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In 1959, a 12-year-old Donald Trump went to Paul Onish’s bar mitzvah. Posing with five of his buddies at the party, Donald looks a little chubby in his pin-striped sport coat, his blond hair already swept back in what would become his signature look. Donald’s present to Paul was $5; Onish still has his gift list. The two boys were classmates at the Kew-Forest School, a private school in Queens, and in their seventh-grade class of 30 kids, 16 were Jewish, according to Onish’s accounting based on his old yearbook, “The Blotter.” Not that that mattered: Neither Onish nor several of Trump’s other buddies from those years recalls ever talking about religion with their friend; they were sports fans who loved baseball and soccer, and New Yorkers first and foremost.
Trump was a loud kid, Onish recalls. He was combative, he was a comedian and sometimes it was hard to tell when he was being serious. He would insult others, and then he would say that he didn’t mean anything by those nasty comments. “We were cutups,” says Onish, who was one of Trump’s closest friends in middle school. “He knocked lunchboxes out of people’s hands, he liked to tug on girls’ hair, he was a little [bit] of a jokester.” Onish describes himself and Trump as two of the “worst.”
Trump has long resisted attempts to trace the roots of his character, but he does concede that he was very much shaped by his childhood. In fact, Trump told me last year in one of a series of interviews for The Washington Post’s biography, Trump Revealed, that he hasn’t really changed since he was about seven. And surely what some people can’t stand about him—and what others find refreshingly direct—is that childlike spunk, or, if you prefer, impulsivity. Trump’s early years turn out to say quite a bit about the way he’s run his business and his presidency so far.
For Jews, Trump poses an especially divisive puzzle. Is the man whose oldest daughter—his barely veiled favorite among his five kids—married an Orthodox Jew and converted to Judaism also someone who lacks qualms about cozying up to anti-Semitic extremists? What are Jews to make of a president who has tweeted anti-Semitic imagery and trafficked in stereotypes, saying, “The only kind of people I want counting my money are little short guys that wear yarmulkes every day” or “I’m a negotiator, like you folks”? Does it matter that Trump’s ego wall in his office on the 26th floor of Trump Tower devotes much of its most prominent space to awards, plaques and photos from Jewish and pro-Israel groups? On one day, Trump seems like the best thing to happen to American Jews—the “first Jewish president” as some supporters like to call him—a solid supporter of Israel who has surrounded himself with Jews, both at the Trump Organization and now in the White House. On another day, he issues perplexing communications such as the Holocaust Remembrance Day statement that made no mention of Jews.
During the 2016 campaign, Trump never made overtly hostile remarks about Jews—nothing as harsh as the comments he made about Mexicans, Muslims, blacks or immigrants. And Trump has always denied having an animus toward any group. Whenever I asked Trump about his insensitivity toward one minority or another, he’d look mystified, hurt and sometimes a little angry. “I am the least racist person that you’ve ever encountered,” he told me once, before launching into a story about how Don King, the black boxing promoter, had endorsed him. Similarly, when questions arise about anti-Semitism, Trump’s instinct is to go immediately to the personal—citing his daughter Ivanka’s conversion and marriage to Jared Kushner, or the fact that he now has Jewish grandchildren.
But Trump’s sluggish response to the wave of anti-Semitic vandalism and threats that followed his election has divided opinion within the American Jewish community. Shmuley Boteach, the New Jersey rabbi and best-selling author, says Trump is actually a philo-Semite, with a lifelong history of surrounding himself with Jewish executives, employees and social acquaintances, as well as a strong record of support for Jewish causes and for Israel. Boteach agrees with critics of Trump that the president was late and light about speaking out against the spate of threats against Jewish institutions early this year, and about the spasms of anti-Semitism that flared after the election. But he dismisses as “ridiculous” the warnings of people such as Steven Goldstein of the Anne Frank Center for Mutual Respect, who recently said, “Make no mistake: The anti-Semitism coming out of this administration is the worst we have ever seen from any administration.” Even though Trump offered a full-throated denunciation of Holocaust denial in a Holocaust Remembrance Day speech in April, Goldstein has been far from alone: Doubts about Trump’s views on Jews have come from a number of prominent Jewish organizations, such as the Anti-Defamation League, and from individuals, such as an ad hoc group of nearly 200 scholars of Jewish history who signed a statement noting that Trump “refused to denounce—and even retweeted—language and images that struck us as manifestly anti-Semitic. By not doing so, his campaign gave license to haters of Jews.”
