The business is, yes, about putting up buildings, but it’s also about dealing with these people. It’s about being friendly with politicians. It’s about having them respect you. It’s about having them like you.
—DONALD TRUMP
As a place of dreams, Fred Trump’s office left much to be desired. Formerly occupied by a dentist, it was decorated with kitschy cigar-store Indians and furnished with battered desks, filing cabinets, and chairs. The cramped space felt even more claustrophobic from the addition of a cheap dropped ceiling and fluorescent lights that cast a bluish tinge on everything. The walls were filled with the businessman’s version of a hunter’s trophies—framed plaques and certificates—but otherwise the place was devoid of any human touches, except for the small collection of patriotic bric-a-brac, which included a statue of an eagle, wings spread, grasping a stars-and-stripes shield in its talons.
Coldly functional as it may have been, the Trump office was a haven from the surrounding neighborhood. Two blocks to the west, a sprawling subway yard complete with a twenty-four-hour repair shop occupied seventy-five acres crisscrossed by tracks. Immediately to the east, Coney Island Hospital welcomed a steady stream of ambulances, sirens blaring, day and night. To the south the elevated Belt Parkway, humming with traffic, cast a shadow and a cloud of exhaust fumes on the streets below. Known as Gravesend, the neighborhood was rarely in the news, except for the occasional murder or when, in 1970, the mayor announced a massive sewage-treatment plant would be built on the eastern end of Avenue Z.
Given the setting, young Donald Trump could be forgiven for letting his mind wander to Manhattan. Keenly aware of the value locked up in his father’s eighty-or-so buildings, which were worth well over $100 million, Donald urged him to refinance and create a pool of cash for new endeavors. Fred believed in Donald’s ability, considered him a natural successor, and was willing to use his equity to back his son’s ideas. However, Fred was extremely wary of doing business in Manhattan, which was one of the most expensive places in the world for developers, and a locale where his friends from the Brooklyn Democratic clubhouses might run up against the limits of their powers.
Never truly comfortable as a public man, Fred had stopped pressing for media attention after his run-in with the US Senate banking committee. His instinct was confirmed on the rare occasions when he had contact with the men who operated at City Hall in Manhattan. When Fred attended a fund-raising luncheon for the reelection campaign of Mayor Robert F. Wagner, a Democrat, Fred’s pledge of $2,500 wound up in the newspapers as Republicans assailed Wagner for taking money from people doing business with the city. (Wagner gave the donation back.) The fund-raiser had been organized by a politically powerful lawyer named Abraham Lindenbaum, who sat on the city’s Planning Commission. Many New York real estate men, including William Zeckendorf, used Lindenbaum’s firm. Fred Trump had engaged him for Trump Village, which was built under the Mitchell-Lama law. Lindenbaum and his partner Matthew Tosti submitted a ninety-nine-page bill for forty-five hundred hours in court appearances, to be paid out of public funds, even though the job they claimed to have done was actually handled by a city agency and another contractor. The invoice found its way into the local papers, where it became a scandal.1
Although Fred Trump was not accused of breaking the law in the Lindenbaum affair, he was required to testify before the New York State Commission of Investigation, which had been established in the 1950s to curb political corruption. In a setting less congenial than when he was questioned by the Senate banking committee, Fred had to contend with hours of questions about his state-subsidized Trump Village development. Much of what he said revealed an almost dazzling level of manipulation. For example, after first claiming ignorance, Trump consulted his lawyer and changed his testimony to explain how he had created an independent company to buy used equipment—backhoes, trucks, etc.—which was then leased to the Trump Village project at rates as much as twenty times their actual cost. (A truck valued at $2,600 rented for $21,000. Two tile-scraping machines valued at $500 apiece netted Trump $8,200.) Since Trump’s fee as the builder was based on the ultimate final cost of construction, like a commission, he earned money once by renting the equipment at exorbitant rates and again when he got his final fee for developing the apartment complex.
Clever in the extreme, Trump’s equipment scheme was technically legal under the rules of Mitchell-Lama, and he was plainly irritated by the probing questions of the commission’s lawyers. “I’ve got forty-three corporations I’m sole stockholder in,” he explained. “These things escape my mind sometimes.”
Trump was advised, as he testified, by the same Matthew Tosti whose name appeared on the contested ninety-nine-page bill. At some points Tosti sought to answer questions for his client and was admonished to let the witness speak for himself. The commission established that Trump had deliberately inflated estimates for the cost of construction and used excess subsidized funds to build a shopping center near the apartments. Other witnesses explained how he had received $500,000 in extra profits by exploiting certain provisions in the law. Finally, the director of a large, well-established nonprofit housing group testified that his organization had been authorized to build on the Trump Village site in 1957, but had run into a political trouble.
