Inexplicably, the man on line ahead of my girlfriend at our local Walgreen’s pharmacy was returning two small packs of Juicy Fruit gum, each with a separate receipt. He was dressed in that combination of Carhartt hoodie and baggy jeans that feels both hip hop and rural, young, skinny, white, and somehow a little bit off—voice too loud, slightly too confrontational.

“A junkie?” I asked when she told me the story, since her description squared with the modest assemblage of heroin addicts who routinely straggle intermittently among the methadone clinic downtown and the shelters, churches, food pantries, and drug spots around our neighborhood.

“He was definitely on something.”

The cashier huffed in annoyance when the young man presented the gum and receipts. He asked, “Is that gonna be a problem? Because I asked the manager,” and here, he gestured toward the back of the store, “and he said it wouldn’t be a problem.” He seemed like he was spoiling for an argument. The cashier shrugged, took the gum and receipts, and gave the man his modest refund.

After he was gone, my girlfriend asked the cashier what it was all about. She explained that it was a frequent occurrence, and somehow involved buying gum with an EBT card at one Walgreen’s and then returning it at another, effectively converting government food assistance into cash, albeit in tiny increments. Just then, the manager came by and the cashier asked whether he had authorized the gum refunds. He had not.

As hustles go, the gum refund scheme strikes me as way more trouble than it’s worth: walking from drugstore to drugstore for a 70-cent payoff seems like a poor return on investment, and most street drugs these days can’t be bought in quantities small enough to cost less than at least five dollars. But perhaps the gum racket was but one of many small-time hustles that our protagonist was working simultaneously as he wandered around Hartford.

There is certainly no shortage of other hustles: a couple weeks ago, a well-dressed man pitched me a story in Dunkin Donuts about having lost his wallet and run out of gas, needing to get to Bridgeport, etc., etc. The next day, apparently not recognizing me, he tried again a few blocks away. “You sold me that bill of goods yesterday!” I said, and he just walked away cursing. At least once every summer, when I’m sitting outside at the neighborhood bar down the block from my building, someone tries to run the out-of-gas hustle with an actual jerry can. I appreciate the extra investment in veracity, but I don’t offer money.

When I was a kid, there were known places around my mom’s neighborhood in Brooklyn where food stamps—which were actual pieces of paper then and not a debit-style card—could be used for non-food purchases, or traded for cash, with the merchant taking a percentage of face value for the risk and trouble. That didn’t strike me as a hustle, exactly—it was just something people did, and I didn’t even understand it to be illegal until much later. Nevertheless, I have always appreciated the little hustles and hook-ups that get people from paycheck to paycheck.

Brooklyn in that era (the pre-hipster, pre-Giuliani era) was in a golden age of small-time hustles. Around July Fourth, old guys from Chinatown would come around selling illegal fireworks to kids on the block. Then some teenagers from the next building went somewhere (Jersey? Staten Island?), bought fireworks in bulk, and drove the Chinese guys off with lower prices. The ice cream truck on our block sold ice cream and weed and harder stuff too. All the bodegas sold loosies (single cigarettes) for a quarter; most sold beer to teenagers; a few sold pre-rolled joints from behind the counter. When I was a teenager, I met some guys from Trinidad who made rum in their basement. Good rum.

My mom was the hustle champ. She would always bake bread or mend clothes for people, usually in exchange for a dime bag or some choice cut of meat, probably nicked from someone’s hotel or restaurant job. In our building, people knew she had beautiful handwriting and would sometimes hire her to address invitations or write notes in greeting cards. She had a knack for finding slightly used things in the trash—shoes, appliances, furniture—and storing them away to spruce up and barter at a later date.

My hustle game was tightest when I was in college. I dated a girl who worked at a gourmet grocery store in TriBeCa who would feign scan all my food before charging me for only the bottle of Snapple that I’d put last on the belt. By the time she left that job, I’d befriended enough of her coworkers that I kept getting free groceries for the next year, and they would tip me off when slightly past-their-prime veggies were getting tossed, and hold them for me at the back of the store.