Unlike his critics and opponents, Trump doesn’t see a natural connection between his sharp tongue and any underlying antipathies; rather, his insults and barbs are, to his mind, either meant as a joke or are just part of the frank, straight-shooting personality that he credits with getting him where he is today. If that defense sounds like what some American Jews say about their own grandparents’ politically incorrect language, that’s no accident. Trump’s vocabulary and style emerged from the birthplace of much of American Jewry—the rough-and-tumble of New York City in the mid-20th century.
In their stately home in Jamaica Estates, then an affluent, largely Jewish neighborhood in Queens, Fred and Mary Trump raised their five children with little emphasis on religion. Donald and his siblings were brought up as mildly Presbyterian kids who occasionally attended Norman Vincent Peale’s “power of positive thinking” sermons at Marble Collegiate Church in Manhattan. Donald’s attention was more focused on the streets. He grew up playing with his friends, many of them Jewish, going to each other’s houses to trade baseball cards and play marbles.
The Trumps were among the wealthier families in Jamaica Estates. The 23-room Trump home on Midland Parkway was for some kids the cool place to go—they had a color TV, a cook, a chauffeur, an intercom system and an elaborate model train set that sticks in his classmates’ memories even half a century later. “He had the most amazing trains,” recalled Mark Golding, a childhood friend from ages six to 13, who along with Trump attended Onish’s bar mitzvah. “He had all these special gadgets and gates and switches, more extensive than anything I’d seen. I was very envious.”
The Trump home was also more formal than most in the neighborhood; the other boys knew Fred Trump—a Republican who nonetheless spent most of his weekends schmoozing Brooklyn’s Democratic power elite—as a stickler who didn’t allow any bad language in his house, and who reacted sharply if he heard of any misbehavior at school. But there was plenty of that: Donald loved horseplay. Even six decades ago, friends say, he had the same impish smile that sweeps across his face now when he’s caught in a mischievous exaggeration.
Donald got into trouble so often that Fred Trump finally had his fill. The last straw was his discovery that Donald and his friend Peter Brant (who also appears in the Onish bar mitzvah photo), had secretly been sneaking across the bridge to Manhattan on Saturdays after soccer. Hungry for autonomy, the boys explored Central Park, watched black men play basketball on outdoor courts near the East River, gawked at Times Square panhandlers, ate hot dogs from street vendors and savored egg creams at diners. They took in West Side Story on Broadway and, inspired by its portrayal of New York street gangs, invented a game they called “Land,” in which they traded turns throwing switchblades into the ground and twisting their bodies to follow the path of the knives. When Fred Trump found out about the knives, he decided his son needed a radical change. He pulled Donald from Kew-Forest in eighth grade and packed him off to New York Military Academy, a boarding school near West Point where discipline was strict and rules were legion.
At military school, Donald’s academic performance was good but not stellar; he didn’t make the class top ten, but he was on the honor roll for four of his five years. He was better known as an avid athlete, captain of the baseball team and a savvy operator in the campus social hierarchy. The military school didn’t attract many Jews, but there were a few, including Trump’s junior year roommate, Ted Levine. In one infamous incident recounted by Levine and others in the class, Trump was the junior supply sergeant in Company E, and one of his duties was to inspect the dorms. When he found that Levine’s bed was unmade, Trump tore the sheets off and dumped them on the floor. Levine threw one of his combat boots at Trump and hit him with a broomstick. Trump retaliated by grabbing Levine and pushing him toward the window. Witnesses said Levine would have gone out the window if two other cadets hadn’t intervened. But neither Levine nor other schoolmates attributed Donald’s rough behavior to any animus against Jews, and Levine and Trump got along well enough as roomies, even if Levine did later say that Donald would try to “break” anyone who failed to bend to his will.
