In September 1908, the family moved to Woodhaven, Queens. At the age of 10, Fred worked as a delivery boy for a butcher. About two years later, his father died in the 1918 flu pandemic. From 1918 to 1923, Fred attended Richmond Hill High School in Queens, while working as a caddy, curb whitewasher, and delivery boy. Meanwhile, his mother continued the real estate business Frederick had begun. Interested in becoming a builder, Fred took night classes in carpentry and reading blueprints. He also studied plumbing, masonry, and electrical wiring via correspondence courses.

After graduating in January 1923, Trump obtained full-time work pulling lumber to construction sites. He found work as a carpenter’s assistant and continued his education at Pratt Institute. Trump’s mother loaned him $800 to build his first house construction project, which he completed in 1924. Elizabeth Trump held the business in her name because Fred had not reached the age of majority. “E. Trump & Son” was established in 1925 and did business as early as 1926. That year, Trump built 20 homes in Queens, selling some houses before they were complete to finance others. The company was incorporated in 1927.

On Memorial Day in 1927, over a thousand Ku Klux Klan members marched in a Queens parade to protest “Native-born Protestant Americans” being “assaulted by Roman Catholic police of New York City.” The 21-year old Trump and six other men were arrested. All seven were referred to as “berobed marchers” in the Long Island Daily Press; Trump, detained “on a charge of refusing to disperse from a parade when ordered to do so,” was dismissed. Another of the men, arrested on the same charge, was a bystander who had had his foot run over by a police car. According to the police, the five remaining men were certainly Klan members. Multiple newspaper articles on the incident list Trump’s address (in Jamaica, Queens), which he is recorded as sharing with his mother in the 1930 census and a 1936 wedding announcement. In September 2015, Boing Boing reproduced the article, and Fred’s son Donald Trump, then a candidate for president of the United States, told The New York Times, “that’s where my grandmother lived and my father, early on.” Then, when asked about the 1927 story, he denied that his father had ever lived at that address, and said the arrest “never happened,” and, “There was nobody charged.”

In 1933 Trump built one of New York City’s first modern supermarkets, called Trump Market, in Woodhaven, Queens. It was modeled on Long Island’s King Kullen, a self-service supermarket chain. Trump’s store advertised “Serve Yourself and Save!” and quickly became popular. After six months, Trump sold it to King Kullen.

In 1934, Trump and a partner acquired in federal court the mortgage-servicing subsidiary of Brooklyn’s J. Lehrenkrauss Corporation, which had gone bankrupt and subsequently been broken up. This gave Trump access to the titles of many properties nearing foreclosure, which he bought at low cost and sold at a profit. This and similar real estate ventures quickly thrust him into the limelight as one of New York City’s most successful businessmen.

Trump made use of loan subsidies created by the Federal Housing Administration (FHA) not long after the program was initiated by President Franklin D. Roosevelt in 1934. By 1936, Trump had 400 workers digging foundations for houses that would be sold at prices ranging from $3,000 to $6,250. Trump used his father’s tactic of listing properties at prices like $3,999.99. In the late 1930s, he used a yacht called the Trump Show Boat to advertise his business off the shore of Coney Island. It played patriotic music and floated out swordfish-shaped balloons which could be redeemed for $25 or $250 towards one of his properties. In 1938, the Brooklyn Daily Eagle referred to Trump as the “Henry Ford of the home-building industry.”

Trump met his future wife Mary Anne MacLeod, an immigrant from Tong, Lewis, Scotland, at a dance party in the early to mid-1930s. Trump told his mother the same evening that he had met his future wife. Trump, a Lutheran, married Mary, a Presbyterian, on January 11, 1936, at the Madison Avenue Presbyterian Church with George Arthur Buttrick officiating. A wedding reception was held at the Carlyle Hotel in Manhattan, and they had a single-night honeymoon in Atlantic City. The couple settled in Jamaica, Queens, and had five children: Maryanne Trump Barry (born 1937; a federal judge until her retirement), Fred Trump Jr. (1938–1981), Elizabeth Trump Grau (born 1942), Donald Trump (born 1946; the 45th president of the United States) and Robert Trump (1948–2020; a top executive of his father’s property management company until his retirement).