Around the same time, I worked for Pepe Jeans in their Latin American distribution office, which is actually a real thing. There was a showroom full of clothes from two seasons ahead, and every week or so, one of the handful of businessmen with contracts to manufacture and distribute Pepe Jeans for various Latin American markets would show up to be pampered by us and watch models show off the overpriced streetwear that the elites of Paraguay and Panama would be wearing in six months. The businessmen, perennially tipsy and invariably sketchy (the one from Panama was always accompanied by two new “assistants,” thin, blonde twenty-somethings who appeared to be working a whole other level of hustle), would choose the styles they wanted to manufacture and negotiate the licenses, after they were gone, through a series of faxed letters.

My job was mostly to translate correspondence from the businessmen, answer phones, and run errands, for which I got $9 an hour and a flexible, college-friendly schedule. Then one day, while waiting on some printing job at a copy shop in midtown, I got to shooting the shit with a guy who worked there, a heavyset dude from Brooklyn. “Yo, they got clothing samples where you work?”

“A ton,” I said. “Pepe and Hilfiger.”

“Y’all get to carry them home for yourselves?”

“Sometimes,” I said, and I started to smell business. “They all got a little rip somewhere in them, so when they ship them in from China, we can tell customs they’re not worth anything. Some of them you can’t even find the rip, so those are good, but some got a big slash down the back.”

“But y’all could just carry them whenever?” He was very interested.

“Nah,” I said. “They let us take a few each season, and then maybe we could slide with a few more, but any more that that and I could lose my job.” That was a lie. After all the distributors had made their seasonal visits, the samples just sat in unlocked cabinets until they were cleared out and shredded to make room for the next batch. Employees could take them with impunity.

“Listen,” says the copy shop guy, boxing up my documents. “If you found some Hilfiger jeans with a 40-inch waist that you could carry, and they were from the next season, like not on the street yet, feel me? A hundred bucks.”

“What days you work?” I asked, and thus commenced the best hustle of my young life. That extra $200 a month when I was working and in school allowed me to start building up a modest savings that would prove essential during my lean AmeriCorps year, and again later, when my dad couldn’t afford a suit to wear to my wedding.

In law school, I worked as a house mover, which is really just a job and not a hustle, but my partner in this endeavor had taken hustle to the next level. He was pretty much running game at all hours.

Through bribes and charisma, he had developed relationships with the employees of all the UHaul locations around Boston. This proved crucial on Boston’s big college move-in and move-out weekends. Every UHaul from Providence to Portsmouth would be booked solid, but we could get a job on Friday and pick up a truck Saturday morning. We made a lot of money on those weekends.

My partner would also sometimes do long haul moves. He noticed that round trip truck rentals charged by the mile, but one-ways were priced according to the distance between pick-up and drop-off. So for a run to Raleigh, North Carolina, he booked a truck from Boston to Worcester, drove to Raleigh and back, and had me scoop him up a half hour west of Boston. He made an absurd amount of money from those gigs, and usually came back with fancy appliances and leather couches that people had decided at the last minute not to keep in their new homes. Naturally, my partner knew where to sell those things.

He also used to park his decrepit VW bus on the street near Fenway the morning before a Red Sox game. An hour before game time, he would stand on Longwood Avenue with a cardboard sign offering parking for $2 less than what the lots were charging. He’d lead the first taker to his bus, give up the spot, and drive off to some neighborhood where parking was less coveted. It may not have been the most efficient way to make $15, but it beat chewing gum refunds.

And you, dear readers? What are some hustles and hook-ups that you have seen? What are the ones that you use to get by?

You probably thought I’d let you listen to Jay Z’s “Can’t Knock the Hustle” while sharing your hustle stories in the comments, but that’s just too predictable, plus you’ve definitely heard it before (ditto for “I Just Wanna Love U,” even though Pharell singing “I’m a hustler, baby” on the hook is kind of perfect). Instead, check out “Ice Cream Man,” about an ice cream truck hustle much like the one I remember from my youth. It’s a really solid summer anthem, and it’s by a Hartford rapper (we have some!).


Josh Michtom is a public defender in Hartford, Connecticut. He spends way too much of his spare time decorating his children’s school lunch bags.

Photo: Davidd


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