Trump started college at Fordham University in the Bronx, commuting to the mostly Catholic school from his Queens home. At a time when many young people were rebelling against rules and institutions, Trump often showed up for class in a three-piece suit, carrying a briefcase. One of his friends, Robert Klein, an accounting major who sat next to him in his accounting class, took note of Trump’s doodles. The future developer was drawing buildings—skyscrapers. Trump was unimpressed by his fellow students at Fordham; as one friend, Brian Fitzgibbon, put it, Trump’s “wealth and the fact that he was not Catholic may have made him feel different from others.” Trump sometimes complained that “there were too many Italian and Irish students at Fordham,” Fitzgibbon added. Trump wanted to move up to the Ivy League, and after his sophomore year, he got into the University of Pennsylvania as a transfer student. He never even said goodbye to his teammates on Fordham’s squash squad.
At Penn, where Trump was enrolled in the undergraduate business program in the Wharton School, he found a crowd more to his liking, including the scions of some of the country’s most prominent real estate developers. Trump told friends that he’d figured out his future—he wanted to be the next Bill Zeckendorf, one of Manhattan’s most successful developers and a major contributor to Jewish charities. Never much of a student, Trump spent much of his time in Philadelphia scouring the neighborhood for apartments he could buy to rent out to students. On weekends, he usually returned home to New York, collecting rents and chatting up tenants with his father as they moved around the mostly Jewish sections of Brooklyn where their properties were clustered.
Throughout his college years and after he graduated, Trump continued his apprenticeship in the family business. His hero, then as now, was his father, a demanding entrepreneur with a knack for selling himself as a brand. Trump apartments, advertised on banners flown over the beaches of Brooklyn, were a mainstay of the middle-class sections of Brooklyn and Queens that were heavily populated by Jews moving out of crowded Manhattan.
Fred Trump was himself the son of a German immigrant. Donald’s mother came to America as a teenager from Scotland. But through the years, Fred Trump, who died in 1999, often told people that he was actually from Swedish stock, not German. Donald Trump knew the story when I asked him about it. “Some people thought that” his father was from Sweden, and “some people think I’m Swedish,” he said. Trump wouldn’t comment on whether his father had planted that notion to steer clear of any anti-German bias among the Jewish renters who dominated the population at Trump Village, Fred’s 3,800-unit development in the Coney Island section of Brooklyn. The sprawling array of apartment towers was a step up for striving middle-class families, many of them Jewish immigrants or their children, who enjoyed the ocean breezes and proximity to Nathan’s hot dog stand and Mrs. Stahl’s Knishes on the beachfront boardwalk. The rationale behind Fred Trump’s tale about being Swedish was clear to his nephew John Walter, the family’s historian: Fred Trump “had a lot of Jewish tenants and it wasn’t a good thing to be German in those days.”
Over the years, Fred Trump grew ever more reticent about his German heritage. Although he was fluent in the language, he denied it in later life and did not teach his children German. The bit about being Swedish was only one piece of his effort to assure that no one would turn away from Trump housing because of the owner’s heritage. Much of the Brooklyn Democratic political establishment, politicos who could make or break his zoning and property deals, were Jewish, and Fred often took Donald with him on his weekend rounds of the Democratic clubs. Fred made such a habit of donating to Jewish charities—he served as treasurer for an early Israel benefit concert at Ebbets Field—that many Jews assumed he was part of the tribe himself. (At Trump Village, where several members of my grandmother’s family lived, it was taken as gospel that the Trumps were secretly Jewish. That was, as the president might say, fake news.)
Over the years, Fred Trump grew ever more reticent about his German heritage. He “had a lot of Jewish tenants and it wasn’t a good thing to be German in those days.”