“We were told by members of the Board of Estimate that we couldn’t get approval until we compromised with Mr. Trump,” said Abraham Kazan of the United Housing Federation. “So we gave up more than half … and the Board of Estimate finally approved the amended plan in May 1960.”2
Like the Eisenhower-administration investigators who probed the Federal Housing Administration, New York State’s investigating commission revealed a program that seemed to be purposely designed to benefit builders guided by skillful lawyers. During the state hearings, the very same Senator MacNeil Mitchell who helped create Mitchell-Lama was required to answer for more than $400,000 in fees his law firm received from builders—including Fred Trump—who participated in the program. Once again a witness noted that his unseemly gain was perfectly legal and expressed a bit of outrage over the suggestion that anything improper occurred. Mitchell even described the work he had performed for builders as “a public service” and gave himself credit for not being one of many public officials who actually took cash from builders in exchange for their influence. He had actually worked for the money.3
No one was prosecuted as a result of the commission hearings, but the editorial page of The New York Times mentioned Fred Trump by name as it lambasted those it termed “profiteers” who had taken advantage of the taxpayers. The head of the commission criticized Trump and others as “grasping and greedy individuals” whose manipulations exploited the citizens of New York, drove up rents, and violated the spirit of Mitchell-Lama, which was supposed to create affordable housing with a combination of tax breaks and subsidized financing.4
Although he got to keep his profits and would reap the rents from both Trump Village and the shopping center for years to come, Fred Trump was bruised by his experience before the commission. Nothing in state or federal law would prohibit him from filing new applications to receive the tax breaks and subsidies that government programs offered. But the scent of scandal that had attached to him during the commission hearings would make it much harder for him to win approval. Competitors and enemies—every businessman has them—would surely use his record to oppose any new Trump applications in hopes of thwarting a rival or of boosting their own prospects for handouts.
Then there was the whole matter of politics. Though a Republican, the practical Trump had aligned himself with machine Democrats, who were subject to increasing scrutiny by good-government types. Weeks before Trump testified, Tammany’s Mayor Wagner had been defeated at the polls by reform-minded Republican John V. Lindsay, whose campaign motto, borrowed from writer Murray Kempton, had been “He is fresh and everyone else is tired.” During Lindsay’s eight-year reign, the Lindenbaums, Mitchells, and others who had long wielded so much influence on behalf of builders would be sidelined. Any Trump plan that would require city approvals, and every big housing project required city approvals, would have to win the Lindsay administration’s favor on its merits. Having never done business under such circumstances, Trump began to focus more on the task of training a successor.
In a family that honored male privilege, Fred Trump Jr. was first in line to take control of the business. Eight years older than Donald, Freddy had tried to become the killer king of his father’s imagination but was too softhearted to succeed. He spent his high school years at a genteel Episcopal day school on Long Island instead of at a military academy. At Lehigh University he joined the Air Force Reserve Officers Training School and thought about becoming a pilot, but when he completed his studies, he dutifully began work as his father’s assistant.
In the offices on Avenue Z and during their time in the field, Freddy Trump had trouble taking in the lessons his father tried to teach him. An enormously wealthy man who nevertheless picked up nails at his building sites, Fred Trump couldn’t stand even a penny of waste. Somehow his eldest son missed the emphasis his father placed on thrift. Given the chance to renovate an old building, Freddy installed brand-new windows. His father berated him when he found out because he thought the old ones would have served well enough for a few more years.
As Donald watched his elder brother try to please their father, he felt sympathy for him. Freddy had been a kind and concerned sibling who lectured Donald on the dangers of smoking and drinking, two habits Freddy couldn’t break. But as much as he loved his brother, Donald couldn’t help but feel a bit exasperated by Freddy’s problems. Their father and mother never drank to excess and probably considered such behavior a sign of bad character. (Fred Sr.’s own father may have been an alcoholic.) Donald wished Freddy would have tried harder to show them he could control himself. Also, Trump men were supposed to be tough, even when dealing with each other, but when his father lashed out at Freddy, he was so hurt he seemed to physically shrink. It was hard to watch.
Learning from what he saw, Donald resolved to stand up to anyone who challenged him, including his father. Years later he would say, “I used to fight back all the time. My father was one tough son of a gun.” However, he added, “My father respects me because I stood up to him.”
