All in the Family: The Trumps and How We Got This Way

INTRODUCTION

DEARLY DEPARTED

I had no idea what we were in for.

June 29, 1999. On the day we buried my grandfather Fred Trump, whose name I carry and whose legacy I still bear, my son William Trump was just about to burst into the world. And I didn’t have a clue what a long, dark shadow that first family milestone was going to cast on the second one… or which of my relatives had been secretly plotting to leave one branch of the family out in the cold.

Mine.

My father’s father was the Trump who first defined what it meant to be a Trump, long before Uncle Donald marched the family name into Manhattan and gave it that shiny 1980s glow. It was sad for Grandpa to leave us, of course. But he was ninety-three and had been struggling with dementia for years. Six years earlier, when he was best man at Donald’s wedding to Marla Maples, my grandfather had almost gotten lost on his way to the altar and had to be reminded what he was doing there.

There wasn’t a wet eye in the place, writer Julie Baumgold blurted to a New York Times reporter that awkward evening at the Plaza Hotel, after the I do’s. Just the kind of media snark we’d all been forced to get used to.

My grandfather had lived what could only be called a long and prosperous life. Having worked since he was a skinny ten-year-old, he’d risen to the very pinnacle of the New York real-estate world, ending up with a stunning portfolio that included scores of high-rise apartment buildings in Brooklyn and Queens. He had political juice from City Hall to Albany and was known everywhere he went, which is to say the outer boroughs of New York City, Grossinger’s in the Catskills, and the Fontainebleau Hotel in Miami Beach. But he’d had a terrible relationship with my father, who blamed him for ruining his life. It was one of those can’t-live-together, can’t-live-apart situations. But it was my father, his namesake, who died just shy of his forty-third birthday with an ex-wife and two teenage children. So, you tell me: Who paid the ultimate price?

My grandfather wasn’t the easiest man to get along with. After all the tense holiday dinners I’d sat through at my grandparents’ twenty-three-room Colonial mansion in Queens, believe me, I knew. That was as plain as the three-piece suits, slicked-back hair, and Walter Cronkite mustache that became my grandfather’s fashion signatures. He was an old-style patriarch, presiding over a large, rambunctious family, whose members he managed to dominate and sometimes pit against each other. But business was his passion—that’s how he always defined himself, as a hard-driving businessman. In the office and at home, he had an emotional range that went all the way from stoic to judgmental to really pissed off. Not a lot of cuddling on the couch, and his later-in-life confusion didn’t add much humility to the mix. In his prime, he’d been an undeniably commanding figure and a very present grandfather. There was no doubt he’d amassed a stunning list of accomplishments in those nine-plus decades of his, along with a fortune worth at least a couple of hundred million dollars. And you can’t explain the personalities of any of his five children without knowing what he did for—and to—each of them.

Maryanne, the whip-smart but often cruel eldest child, whose public achievements as an attorney and federal judge were equally matched by her constant carping within the family.

My father, Fred Trump Jr., the charming black-sheep first son, whose free-spirited rejection of the family business was taken as a character flaw almost as severe as his self-destructive impulses and his alcoholism.

Elizabeth, the quiet middle child, who did everything she could to avoid the blinding glare of the Trump-family spotlight and almost succeeded.

Hard-charging Donald, the one most like their father, whose ferocious ambition and drive had to compensate for a lack of compassion, subtlety, and book smarts.

And finally, Robert, the chameleon little brother, who landed on one side or another of each fresh family drama, depending on who appeared to be ascendant that week.

No one can deny their many accomplishments. Grandpa built all those buildings and housed thousands of people, but he never achieved the intellectual stature that his daughter Maryanne did. He never became world-famous like his son Donald. He never sought that out. He certainly never hosted his own hit TV show or got himself elected president. But his towering presence launched all that and so much more, some of it worth being deeply proud of, some of it much better ignored. And that is the story of one generation of our family, all wrapped up in one paragraph.