Fred Trump was careful to try to avoid the ethnic rivalries and confrontations that had turned some New York neighborhoods into battlegrounds. In the 1950s, after Fred constructed a 2,700-unit apartment complex called Beach Haven near Coney Island, he worked to quiet tensions between Jewish teens in his development and Italian kids in nearby Gravesend. Fred built a recreation center—and put out press releases about it—that helped calm the situation.
As Trump family biographer Gwenda Blair reported in her 2001 book, The Trumps, Fred Trump was so deeply embedded in New York’s Jewish social world that he sometimes took the kids in the family limousine and headed up to the Concord resort, the Borscht Belt hotel in the Catskill mountains, where many of the city’s affluent and influential Jewish families took their summer holidays. While Fred would schmooze with power players from the worlds of politics and real estate, Donald, who spent most of his summers at two expensive Christian camps in the Catskills, would join the other kids playing sports and eating from the Concord’s endless trays of kosher food.
As Donald Trump took on a more active role in his father’s business, he developed a belief that the best way to assure that the company’s finances were honestly and efficiently handled was to entrust the work to Jews. From early on, the Trumps showed a preference for renting to Jews. In the early 1970s, when the family was managing thousands of apartments, a Trump rental agent told federal investigators that the company sought to rent only to “Jews and executives.” Another agent recalled in a court filing that “Trump Management believes that Jewish tenants are the best tenants.” The Trumps had become the targets of a federal discrimination lawsuit that accused them of systematically denying housing to blacks and Hispanics. The government’s investigation found that rental agents at the Trump management office would tag applications from minority applicants with a “#9” or with “C” for colored, and those potential customers would either be told that no housing was available or would be steered to less desirable locations.
The Justice Department’s civil rights case against the Trumps was led by a young Jewish lawyer, Elyse Goldweber, who had found out from housing activists and Trump company employees that only one to four percent of Trump tenants were minorities—far below the percentage of the local population. At 26, Goldweber led the investigation and took on one of New York’s biggest developers; as the case dragged on, she was replaced by another Jewish attorney, Donna Goldstein. Her religion was of course irrelevant to the lawsuit, or so it seemed until Trump’s attorney accused Goldstein in court papers of conducting a “Gestapo-like interrogation.” The Trump lawyer asked the court to hold the Justice Department attorney in contempt. The judge didn’t buy it, and Trump eventually had to settle the discrimination case, agreeing to rent to black and Hispanic customers and taking out ads in New York newspapers attesting to that pledge. But scorched-earth legal tactics like the attack on Goldstein would become a trademark of Trump’s litigious way of doing business. His attorney in that case—and his mentor in business and politics for years to come—was Roy Cohn, in many ways the most significant man in Trump’s life after his father.
In 1973, Trump, then 27, crossed the bridge into Manhattan, starting his own real estate business, outside the safety of his father’s empire and exactly where Fred Trump had warned him not to go—into the city’s most competitive and difficult market. To smooth the way, Trump joined Le Club, a members-only social spot frequented by rich people, social climbers and a mix of political types and business machers. There, one night, Trump met Cohn. At 46, Cohn, the son of a prominent Jewish judge, had already prosecuted Julius and Ethel Rosenberg as Soviet spies and had served as Senator Joseph McCarthy’s right-hand man during the anti-communist witch hunts of the 1950s. He was one of New York’s best-connected fixers, with a long list of boldfaced name clients, including prominent mobsters, politicians and business moguls.
Cohn advised Trump not to cave to the government’s pressure to settle the race discrimination case, but rather to “tell them to go to hell and fight the thing in court”—to counterattack with bias accusations against Goldstein and to countersue the Justice Department. Trump came to depend on Cohn not only for legal advice, but for the core tactics that would define Trump’s approach to doing business: Never admit fault. Never express regret. When you’re criticized, hit back ten times harder. And use the news media to attack and to build your personal brand.