As Donald began working full-time in the family business, Freddy was assigned the daunting task of shepherding a proposed development on the site of the last big amusement park in Coney Island. Steeplechase Park had opened in 1897 on fifteen acres of seaside real estate. Founder George Tilyou had gone into the amusement business after getting bored with real estate. He developed a midway of games and concessions and decorated the place with the image of a demonically grinning character called either Tillie or Steeplechase Jack whose hair formed devil’s horns and whose face surely hovered in many a child’s nightmares. The park’s main attraction was a mechanical “horse race” that allowed a dozen riders—mounted two per steed—to ride along tracks that encircled the entire lot. Attendants wore silks and a bugler announced the start of each race with the famous “Call to Post” tune. Racers cleared several hurdles and crossed a stream, getting sprayed with water. When they finished the ride, they were subject to a gauntlet of harassing clowns and “blowholes” that lifted women’s skirts and prompted cheers from a crowd of people who were seated on a small set of risers.
Over the years millions of people had been entertained at Steeplechase Park, where Tilyou’s parachute-jump attraction, and its 250-foot-high tower, became a landmark. Steeplechase thrived despite the rise of the bigger Luna Park, which was anchored by a ride in which thirty occupants of a winged “ornithopter” traveled to a papier-mâché moonscape where they were greeted by moon maidens. Together these amusement centers created a Coney Island mystique that made the gritty stretch of seaside an object of nostalgia even for people who had never been there. (Part of this phenomenon was due to Coney Island’s many appearances in books, movies, and songs.) By the time Fred Trump bought the Steeplechase property, Coney Island’s peak as a day trippers’ resort had passed. Many of the middle-class Brooklynites who once flocked to the sands had left for suburbia. With business dropping off, honky-tonk joints closed. Properties were sold and apartment buildings began to sprout just off the boardwalk. George Tilyou’s heirs sold the 12.5-acre Steeplechase Park to Fred for $2.5 million. Trump envisioned high-rise apartment buildings of the sort he had seen during vacations in Miami Beach.
Although apartments were being built in Coney Island, none were located in the blocks south of Surf Avenue where the amusement parks had operated and which city officials had reserved for recreational facilities. In this area, almost all the properties offered direct and unrestricted access to the beach, which poor and middle-class New Yorkers had come to view as their own. Over the generations the freely accessible Coney Island beach had become a symbol of egalitarian New York, one of its few amenities that didn’t require one to purchase an admission ticket. As one local business advocate said, the city desperately required a “place where the low man on the totem pole can come and blow his top.” For his part, Freddy Trump argued that Coney Island’s days as a resort for even the low man had long since passed. “You and I wouldn’t take our kids there,” he argued. “People are afraid to walk on Surf Avenue at night.”
Unfortunately for Freddy, the Steeplechase project became ever more difficult as time passed. The dashing Mayor Lindsay’s Election Day defeat of an old-fashioned, cigar-chomping challenger named Abe Beame greatly diminished the power of the machine politicians who had made things easier for Fred Sr. Then there was Freddy’s father’s troublesome appearance before the investigations commission. No matter the outcome, the Trumps’ prospects for overcoming the city’s restrictions on the Coney Island property had dimmed as the grilling made Fred Sr. seem part of the corrupt Tammany past. He tried to induce Walt Disney and others to operate Steeplechase Park as an amusement center, but no one took him up on the offer. In the summer of 1966 he proposed dropping his plan in favor of a bigger development that would include housing and a year-round amusement and convention center enclosed by a glass or plastic dome. These facilities would be built on property that would have to be acquired by the city and cleared of businesses that were open and operating.
Sketched by Morris Lapidus, the “pleasure dome,” as The New York Times called it, would be tall enough to house a Ferris wheel. In the drawings its swooping lines echoed Eero Saarinen’s iconic new terminal at Dulles International Airport in Washington, D.C., which had opened in 1962. Of course an architectural drawing can be had quite cheaply, and the plan, which was presented at the Lapidus-designed Americana Hotel in Manhattan, wasn’t much more than a vague vision of something that might occur under ideal circumstances. Lapidus even suggested that the recreation area be funded and operated by some new government agency, created for this sole purpose, which would also compensate the business owners displaced by the new development.