After Elizabeth’s birth, and with America becoming more involved in World War II, Trump moved his family to Virginia Beach, Virginia. In 1944, as Trump’s FHA funding lulled, they returned to Jamaica Estates, Queens, where Mary suffered a miscarriage. By 1946, they were living in a five-bedroom Tudor-style house Trump built in Jamaica Estates, and Trump purchased a neighboring half-acre lot, where he built a 23-room, 9-bathroom home. The family moved in in 1951, and Fred and Mary remained there until their deaths. The couple was also given an apartment on the 63rd (in reality the 55th) floor of their son Donald’s Trump Tower (c. 1983), which they rarely used.

During World War II, Trump built barracks and garden apartments for U.S. Navy personnel near major shipyards along the East Coast. After the war, he expanded into middle-income housing for the families of returning veterans. From 1947 to 1949, Trump built Shore Haven in Bensonhurst, Brooklyn, which included 32 six-story buildings and a shopping center, covering some 30 acres, and procuring him $9 million in FHA funding. In 1950, he built the 23-building Beach Haven Apartments over 40 acres near Coney Island, procuring him $16 million in FHA funds. The total number of apartments included in these projects exceeded 2,700. In 1963–64, he built Trump Village, an apartment complex in Coney Island, for $70 million—one of his biggest and last major projects. He built more than 27,000 low-income apartments and row houses in the New York area altogether.

Singer Woody Guthrie was a tenant in one of Trump’s apartment complexes in Brooklyn in 1950. In his unrecorded song “Old Man Trump,” he accused his landlord of stirring up racial hate “in the bloodpot of human hearts.”

In early 1954, President Dwight D. Eisenhower and other federal leaders began denouncing real estate profiteers. On June 11, The New York Times included Trump on a list of 35 city builders accused of profiteering from government contracts. He and others were investigated by a U.S. Senate Banking committee for windfall gains. Trump and his partner William Tomasello were cited as examples of how profits were made by builders using the FHA. The two paid $34,200 for a piece of land which they rented to their corporation for $76,960 annually in a 99-year lease, so that if the apartment they built on it ever defaulted, the FHA would owe them $1.924 million. Trump and Tomasello evidently obtained loans for $3.5 million more than Beach Haven Apartments had cost. Trump argued that because he had not withdrawn the money, he had not literally pocketed the profits. He further argued that due to rising costs, he would have had to invest more than the 10% of the mortgage loan not provided by the FHA, and therefore suffer a loss if he built under those conditions.

In 1966, Trump was again investigated for windfall profiteering, this time by New York’s State Investigation Commission. After Trump overestimated building costs sponsored by a state program, he profited $598,000 on equipment rentals in the construction of Trump Village, which was then spent on other projects. Under testimony on January 27, 1966, Trump said that he had personally done nothing wrong and praised the success of his building project. The commission called Trump “a pretty shrewd character” with a “talent for getting every ounce of profit out of his housing project,” but no indictments were made. Instead, tighter administration protocols and accountability in the state’s housing program were called for.

Fred’s son Donald joined his father’s real estate business around 1968, initially working in Brooklyn, and rising to become company president in 1971. He entered the real estate business in Manhattan, while his father stuck to Brooklyn and Queens. Donald later said, “It was good for me. You know, being the son of somebody, it could have been competition to me. This way, I got Manhattan all to myself.” He began calling the company the Trump Organization around 1973. In the mid-1970s, Donald received loans from his father exceeding $14 million. In 2015–16, during his campaign for U.S. president, Donald claimed that his father had given him “a small loan of a million dollars,” which he used to build “a company that’s worth more than $10 billion,” denying that he had inherited $200 million from his father. An October 2018 New York Times exposé on Fred and Donald Trump’s finances concludes that Donald “was a millionaire by age 8,” and that he had received $413 million (adjusted for inflation) from Fred’s business empire over his lifetime, including over $60 million ($140 million in 2018 currency) in loans, which were largely unreimbursed.

Minority applicants turned away from renting apartments complained to the New York City Commission on Human Rights and the Urban League, leading these groups to send test applicants to Trump-owned complexes in July 1972. They found that white people were offered apartments, while black people were generally turned away (by being told there were no vacancies); according to the superintendent of Beach Haven Apartments, this was at the direction of his boss. Both of the aforementioned advocacy organizations then raised the issue with the Justice Department. In October 1973, the Civil Rights Division of the U.S. Department of Justice (DOJ) filed a civil rights suit against the Trump Organization (Fred Trump, chair, and Donald Trump, president) for infringing the Fair Housing Act of 1968. In response, Trump attorney Roy Cohn countersued for $100 million in damages, accusing the DOJ of false accusations.