I never planned to write a book. Up until now, I have stayed stubbornly quiet, even as those around me took their potshots. But silence is golden only when there is nothing that needs to be said. We are all in this family together, even when the together part isn’t close to where it ought to be. Well, it’s time for me to open up now, let some light shine in, and reflect on how we got this way so we can move past all that stuff. I have a name—Trump—that is extraordinarily polarizing, and keeps getting more so. But there is more to my name than all that friction, and I am ready to use it for something good. A cause near and dear to my heart: advocating for individuals with developmental disabilities. But we’ll get to that in a bit.

This nation and this family are inextricably intertwined. As go the Trumps, so goes America. For the sake of my generation and the generations to come, as well as the great nation we love, it’s time to advocate for policy over politics.

I realize the chapters ahead may ruffle some feathers. Things could be tense on the golf course the next time Uncle Donald rolls up in his cart. And I am certainly a flawed messenger. I have my faults—many of them. Who doesn’t in this family… or any other? The difference between me and my relatives is that none of them will admit that, and I just did. Thanks to some circumstances unique to my own life, I am a different kind of Trump.

So where did the cruelty come from? I’ve wrestled with that question for years. Who planted the seeds of narcissism? When did winning become everything? How did Trump loyalty become such a one-way street? Were all the outsized achievements in spite of these complicated relationships… or because of them? And what does all this mean for my generation of Trumps—David Desmond (Maryanne’s son from her first marriage), Donald Jr., Ivanka, Eric, Tiffany, Barron, my sister, Mary, and myself—and for our children and the generations that follow?

Excellent questions, and I will try to address all of them.

The cruelty, I can now see, didn’t come from any one of those distinct Trump personalities. As I will explain, it came from the unique way these strong-willed family members collided with each other and anyone who ever stood in their way. And a lot of it started with my grandfather.

Which brings me back to his send-off. He certainly deserved a proper one.

Six hundred and fifty people packed the pews at the Marble Collegiate Church on Fifth Avenue, a pulpit made famous by The Power of Positive Thinking author Norman Vincent Peale. Various Trumps had attended services there since the 1960s. It was quite a turnout that broiling June day. Relatives. Employees. Business associates. A who’s who of machers from the worlds of New York politics, media, construction, and real estate. The only thing missing… friends. Old and single-minded as he was, Grandpa didn’t have too many friends at the end.

My wife, Lisa, and I arrived at the church two minutes late. What the fuck…, my aunt Maryanne snapped at us as we slipped in the back and headed up to the family pew. I didn’t bother to answer. I just motioned toward Lisa’s belly. She was nine months pregnant, already out to here, but not wanting to miss such an important family gathering. My superwoman of a wife had willed herself there.

I’d been asked to deliver one of the eulogies, along with my grandfather’s four living children. Maybe I was a stand-in for my missing father.

Naturally, Donald spoke mostly about Donald. I was having the greatest year of my business career, he began, a heavily edited portrayal of his ever-changing fortunes. I was sitting having breakfast thinking about how well things were going for me, when he got the news that his father had died.

When it was my turn to speak, I got up there and looked out at all those people. It was the largest crowd I had ever addressed. I took a different path from the other eulogists. I didn’t even want to mention my grandfather’s wealth.

I accentuated the positive, saluting his potent influence on his family and his city. But I also wanted to touch on the hard history between my grandfather and his oldest son, which still hung so heavily over the family almost eighteen years after my father’s demise. One of them was completely driven, I said. The other was a total free spirit. After all their clashes, maybe the two of them can find peace and comfort together in the afterlife.

We could hope, right?

I caught Ivana’s eye just as I was saying that. After marrying twenty-two years earlier in this very same church, she and Donald had been divorced for eight and a half years by then. But she had been close to her father-in-law. Just as I got to peace and comfort, Ivana began to sob. Then, I spoke directly to my grandmother. I’d always had a special connection with her and she with me. Like my father and like me, she’d sometimes felt like an outsider in her own family. I wanted to bring some kind of encouragement to her.

Gam, I said, don’t worry. Your fellows are going to be okay.

I don’t know where I got that. I’m not even sure I fully believed it. But in a family not always known for its small kindnesses, it felt like the right thing to say.

