploitation of people’s empathy,” says Weinberg of the video. “I think that actually goes on in the world of panhandling. People may present a false image of their plight.”

“I don’t think any of these people are rich,” he continues, but his experience can make him skeptical. “I’ve seen all different situations of the past 12 years, and one of the confusing things is it’s hard to tell who’s in that situation of desperation where you truly do want to help, and who’s using the money to pay for their cable TV.”

The fundraiser: “There’s only so much we can do for someone as an individual.”

James Winans works to provide for the needy on a daily basis as the head of development at New York’s Bowery Mission. He says he would never try dissuade anyone from giving money directly to someone on the street. “We all have to do what we think is right,” Winans says.

“But what I do say to people is, first, there’s only so much we can do for someone as an individual; and second, there’s only so much we can know about another person’s situation.” For those worried about their money being misused, the Bowery Mission offers business card-sized printouts on its website listing the organization’s location and range of services. The cards can be given instead of cash, or with money wrapped inside. Says Winsan: “It’s great to connect that person with a community that can help them.”

The Bowery Mission offers resource cards to be given with, or in place of money.

The homeless advocate: “Giving money to people on the street is not going to solve the problem.”

Steve Berg, vice president of the National Alliance to End Homelessness, agrees that giving to an individual isn’t a bad thing, but also won’t really fix anything. “It might make life a little easier,” he said in a phone interview, “but it’s not going to solve their homelessness and it’s not going to solve the whole community’s problem with homelessness.”

Instead, Berg urges concerned citizens to support anti-homelessness policies that have been proven to work. Thanks to a $300 million federal program to solve both short- and long-term homelessness among veterans, the number of former service members on the street has decreased from 76,000 in 2010 to fewer than 50,000 in January of 2013—a drop of over 35%. The Obama administration has proposed another $300 million to end chronic homelessness by 2016, and Berg is optimistic that another bipartisan coalition will approve those funds as well. In addition to supporting more federal efforts, he suggests peoples ask their mayor’s office which local organizations need assistance.

For those who want to help a specific person they meet on the street, but want to avoid being misled, all four experts interviewed suggested a simple method: Ask the person what they need and why. “To find out what someone needs takes time and that’s a higher level of sacrifice,” Winans says. “But I think it’s actually more effective. If people are willing to put themselves out there to panhandle, they’re usually willing to tell you about why they’re doing it.”

We also reached out to Charity Navigator for help finding some of the best organizations that work to fight poverty and homelessness. Some charities to consider (in addition to all those mentioned in this article) are The Robin Hood Foundation (which operates in New York City), Feeding America, Habitat for Humanity, LIFT, and the Boys & Girls Clubs of America.

Correction: This article previous stated Leslie Lenkowsky was a professor at the University of Illinois. He is actually a professor at Indiana University.

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