During the war and until the 1980s, Trump denied that he spoke German and claimed that he was of Swedish origin. According to Trump’s nephew, John Walter, “He had a lot of Jewish tenants and it wasn’t a good thing to be German in those days.” In 1973, Trump claimed to have been born in New Jersey in an interview with The New York Times. Donald Trump’s The Art of the Deal (1987) similarly states that Fred Trump was the son of an immigrant from Sweden and born in New Jersey. Trump’s contributions to Jewish charities led some to believe that he belonged to the Jewish faith. During the 1980s, Fred Trump became friends with future Prime Minister of Israel Benjamin Netanyahu, who at the time was the Israeli Ambassador to the United Nations in Manhattan.

A consent decree between the DOJ and the Trump Organization was signed on June 10, 1975, with both sides claiming victory—the Trump Organization for its perceived ability to continue denying rentals to welfare recipients, and the head of DOJ’s housing division for the decree being “one of the most far-reaching ever negotiated.” It personally and corporately prohibited the Trumps from “discriminating against any person in the … sale or rental of a dwelling,” and “required Trump to advertise vacancies in minority papers, promote minorities to professional jobs, and list vacancies on a preferential basis”. Finally, it ordered the Trumps to “thoroughly acquaint themselves personally on a detailed basis with … the Fair Housing Act of 1968.”

In early 1976, Trump was ordered by a county judge to correct code violations in a 504-unit property in Seat Pleasant, Maryland. According to the county’s housing department investigator, violations included broken windows, dilapidated gutters, and missing fire extinguishers. After a court date and a series of phone calls with Trump, he was invited to the property to meet with county officials in September 1976 and arrested on site. Trump was released on $1,000 bail.

In 1976, Trump set up trust funds of $1 million ($4.5 million in 2019 currency) for each of his five children and three grandchildren, which paid out yearly dividends. Trump appeared on the initial Forbes 400 list of richest Americans in 1982 with an estimated $200 million fortune split with his son Donald. (It was later revealed that Donald’s share of the fortune was closer to $5 million, although he claimed both the family fortune and his share of it was much higher, even using a false identity to make such arguments in 1984.)

Trump was a teetotaler and an authoritarian parent, maintaining curfews and forbidding cursing, lipstick, and snacking between meals. At the end of his day, Trump would receive a report from Mary on the children’s actions and, if necessary, decide upon disciplinary actions. He took his children to building sites to collect empty bottles to return for the deposits. The boys had paper routes, and when weather conditions were poor, their father would let them make their deliveries in a limousine. According to Fred Jr.’s daughter, Mary L. Trump, Trump wanted his oldest son to be “invulnerable” in personality so he could take over the family business, but Fred Jr. was the opposite. Trump instead elevated Donald to become his business heir, teaching him to “be a killer,” and telling him, “You are a king.” Mary L. Trump states that Fred Sr. “dismantled [Fred Jr.] by devaluing and degrading every aspect of his personality” and mocked him for his decision to become an airline pilot. In 1981, Fred Jr. died at age 42 from complications due to his alcoholism.

In 1987, when Donald’s loan debt to his father exceeded $11 million, Fred invested $15.5 million in Trump Palace Condominiums and sold these shares to his son for $10,000, thus appearing to avoid millions of dollars of taxes on Donald’s behalf by masking a hidden donation and benefiting from an illegal tax write-off. In late 1990, when an $18.4 million bond payment for Trump’s Castle was due, Fred used a bookkeeper to purchase $3.5 million in casino chips, placing no bet, helping Donald avoid defaulting on his bonds; this action, illegal in New Jersey, resulted in a $65,000 fine.