On that sad day, I had every reason for optimism, though I didn’t choose to brag about it like some people had. My own real-estate career was hitting its stride—and not inside the protective womb (or the snake pit) of the Trump Organization, where Donald was now president, CEO, and twenty-four-hour-a-day publicity machine. I was beating a professional path all my own. Lisa and I had two happy, healthy children—five-year-old Andrea and three-year-old Cristopher—and a house we loved in Connecticut. We were delighted to know that our family would soon be welcoming another baby boy, the third child we had both been hoping for.

My precious son William was born the next morning. And without the tiniest heads-up, our whole world would suddenly be turned upside down.

PART I

MAKING US

CHAPTER 1

FRED ZERO

It’s tempting to start the story of the Trumps with my grandfather, the man everyone called Fred Trump Sr.

Tempting but wrong.

The real story of the Trumps doesn’t begin with him. It doesn’t even begin with Trump. The original family name in the Pfalz region of southwest Germany was Drumpf, though the two spellings don’t sound all that different if you mumble them in a strong enough German accent.

Various genealogists, amateur and professional, have tried to trace our family tree. They differ on key details, but they all seem to mention a man named Johannes Philipp Drumpf, who was born in 1667 and married a woman named Juliana Maria Rodenroth. They had a son named Johannes (1699), who had a son named Johann (1727). That Johann had a son or maybe it was a grandson named—guess what? Johannes, the German version of John, was clearly the Fred of its day. That Johannes was born in 1789 in Bobenheim am Berg before settling in the quaint Bavarian village of Kallstadt, which was also where he died. It went on like that for a while longer. It’s impossible to say exactly when Drumpf morphed into Trump or why. But it wasn’t until March 14, 1869, when my great-grandfather was born, that things started to get interesting. He was Friedrich Heinrich Trump, the original Fred Trump.

If my grandfather was Fred Sr., what does that make my great-grandfather?

Fred Zero?

As the youngest son, he did not get off to an especially promising start. But the details of his life are a remarkably prescient foreshadowing of Trump adventures generations into the future.

People haven’t paid nearly enough attention to this part of our family history. It really shows the road map of things to come.

For centuries, the people of Kallstadt grew plump grapes and made crisp, delicious wines. I’ve never been there. I was hoping to visit during my college study-abroad program. I went skiing in Innsbruck instead. Sorry, Kallstadt. But from the pictures I’ve seen, it’s a beautiful place of old stone buildings, rolling hills, and sturdy glassware in every living room. In the 1880s, there weren’t many opportunities in Kallstadt for a young man who wanted to make a name for himself but didn’t have much going for him. Friedrich, or Fred Zero, was a sickly child, considered too weak to work in the family vineyards with his five brothers and sisters. So, at age fourteen, he apprenticed with an experienced barber in nearby Frankenthal. But after returning to Kallstadt, he discovered that there wasn’t enough business in his village of a thousand people to make a decent living shaving whiskers and snipping hair. And there was one other issue staring him in the face: He was approaching the age for the military draft, which started as early as seventeen. Having absolutely no interest in joining the army, he decided he would follow his mother’s advice and emigrate to America.

(Making a quick note here: My uncle Donald wasn’t the first Trump to sidestep military service.)

On October 7, 1885, my sixteen-year-old future great-grandfather boarded the newly built, iron-screw steamship SS Eider in the German maritime city of Bremen, carrying a single, bulging suitcase and a fistful of dreams. Traveling alone, he arrived ten days later at the Castle Garden Emigrant Depot in New York City.

Welcome to America, young man!

And this is where the Trumps’ American adventure begins in earnest.

The sixteen-year-old had no money. He didn’t have much English or so much as a high school diploma from back home. He could read and write… in German. Beyond that, he was lost. He did have an older sister, Katherina, who’d come to America a few years earlier to join her fiancé, Fred Schuster (another Fred). By the time Friedrich arrived, the couple had gotten married, had a baby girl, and were living in a tiny cold-water apartment in a ragged brick tenement building on Forsyth Street on Manhattan’s Lower East Side. This sister and her husband were the full extent of the connections Friedrich had, the only people with any chance of smoothing his arrival in America.