One voice raised in favor of Trump’s grand vision for Coney Island belonged to Brooklyn borough president Abe Stark, whose local claim to fame began with a billboard for his tailoring business that made the promise HIT SIGN, WIN SUIT, posted beneath the scoreboard at Ebbets Field, which had recently been demolished. Seen by fans at the ballpark, in news photos, and in newsreels, the sign had made Stark so well-known that the voters promoted him from tailor, to city councilman, to borough president. However, Stark was not a natural politician and never gained the type of political power enjoyed by his predecessor (and Trump supporter) John “Cashbox” Cashmore. Stark was unable to rally even his fellow businessmen to support the Trump/Lapidus plan. The Coney Island Chamber of Commerce actively opposed the idea and issued a scathing statement, which said in part, “Mr. Trump is stuck with the present Steeplechase property on which he cannot build housing because of the zoning. Under the plan he would exchange it for the city land. He’s getting rid of a lemon.… The beach would become a personal haven for people who lease apartments from Mr. Trump.”
Organized by Fred Jr., the Americana Hotel press conference yielded nothing more than a bit of publicity that promoted Fred Trump Sr. as a visionary. Weeks later Freddy invited his father’s friends and associates to a wrecking party inside the huge glass-and-steel Pavilion of Fun, which once housed rides and attractions, which had since been sold to amusement operators across the country. (The park’s towering parachute jump remained because the estimated cost of dismantling it and shipping it to a new locale discouraged would-be buyers.)
Although he was still stymied by city zoning regulations, Fred Trump Sr. acted as if he had already overcome his problems with the city. As guests sipped on champagne, six young women in bikinis and hard hats appeared to pull on ropes that toppled small pieces of a brick wall. The “girls,” as the papers described them, then stood in the bucket of a giant earthmover and posed for photos. Fred took a turn in the operator’s seat of a bulldozer. Onlookers then got the chance to hurl bricks at a section of pavilion glass where a huge painting of Steeplechase Jack had decorated the panes and welcomed visitors for more than fifty years.
The last publicity stunt of Fred Trump’s career, the bikini/payloader/champagne extravaganza was a good example of a phenomenon that historian Daniel J. Boorstin had recently described in a landmark book called The Image: A Guide to Pseudo-Events in America. Boorstin was deeply concerned about how moral ideals, genuine relationships, and human experience were being replaced by images and “pseudo-events” that were manufactured by public relations experts, corporations, politicians, and governments. Americans, who were awash in these images and events, often accepted them as real and meaningful. One sign of this acceptance was the way people began creating more and more of their own posed photographs and staged home movies. These could then be compared with the images of famous people who were valued as “celebrities” and the concepts of the good life presented by advertisements for whatever was “new” and “modern.” Of course advertising only succeeded when people bought a product, and this way the novelty was destroyed. Status seekers were thus frustrated until they acquired the next new thing to be advertised and sold.
The problems Boorstin described would occupy generations of future writers. Many sought to address the anxiety and ennui that were symptoms of what he called a “disease of extravagant expectations” caused by imagery and pseudo-events. Susan Sontag would observe in On Photography that inexpensive photos, produced by the hundreds, created a record that allowed an unprecedented level of self-examination—she called it “self surveillance”—that discouraged spontaneous human expression and encouraged posing and playacting. People were generally too busy to devote much time to considering how they were affected by the media bombardment and simply absorbed it or reacted as best they could.
Aside from their occasional complaints about the pressure to “keep up with the Joneses,” most people were actually quite occupied with keeping up. Every day brought more images and pseudo-events that insisted that striving for the right possessions—a new suit, car, house—would bring fulfillment and even happiness. That few people ever reached this state, as defined by the manufacturers of this reality and illustrated on TV, was hardly ever mentioned, even in private, because to do so would cast doubt on the whole basis of commercial life.
In the accelerated marketplace that Boorstin and others described, a small number of energetic, talented, and resourceful men could achieve the high-status life depicted in the imagery that surrounded them. This was most true for those who, like Donald Trump, might enjoy the advantages of talent, family wealth, and useful connections inherited from a successful father. When still a student at the University of Pennsylvania, Donald was so confident in his future that he couldn’t wait to begin life as his father’s partner and fulfill the older man’s dream for him. “My father was a businessperson that expected tremendous success out of me,” he would eventually recall.
A month after the demolition celebration on Coney Island, Fred Trump appeared before the city’s Planning Commission, which was leaning against the development scheme and toward the public purchase of the Steeplechase land for use as a park. Trump told the panel they were wasting “a valuable piece of property” because people would visit only in the summer. However, he didn’t fight hard to save his project, and any pain he may have felt over the loss of the land was surely eased by the $1.2 million profit he made when the city paid him for the site.5
Although his gain of roughly 25 percent per year was more than triple the rate of growth in the Dow Jones Industrial Average for the same period, Fred Trump’s profit on the Steeplechase property was much less than what he would have reaped from his original plan. He had envisioned a river of rent payments from apartments and businesses that would eventually pay off his financiers and yield millions of dollars in net revenues even as inflation drove up the value of the property. This formula—investment + time = revenue and higher value—was the magic of real estate. By following it, Fred Trump had amassed assets that allowed him to develop ever bigger projects while simultaneously reducing the risk to his personal fortune. Eventually these methods allow developers to use the equity in one project as a down payment on another and escape using any of their own cash. They could even avoid paying taxes on their profits by investing them in a new property. This provision of the tax code, originally written to aid farmers, made real estate an even better business.