During this period, Trump would talk to Cohn several times a day. They then would spend evenings at Studio 54, where Cohn introduced Trump to celebrities and politicians. They worked together on deals, and Cohn aggressively pursued Trump’s interests with the National Football League, the government and competing businesses.
For many years, Trump kept a framed photo of Cohn on his office desk, not so much as an homage to his most important adviser, but as a weapon to be wielded against any contractor or vendor who was pushing too hard to be paid—an implicit threat that if things didn’t go as Trump wanted them to, someone might have to face the fearsome Cohn. At a roast of Cohn at Studio 54, Trump once said that when disputes arose in his business, “we just tell the opposition Roy Cohn is representing me and they get scared. He never actually does anything.”
With Cohn on speed dial, Trump built his own empire, starting with his renovation of the Commodore Hotel into the Grand Hyatt in 1980. In 1983, with Cohn still at his side, Trump opened his crowning achievement, the 58-story Trump Tower on Fifth Avenue. But in 1984, when Cohn was diagnosed with AIDS, Trump distanced himself from his longtime friend. “I can’t believe he’s doing this to me,” Cohn said, according to Wayne Barrett’s biography, Trump: The Deals and The Downfall. “Donald pisses ice water.” When Cohn died in 1986, Trump came to the funeral but stood in the rear of the chapel.
Through most of the following three decades, no single adviser played as vital a role as Cohn had, but Trump entrusted his operations to a tight, loyal group of executives and attorneys, many of them Jewish: Jason Greenblatt, an Orthodox graduate of Yeshiva University, has been Trump’s real estate attorney for two decades (and is now a Trump adviser on Israel); David Friedman, whom Trump has named as ambassador to Israel, did bankruptcy work for Trump at a rough time in the company’s history; Trump’s longtime personal attorney, Michael Cohen, served the Trump organization in prominent positions for many years and is now a deputy national finance chairman of the Republican National Committee.
Attorney Roy Cohn—Donald Trump’s mentor in business and politics—was in many ways the most significant man in his life after his father.
Trump sometimes averred that Jews made better accountants and attorneys, according to friends and longtime employees, but his affinity for Jewish employees was not limited to particular skills he had stereotyped the Jews as excelling in. He liked to be surrounded by guys, Jewish or not, from the outer boroughs—men who, like him, felt snubbed by the wealthy Manhattan social elite. Whether he was eagerly courting the respect of The New York Times or trying to beat Manhattan’s old-line real estate families to control top-shelf properties, he always saw himself as the underdog trying to make it in the big city. “I was a kid from Queens who worked in Brooklyn,” he wrote in Trump: The Art of the Deal. Then, when he moved to Manhattan, “suddenly I had an apartment on the Upper East Side. I became a city guy instead of a kid from the boroughs.”
Trump’s executives describe him as caring, generous and respectful, even if he did yell a lot and call them at all hours to handle minor issues. Trump was so loyal to his top executives that “we always felt that if you were close enough to Donald that he would have to be the one to let you go, you had a job for life,” said Barbara Res, who was head of construction on Trump Tower and worked for Trump for more than ten years. In turn, Trump says the attribute he values most in employees is loyalty. Those who’ve worked for Trump for decades say he doesn’t talk about the fact that so many people around him are Jewish, but he often attended their children’s bar and bat mitzvahs, made sure they could get away from work for Jewish holidays, and participated in Jewish charity events that they supported.
A Trump Organization executive who asked not to be named because he was not authorized to speak to the press said that the key to understanding his boss’s relationship with Jews was Trump’s lifelong sense that he must work harder than anyone else because the people born to power had never accepted his family. “Donald has always seen himself as an outsider,” the executive said. “That’s why he can connect with middle Americans who you wouldn’t think of as connecting to a billionaire. He wouldn’t say it this way, but for him, Jews are kind of like him—on the outside, always working to get in.”
Marc Fisher, a senior editor at The Washington Post, is co-author, with Michael Kranish, of Trump Revealed: An American Journey of Ambition, Ego, Money, and Power.