And still, he was only two generations away from a president of the United States. What Friedrich Trump had going for him was drive.

Putting his childhood frailties behind him, young Friedrich discovered an extraordinary bravado inside himself and vowed to embrace every last opportunity this New World might deliver to him. The original Fred Trump was more than ready to ride the American Dream as far as he could.

His sister and her husband made room for him in that small apartment on the Lower East Side, a teeming neighborhood of newcomers that included quite a few immigrants from their part of Germany. That afternoon, Friedrich met a German-speaking barber who had an empty chair to fill. The ambitious young immigrant went to work the next day.

Barbering helped to get him settled in America, and he stuck with it for the next six years. But my great-grandfather wasn’t about to spend his entire life with a leather strop at the ready and a straight razor in his hand. He had bigger plans and a real fearlessness about fulfilling them. He would soon become the first Trump in history to try his hand in the overlapping businesses of real estate and hospitality, showing promise in both those fields.

(Yes, there were Trump-owned hotels even all those generations ago…)

In November 1891, when he was twenty-two years old, he moved across the country to Seattle, where he bought a piece of property on the outskirts, then opened a restaurant on Washington Street in the city’s raucous Pioneer Square, a lively district of saloons, gambling parlors, and brothels. He called his new business the Dairy Restaurant and offered food, booze, and very likely the same Private Rooms for Ladies its predecessor, an establishment called the Poodle Dog, advertised. The gentlemen were invited upstairs for what I have to assume was something more than conversation and chamomile tea.

It was in Seattle the following October that Friedrich Trump became a United States citizen (it was that easy back then), just in time to officially Americanize the spelling of his first name. Friedrich became Frederick. He registered to vote and cast his first ballot in the 1892 presidential race. I can’t say which candidate he voted for. There is no record of that. But I do know the race was a hard-fought rematch between Benjamin Harrison, the Republican incumbent, and Grover Cleveland, the former Democratic president who was beaten by Harrison four years earlier. Cleveland’s victory was historic, making him the first-ever president, and the only one to date, to serve nonconsecutive terms in the White House.

Sound familiar? History does have a way of repeating itself. I’m not saying this is some kind of omen, from 1892 to 2024. But for what it’s worth, the challenger won the rematch that time, beating the incumbent 46 to 43 percent, with a third-party candidate collecting 8 percent of the vote.

My great-grandfather did well out West, especially during the Klondike Gold Rush of the late 1890s. He never actually mined any gold. Not personally. But he sold his Dairy Restaurant in Seattle and opened a successful saloon, restaurant, and boardinghouse in the mining boomtown of Monte Cristo and even got himself elected justice of the peace. And when the Monte Cristo boom went bust, he moved further north to open, with a partner, the New Arctic Restaurant and Hotel in Bennett, British Columbia, and then the Arctic Restaurant in White Horse, Yukon Territory. Again, instead of mining gold, he mined the miners, to quote Gwenda Blair, whose impeccably researched 2000 book, The Trumps, is still the deepest dive anyone has done into this long-ago era of our family history.

And what were these establishments like? Well, the reviewer for the Yukon Sun praised the Arctic’s excellent accommodations for single men, but added a note of caution: I would not advise respectable women to go there to sleep as they are liable to hear that which would be repugnant to their feelings and uttered, too, by the depraved of their own sex.

A lot of moaning, I guess. Putting the wild in the Wild West.

The businesses were undeniably profitable, as the flesh trade often is. His sisters back in Kallstadt didn’t ask too many questions, but they greatly appreciated the gold nuggets their brother kept sending in the mail. When my great-grandfather returned for a visit in 1901, he arrived a wealthy man, at least by the standards of his modest village. It was on that visit that he met and married a local girl named Elisabeth Christ. It wasn’t long after that he moved with her to New York City, where their first child, a daughter they named Elizabeth, was born in 1904. But the family didn’t stay in New York for long. The new Mrs. Trump was terribly homesick. She claimed she could not tolerate the climate in New York. And she hated the idea of raising children so far from her own family. With Fred’s agreement, they returned to Kallstadt later that year, with hopes of remaining in the Old Country for good.

