In May 1923, a determined seventeen-year-old boy stared out from a page of The Brooklyn Daily Eagle. Above his thick blond hair ran the headline helps build queens. Two paragraphs announced to the world that this teenager, Fred C. Trump, envisioned “a big future in the building industry.” He would become a “builder,” he declared.

The borough of Queens was exploding with growth all around him. The population had roughly tripled since his birth and would double again by 1930. His alma mater—Richmond Hill High School—had been built for eight hundred students but was already jammed with two thousand teenagers. Classes were held on the front steps. Students waited in line for a desk in the study hall.

Outside, the streets teamed with new arrivals, mostly from Germany and Russia. The demand for housing was unyielding. It was a time when a paved street and a sewer line were luxuries notable enough to mention in an advertisement. Former farms and forests in Queens offered vast stretches of open land, newly within reach of Manhattan. After the Queensboro Bridge had connected the boroughs in 1909, train lines and trollies pushed farther and farther out. Real estate developers rushed to the site of each new train stop and advertised homes to Manhattan-bound commuters: “5-cent fare zone!”

Amid this epic building boom, Fred Trump worked incessantly to find his place. He ignored his school’s extracurricular activities—the sports teams, the acting and singing troupes, the chapter of Arista, an honor society. Instead, he worked, earning money and learning how to build homes. He delivered building supplies to construction sites with a horse-drawn wagon. He took a job as an assistant foreman with a construction company. He eventually built a garage for a neighbor. He would come to believe that even his choice of childhood toys—blocks and erector sets—foretold his destiny.

In some measure, his interest in real estate tracked the unfulfilled dreams of his late father. His parents, Frederick and Elizabeth, had arrived from Germany during an earlier immigration wave, in the late 1800s. Frederick traveled to the western frontier, where he ran a restaurant that had once also operated as a brothel. He returned to New York City to manage a restaurant and pursue small real estate investments. He bought his young family a simple two- tory house on a dirt road in the Woodhaven section of Queens, one block south of the bustling Jamaica Plank Road, then a key route packed with horse- drawn carriages making the journey to Manhattan from the farms of Long Island. Their neighbors mostly rented their homes and worked as janitors, house painters, store clerks, and in the shipyard.

Frederick’s real estate career had just begun to gain momentum when he was struck down by the Spanish flu, the pandemic then ravaging the world. He died in 1918 at the age of forty- nine, leaving Elizabeth alone to raise their three children: Fred, twelve, John, ten, and Elizabeth, fourteen. They would not be destitute. Frederick left his wife an estate valued at $36,000, the equivalent of more than $800,000 today, mostly in the form of money due on loans he had made to builders and the value of a few vacant lots.

Elizabeth assumed the role of the family’s business leader. While Fred was still in high school, his mother hired contractors and oversaw the building of homes on the vacant lots she owned. She had designs on creating a family real estate company with her three children. John, who had a way with figures and details, would become the architect. Elizabeth, her oldest, would run the office. And Fred would become the builder. She formed the first Trump family enterprise, E. Trump & Son, artfully masking her own gender and her two sons’ youth.

Fred threw himself into the role. He took classes at a local YMCA in carpentry, and more classes to understand blueprints and engineering. He and his mother began buying undeveloped land. They did not borrow money to build. They would pay cash for a lot or two, Fred would work frantically to build a house, and they would offer it for sale before he had finished in hopes of using the proceeds to buy another piece of land. By the time Fred was in his early twenties, he and his mother regularly placed classified advertisements to sell homes under the E. Trump & Son name, offering easy terms for buyers.

By 1925, Elizabeth and her children moved a little farther out, to the neighborhood known as Jamaica, a name thought to be derived from the Native Americans known as Jameco, or Yamecah, who once lived there. The Trumps bought a house south of Hillside Avenue, the dividing line between the modest homes and tight lots of Jamaica to the south and a new world of wealth to the north, christened Jamaica Estates.

Jamaica Estates had been founded by an early generation of New York real estate royalty, nineteenth- century men with cookie- duster mustaches and formidable bearings. The best known of them was Felix Isman, considered to be worth $30 million in his early thirties and famous for having said a man could be correct about New York real estate only three quarters of the time and still make money.

Another Jamaica Estates founder, Michael J. Degnon, had been instrumental in construction of the Williamsburg Bridge over the East River, much of the new subway system under Manhattan, and a massive industrial park in Queens. Degnon himself bought the most prime swath of land in the area, a sixteen- acre plot atop the hill rising behind the owner’s lodge. He commissioned a stone mansion surrounded by streams and forest. Newspapers articles of the time claimed that the highest ground in Jamaica Estates offered views of the Atlantic Ocean to the south and Long Island Sound to the north.

Isman, Degnon, and the other founders had modeled Jamaica Estates after an exclusive gated community in Orange County, north of New York City, known as Tuxedo Park. The black suits and ties with crisp, white shirts favored by the men of the community came to be known as tuxedos. Jamaica Estates would not have a gate, but it would have a stone gatehouse where Midland Parkway, conceived as the most exclusive address in the community, began its path north from Hillside Avenue. To the right of the entrance, the founders constructed a large Elizabethan- style lodge. They hired a famous landscape architect to incorporate the parklike qualities of the area into the street design, with roadways gently arcing around mature trees and hills. The founders gave streets names that evoked English estates— Cambridge, Devonshire, and Wexford Terrace. There would be tennis courts near the entrance, and a golf course on another neighborhood border.

