The high ceiling lofts feel more SoHo than Lower East Side, though the view of Seward Park High School to the north and tenement bricks from the terraces facing south easily reorient you. This freshly painted blue building gracing Grand Street between Essex and Ludlow Streets originally housed a piano showroom and warehouse before the Sunray Yarn factory took it over, and now it has been reborn as a luxury co-op with million dollar apartments awaiting tenants.

On a recent sunny Sunday afternoon, just as I was passing its doorway, I ran into Michael Lewis, a true-blue, life-long Lower East Side guy—a rare breed nowadays. Lewis, a middle-aged man with his hair tied in a ponytail under a baseball cap, was carrying a basketball; he had been shooting hoops at the refurbished Seward Park basketball courts nearby, now frequented mostly by Asian teens. I know Lewis through the Lower East Side family business connection. The Lower East Side used to be a like a small town—everyone knew each other. For generations, our families had stores a block apart, and now we’ve both made our homes in the neighborhood not too far from the blue building.

The Lewis family operated a ladies clothing store in a building on Orchard Street just south of Grand; mine ran a dry goods shop on the corner of Orchard and Grand. In the mid-90s Lewis phased out his family’s store converting the upstairs’ warehouse into upscale rentals and the storefront into a gallery displaying his mirror-shard sculptures. Lewis made the transition from old-world Lower East Side merchant to new-world Lower East Side real estate entrepreneur as the neighborhood fabric changed from a wholesale/retail center to an artist’s haven. When the area started showing signs of becoming the next SoHo, there were few signs indicating that business would pick up. So, in 1998, my family quietly closed its shop doors. Every time I pass the decorating store in its place it feels strange and sad.

My great-great-grandfather Harris went from being a pushcart peddler to a wholesale/retail storeowner when he opened H. Eckstein and Sons in 1916. My great-grandfather Meyer and his brothers ran it until my grandfather David and his brothers took over the family business after they returned from the service during WWII. (My mother and brother worked there up to its final days.) Eckstein’s sold women’s, men’s and children’s clothing, as well as linens and undergarments. Mounds of jeans were piled in the basement, and since the store had no dressing rooms, people would try things on behind stacks of Wranglers and Levi’s. Shelves of brown cardboard boxes stuffed with underwear lined the walls; to get a pair, a salesperson would climb wooden ladders precariously affixed to a bar just below the tin ceiling. I remember spending Sundays there as a kid—I once scored an imitation snakeskin wallet I found stashed between the Dr. Denton pajamas (with “feet”). It was usually so crowded that the only person who could see and talk to me was Ben, the short man who worked in the sheets department, whom everyone referred to as “the midget.”

Eckstein’s was one of the hundreds of Jewish family-owned and operated businesses in the Lower East Side. These stores sold goods for cheap and customers would pay even less if they knew how to play the haggling game. If a sweater’s price tag was marked $15, a customer might offer $10 to open up negotiations. The salesperson might then respond, “Two for $24.” At Eckstein’s, all of the workers knew a ten-letter code word, each letter corresponding to a digit, so they could shout out prices to charge customers. No two customers paid the same price for an identical purchase, but customers almost always received a discount. In the end, the customer felt triumphant for having knocked the price down, and the store made another sale. Though the Lower East Side Business Improvement District tote bags continue to label the area as “the bargain district,” today’s newly opened boutiques rarely understand, or have any patience for, this lost art of haggling.

Storeowners’ games extended beyond customers; they played with the law, too. The Jewish-owned shops closed Friday afternoons through Saturday in observance of the Sabbath, but would then open on Sunday, flouting New York’s Blue Laws – which meant that everyone spent Sundays shopping on the Lower East Side. Storeowners received a nominal fine each year for violating the laws, and basically the city would look the other way, letting these stores continue their Sunday business. (Also, to bring in more business in the lean ‘20s and ‘30s, shop owners would open on Saturday nights.)

Nowadays there are still stores with their gates rolled down on Saturdays; some are Jewish-run stores and others are simply empty storefronts that are permanently gated. There’s a vacant corner on the blue building’s block, which used to house the Grand Dairy, a favorite kosher lunchtime hangout (serving only dairy, no meat). The Grand Dairy opened right after WWII ended and, according to my grandfather, was the first restaurant in the area with air conditioning. A heat wave seduced the Jewish merchants and “jobbers” (wholesale middlemen) away from the Mayfair, another popular Grand Street restaurant. The Mayfair, which had held on through the Great Depression on the corner at Allen Street, underneath the shadows of the elevated train tracks, couldn’t compete with air conditioning and soon closed its doors.

Disappointed Mayfair customers like my grandfather and his brother Herbert quickly became Grand Dairy regulars. Herbert had a special sandwich at the Grand Dairy named after him called “the professor”—an open-face tuna sandwich with a salad. Herbert was a scholar of salesmanship. He stood up front next to the manual cash register (Eckstein’s never went digital; cash or check only), and he would not let customers leave the store without making a purchase. They also couldn’t escape without revealing their marital status. For single customers, Herbert had a match.

The Grand Dairy stopped serving its lunches in the early 1990s. By then, many of its Jewish merchant clientele had already left. Nowadays, the lingering Lower East Side family businesses have turned into nostalgia shops for Sunday tour groups lured to the area by the Lower East Side Tenement Museum, not by shopping. Of the handful of remaining shops, most sell undergarments or hosiery like one on the corner of Grand and Ludlow featuring a window display of faded Danskin tights unchanged in five years. On sunny days, when there’s little business on the street (which is often), I’ve spotted the proprietor sitting in a lawn chair on the sidewalk with one of those aluminum reflecting tanning boards.

As the old-time stores disappear from the neighborhood, the slow but steady development of Lower East Side gentrification rubs shoulders with Chinatown’s expansion, mostly newcomers from Fujian Province. Of course, some remnants of the old Jewish enclave persist. Kossar’s bialy shop continues to produce chewy, bagel-like rolls around the clock, and there are still other kosher food shops on Grand Street. But then there’s also the Donut Plant, a gourmet donut shop with massive donuts, and a no-frills noodle house. I once heard that Starbucks had been interested in the former home of the Grand Dairy, but that the owner had turned them down, not in protest of the corporation’s power, but because he thought he could get more money than the coffee giant was willing to offer.

Michael Lewis may have had the right idea catching the wave of gentrification before it hit its crest, trying to capitalize on the neighborhood’s increasingly fashionable flavor. The streets are no longer, and will never be, the frenetic marketplace jam-packed with shouting peddlers and bickering customers. The Lower East Side dry goods business suffered many blows, such as when the blue laws were revoked and shops all over town opened on Sundays, or when construction on the Williamsburg Bridge during the late 1980s deflected traffic from the area, or when chain stores like The Gap started springing up all over town offering a wide selection of inexpensive jeans.

Perhaps business had really begun declining as far back as the 1930s. I was recently watching It Happened One Night, a depression-era movie starring Clark Gable as a fast-talking newspaperman who wins the heart of Claudette Colbert, a tycoon’s daughter. There is a scene in which Gable takes off his button-down shirt revealing a bare chest, no undershirt. My grandfather always said that one scene single-handedly destroyed the undershirt business. And not even Marlon Brando could reverse the trend.