But a piece of lingering business put an end to that.

In February 1905, Frederick Trump was ordered by royal decree to leave the kingdom of Bavaria within eight weeks for failing to perform his mandatory military service all those years before. My great-grandfather, conscientious objector or draft dodger… and not the last in the family.

There would be no repatriation for him. The decree didn’t mince words. It ordered American citizen and pensioner Friedrich Trump (still spelled the German way) to leave at the very latest on 1 May… or else expect to be deported.

Royal decrees were serious business.

My great-grandfather tried to plead his case. He wrote a fawning letter to Prince Regent Luitpold, addressing the prince as the much-loved, noble, wise and righteous sovereign and sublime ruler. The suck-up letter did no good. On July 1, 1905, the Trumps left on the Hapag steamship Pennsylvania, bound again for New York City, this time to stay.

One other development worth noting: Six months before they boarded the boat, Frederick and Elisabeth Trump conceived a second child. The baby wasn’t born until three months after they landed in America. That baby was my future grandfather Frederick Christ Trump.

It’s the classic immigrant story. From Germany to America. From rags to riches. From pinched horizons to unimaginable opportunity. It has back-and-forths and fits and starts and a few seamy stops along the way. Under the laws of today, my great-grandfather’s original arrival could certainly be considered illegal. He would have been classified as an unaccompanied minor unless his sister Katherina, who’d preceded him here, had taken official steps to be his legal guardian, in which case the whole family could promptly be denounced for abusing the practice of chain migration.

None of that happened to my great-grandfather. America had greeted him with open arms and opportunity, as long as he did his part. For him, Germany was fully in the past.

He and his family, soon joined by a third child, John, settled into an apartment on East 177th Street in the Bronx, where the children spent their early years, before they all moved to a more suburban block in Woodhaven, Queens. Ever the industrious businessman, my great-grandfather got busy building a whole new New York career for himself. No more brothels this time for the father of three.

He was a multitasker before anyone knew the term. He opened a barbershop on Wall Street. He bought property on Jamaica Avenue in Queens. He managed the small Medallion Hotel on Sixth Avenue at 23rd Street in Manhattan. Things got a little dicey for him after Congress declared war on Germany in April of 1917 and the U.S. entered what was then called the Great War (we know it now as World War I). Eager to avoid the growing anti-German sentiment taking hold across America, my grandfather relied instinctively on his salesman’s charm to downplay his German ancestry. No more danke schöns and bitte schöns on the New York sidewalk. With his skill and drive, even the rising prejudice couldn’t slow him down. A landlord, a business owner, a hotel operator—he had every reason to think that the future was bright for him, that he could keep marching ever forward on this immigrant journey of his. America, he kept discovering, really was a land of endless possibility for him and his young family.

And so it was until May 29, 1918.

On that bright morning, he was walking with his twelve-year-old son, Fred, when he suddenly felt unsteady on his feet. He wasn’t sure what the problem was, but he went home to bed. My great-grandfather never even made it to the hospital. By the next morning, he was dead at forty-nine. What was first diagnosed as pneumonia turned out to have been an early case of the so-called Spanish flu.

The Spanish flu didn’t actually come from Spain. That was one of its many misconceptions. The outbreak almost certainly originated in America, perhaps at Fort Riley in Kansas, where the first case of the virus was recorded. It was said that overcrowded and unsanitary conditions created a fertile breeding ground.

An estimated twenty-one to fifty million people died around the world from that earlier pandemic, nearly 700,000 of them in America, many times larger than the death toll of World War I. And it left my great-grandmother an unexpected widow with three young children alone in New York, a city she’d never wanted to be in and now couldn’t leave.

And there it was, another neat foreshadow for the Trump family: The Great Influenza of 1918–1919 was the COVID of its time, another sweeping pandemic that came out of nowhere and suddenly seemed to change just about everything.