In December 1990, Donald sought to amend his father’s will, which according to Maryanne Trump Barry, “was basically taking the whole estate and giving it to Donald,” allowing him to “sell, do anything he wants … with the properties.” The Washington Post wrote that this “was designed to protect Donald Trump’s inheritance from efforts to seize it by creditors and Ivana,” whom he divorced that month. Fred Trump rejected the proposal, and in 1991, composed his own final will, which made Donald, Maryanne, and Robert Trump co-executors of his estate. Trump’s lawyer noted that Fred Jr.’s children, Fred III and Mary L. Trump, would be treated unequally because they would not receive their deceased father’s share, and wrote to Trump that “Given the size of your estate, this is tantamount to disinheriting them. You may wish to increase their participation in your estate to avoid ill will in the future.” In October 1991, Trump was diagnosed with “mild senile dementia”, displaying symptoms such as forgetfulness.

In 1993, Harry Hurt III wrote in his book Lost Tycoon: The Many Lives of Donald J. Trump that he overheard Fred Trump talking about Donald and his wife Marla Maples as they departed for a flight, saying, “I hope their plane crashes,” because then “all my problems will be solved.” According to publisher Simon & Schuster, Mary L. Trump, in her 2020 book, Too Much and Never Enough, recounts “the appalling way Donald, Fred Trump’s favorite son, dismissed and derided him when he began to succumb to Alzheimer’s.” In her book, Mary, a clinical psychologist, diagnoses Fred as a high-functioning sociopath.

Trump began to suffer from Alzheimer’s disease around 1993, by which time the anticipated shares of Trump’s estate amounted to $35 million for each surviving child. In 1997, Trump transferred ownership of most of his apartment buildings, valued at just $41.4 million, to his four surviving children. Trump finally fell ill with pneumonia in mid-1999. He was admitted to Long Island Jewish Medical Center in New Hyde Park, where he died at age 93 on June 25. His funeral was held at the Marble Collegiate Church, and was attended by over 600 people. His body is buried in a family plot at the Lutheran All Faiths Cemetery in Middle Village, Queens. Upon his death, Trump’s estate was estimated by his family at $250 million to $300 million, though he had only $1.9 million in cash. His will divided over $20 million after taxes among his surviving children and grandchildren. His widow, Mary, died on August 7, 2000, in New Hyde Park, New York, at age 88. Her and Fred’s combined estate was then valued at $51.8 million.

In 2004, Trump’s four surviving children sold the apartments they acquired in 1997 (then valued at $41.4 million) for $737.9 million ($705.6 million of which was to Rubin Schron), 16 times their previously declared worth. Hundreds of millions in gift taxes were effectively dodged by undervaluing the assets. In October 2018, The New York Times published an exposé which shows that Fred and Mary provided their children with over $1 billion altogether, which should have been taxed at the rate of 55% for gifts and inheritances (over $550 million), but records show that a total of only $52.2 million (about 5%) was paid. Donald Trump’s lawyer denied allegations of fraud and tax evasion, claiming that “President Trump had virtually no involvement whatsoever with these matters. The affairs were handled by other Trump family members who were not experts themselves and therefore relied entirely upon [licensed attorneys, Certified Public Accountants and real estate appraisers]”. New York State could prosecute individuals on the basis of intentional tax evasion if a fraudulent return form can be produced as evidence; the statute of limitations does not apply in such cases.

In October 2016, in response to a Freedom of Information Act request, the FBI released a small file it had on Trump. It includes a 1986 New York Daily News article on Trump Management’s campaign donations of over $350,000 to New York mayor Ed Koch; the bureau was also possibly concerned about ties to organized crime, but much of the relevant information is redacted. By early 2017, the FBI had also declassified 389 pages from its 1970s investigation of alleged racial discrimination by Trump’s company.

In 2018, The New York Times reported in an exposé on Trump’s financial records that they had found no evidence that he had made any significant financial contributions to charities.

Following Trump’s death, Fred Jr.’s children contested his will, citing his dementia and claiming that the will was “procured by fraud and undue influence” by Donald, Maryanne, and Robert Trump. These three had claimed in their legal depositions that Fred Trump was “sharp as a tack” until just before his death, with Donald specifically denying any knowledge of his father’s mental decline, including his 1991 dementia diagnosis. Barry later privately admitted she knew her father had dementia at the time. Mary L. Trump recounts that in later years her grandfather forgot people he had known for decades, including her, whom he referred to as “nice lady”. In 2020, she sued Donald, Maryanne, and the estate of Robert Trump for having allegedly conspired to both devalue her inheritance from her grandfather and coerce her to sign a settlement, possibly depriving her of tens of millions of dollars.