For all their experience, the founders’ vision to create an enclave of extreme wealth did not hold. The original partnership dissolved in discord. The neighborhood would remain a pocket of greater wealth than the working- class Jamaica all around it, but one of the mere professional classes. In one long weekend, two thousand lots in Jamaica Estates were sold off by Joseph P. Day, a famous real estate auctioneer of the early twentieth century. Weeks of advertisements and articles in the city’s newspapers created a frenzy. More than fourteen hundred potential bidders showed up to sit under a large tent across Midland Parkway from the owner’s lodge and buy multiple lots. If Fred and Elizabeth did not attend, they most certainly were aware of the spectacle.

From the bedroom where Fred Trump slept in his early twenties, he could walk three minutes north to Hillside Avenue and gaze up at the Degnon mansion, the estate of the legendary builder. He aimed his life toward earning a place in Jamaica Estates alongside the Ismans and Degnons of the world.

A year after he and his mother began regularly selling the homes he had built, they placed an advertisement in The Chat, a Brooklyn newspaper, that read “Builder will sell his own home,” offering their six- room house just below Hillside Avenue for $9,250. Fred built them a house a few blocks north on Devonshire Road. He was not yet thirty years old. For the rest of his life, he would call Jamaica Estates his home.

Only Fred continued in the line of work about which his father had dreamed for himself and his mother had imagined for her children. His siblings went in different directions. John headed to college at the Polytechnic Institute, where he would be class valedictorian, and then to earn a doctorate from the Massachusetts Institute of Technology, where he became a respected professor and researcher. Their sister, Elizabeth, married a banker named William Walter, and they moved into one of Fred’s early homes.

After several years of building modest houses in other neighborhoods, Fred set his sights on the wealthier buyers in Jamaica Estates. He built sixteen homes along both sides of Wareham Road, the next street over from the premiere addresses along Midland Parkway. Unlike his prior focus on utilitarian simplicity, these homes would feature architectural details and modern amenities. Most would be Tudor revivals, with multiple gabled rooflines and a mix of stone, brick, and wood- trimmed stucco. They featured landscaped yards and two- car garages. Then twenty- five years old, Fred spoke with a reporter about his experiences with discerning buyers during “my ten years in the building and developing field.” He listed the homes at prices ranging from $17,500 to $30,000, multiples of anything he had built before.

“Stroll around this parklike section,” urged his advertisement in The Brooklyn Daily Eagle. “You will wonder that this community, so like the aristocratic estates of Old England, is within the limits of New York, and but twenty minutes from Broadway.

“No detail has been spared that these homes might suit the individuality of the high type residents in this community.”

At the bottom of the advertisement, there was no reference to his mother. Only one name appeared, offset by the job title that might have seemed like a distant dream just a few years earlier: “FRED C. TRUMP, Builder.”

Fred Trump remade himself as a builder for the “high types” just as the national economy collapsed into the worst depression in the nation’s history. Hundreds of thousands of properties were lost to foreclosure. Newspapers featured long lines of recently unemployed men waiting for food handouts. Nearly one quarter of Americans were out of work, with the construction industry particularly hard hit. Roughly half of all construction jobs had disappeared as home building slowed to a crawl.

As the economy hit its nadir, Fred returned to Woodhaven. He built a one- story box of a building near the house where he had grown up. He hung a sign outside— trump markets— and tried his hand at a new type of business, the supermarket, a reimagining of the grocery store with everything the modern homemaker needed under one roof, saving her separate trips to the butcher, the fishmonger, and the fruit stand. It was a concept created by a neighbor in Jamaica Estates, Michael J. Cullen, who had opened what was thought to be the first supermarket, King Kullen, several years earlier. After proudly advocating his aristocratic estates, Fred now peddled “genuine spring legs of lamb” for seventeen cents a pound, along with Chesterfield cigarettes, crab meat, cleaning supplies, dog food, and house paint.

Fred Trump, the grocer, would be a brief diversion. Months after he opened the market, an opportunity arose from the economic devastation. A decades- old financial house, J. Lehrenkrauss Corporation, crumbled in scandal. Fred bid in bankruptcy court for its mortgage- servicing business, eventually partnering with another bidder, a man named William Demm, to win the portfolio of failing mortgages and properties facing foreclosure. During the process, he became impressed with Demm’s lawyer, William Hyman, an athletic- looking, blue- eyed son of Jewish immigrants from Europe. Fred soon parted ways with Demm, but he and Hyman formed a long- standing bond.

Nominally back in real estate, Fred sold his supermarket to Cullen and swore to himself he would never put his name on a business again. He focused his energies on selling the properties in the Lehrenkrauss portfolio. Cleaning up the mess in a failed lender’s real estate portfolio, while a substantial endeavor for a young man finding his way through a horrible economy, was not how Fred had envisioned his career unfolding. But his fortunes were about to take a dramatic turn thanks to the federal government’s efforts to deal with the economic calamity.