It’s strange, but through most of my life, I barely heard a word about my great-grandfather. It was as if the Trump family wasn’t hatched until my grandfather came along. Not a single story about the original Fred Trump. His dramatic immigration journey, his outsized personality, his wild adventures out West, his striking successes in what would become the thoroughly Trumpy trades of hospitality and real estate—his extraordinary life would set a standard for generations to come, especially for my grandfather and my uncle Donald.

And yet… silence.

There were no colorful tales about his many adventures in Germany and America, no ancestral portrait in the hall. It was like Fred Zero got chopped right off the family tree. When his name came up at all, he was only described as gone, as if he’d abandoned the family and moved off somewhere. As a kid, that was the impression I had, which could not have been any further from the truth. Not only did my great-grandfather die in a worldwide pandemic, he left his wife and children with a tidy estate. And he clearly set a compelling example for his older son. But you wouldn’t have known any of that from the Trump family lore. I met my great-grandmother a few times when I was little. I didn’t know to ask about her late husband. And I don’t remember my grandfather ever once mentioning him.

When I finally saw a photo of him, I was struck by how much he looked like all the other Trump males. The prominent nose, the pinched mouth, the big, bushy eyebrows—they were every bit as notable a legacy as any property my great-grandfather left behind. In the late 1990s, when Gwenda Blair was researching her Trump-family history book, Donald called and asked me to speak with her. I told him I’d prefer not to.

Okay, pal, he said. I understand.

I was driven at that point to keep a level of privacy for my family.

CHAPTER 2

GO-GETTER

As if she hadn’t had enough to worry about already…

With the nation still at war and a deadly pandemic rampaging across the land, now my widowed great-grandmother had to manage her grief and face her uncertain future as a single mother.

Elisabeth Trump wasn’t exactly destitute. Her entrepreneurial husband had left her with a two-story, seven-room home in Queens, five vacant lots, $4,000 in savings and life insurance, $3,600 in stocks, and fourteen mortgages, according to Trump biographer Gwenda Blair. His net worth at death was $31,359… in 1918 dollars, which would be in excess of $675,000 today. That part was fortunate. But was it really enough for his widow to make a comfortable life for herself and her three young children? How would she care for them in fast-paced (and high-priced) New York City? How would she feed, clothe, and educate them until she could send them off on their own? She was a thirty-eight-year-old woman with no obvious job prospects and no family to turn to in her time of sudden need.

At least she didn’t think so. That’s when her go-getter of an older son stepped up.

Twelve-year-old Fred hadn’t yet started at Richmond Hill High School when his father passed away. But he had always been an industrious and resilient child. The family lore is filled with tales of my future grandfather’s prodigious work ethic from an absurdly early age, even before his father died. At ten, he’d strapped a large wire basket on the front of his bicycle and taken a job as a delivery boy for a busy neighborhood butcher. He never stopped working after that. Though he wasn’t old enough to shave yet, he was the man of the family now.

He stayed in school for the next few years, but he was never without two or three part-time jobs. Curb painter. Paper and grocery boy. Caddie at the Forest Park Golf Course on Woodhaven Boulevard, the first-known Trump-family connection to the potentially lucrative world of golf. Six decades later, when I needed a lift to that very same public course, my grandfather drove me there in his brand-new, dark blue Cadillac—he bought a new one every three years—and proudly pointed out the precise location of the old caddie shack.

It was right over there, he said. But some of the players were stingy tippers.

He could still remember which ones.

And he hung around long enough to hit a few balls. That’s how it’s done, he deadpanned. Do you need a ride home?

Throughout his early teens, he worked for pay before and after his classes, not to mention every weekend, and diligently brought his modest earnings home. Which his widowed mother no doubt appreciated. At age fifteen, the fatherless boy had what certainly seems in hindsight like a life-changing revelation. Instead of working for other people, couldn’t he earn more money by starting a business of his own? His timing could not have been better. The Great War was over. The veterans who’d made it through the conflict were establishing new lives back home. The docks and factories and retail establishments of New