The Trump variation on the basic real estate recipe often included a dollop of political grease and a little show-business spice, for the sake of publicity. The precise mixture depended on the location, the competition, and the level of public interest. A celebrated architect, for example, could win invaluable publicity for a planned development and encourage city officials to regard it as beneficial, and even prestigious. Good press could influence those who might buy or rent at a certain location. The Steeplechase project all but required Morris Lapidus and bathing beauties in the bucket of a payloader. But as Fred Trump offered flutes of champagne and invited his guests to smash Jack’s face, he showed that his feel for New York in general, and Coney Island in particular, was just a little bit off.
A proper pseudo-event to bid farewell to the old amusement park would have been a glass-of-beer occasion. Instead of being invited to hurl bricks at an emblem of the good ol’ days, the invitees could have been offered a chance to flutter to the ground from the top of the parachute jump. What was being lost deserved to be recognized with a bit of respect. Instead, the event conflated Trump’s desire for profit and the city’s own needs. This approach ignored the value of an ocean beach that could be accessed by millions of people for the price of a subway token. And Trump’s complaint about how the beachfront property would be wasted on a recreation area that received just two months of use ignored the many locals and tourists who walked the beach, gazed at sunsets, and cast for striped bass in the cooler months. This was the Coney Island they would lose to development, and it was the one they gained as the city denied Trump the zoning changes he needed to proceed.
Fred Trump Jr., who was supposed to help see the project through to completion, fled the family business after the Steeplechase proposal was killed. When TWA accepted his application, he began training for a career as a pilot, which he would pursue for many years. At the time TWA had retired the last of its prop planes in favor of an all-jet fleet. First-year pilots were paid the 2015 equivalent of $110,000 per year, and the most senior ones earned more than three times as much.
Glamorized in the media and respected by the public, pilots enjoyed high social status. Donald Trump would remember that his brother’s work, and family life in Florida, made him happier than Donald had ever seen him. However, a happy life was not enough for a Trump man. The model of masculinity established by Fred Sr., which he surely inherited from his German immigrant father, called for extreme competitiveness and victories that yielded great wealth. Pilots were well compensated, but they were not rich by Trump standards. And given that the job mainly required the safe transit of an airplane and its passengers, how could one pilot prevail over another? He could not, which was why Fred Sr. and Donald couldn’t help but torment Freddy when they were together. “What’s the difference,” asked Donald, “between what you do and driving a bus?”6
* * *
With his eldest son striking out on his own and his dream project defeated, Fred Trump Sr. reached a turning point. At sixty-one he had lived twelve years longer than his own father, and he had, in less than three decades, built one of the largest real estate portfolios in New York City. But the game that he knew was changing. Old friends in politics and government were being squeezed out or leaving of their own accord. The city government was facing serious problems as budget deficits begun under Wagner continued with Mayor Lindsay. The middle-class workers and families who had once eagerly filled Trump’s buildings in Brooklyn were joining the “white flight” to the suburbs. The neighborhoods they left were tumbling into poverty.
New York was hardly alone in this crisis. Much of urban America had begun a slow but steady decline in the 1950s. This accelerated in the 1960s and was accented by race riots that saw mostly white police forces battling black citizens. In 1964, thousands of black residents took to the streets in Harlem and other New York neighborhoods after a white off-duty officer shot a black teenager. In 1965, long-simmering racial animosity led to widespread rioting in the Watts neighborhood of Los Angeles, and in the following two summers riots occurred in Cleveland, Omaha, Newark, and Detroit. Bad as things were by ’67, they got worse in 1968 after Martin Luther King Jr. was killed at the Lorraine Motel in Memphis, Tennessee. Fifty cities erupted in violence that summer. Police in Baltimore and Chicago were so overwhelmed that National Guard troops were called to patrol the streets.
The effects of the racial unrest of the 1960s were long lasting as urban centers lost businesses, jobs, and people. In the 1970s New York would suffer a 10 percent decline in population, the first time in its history that the city had endured a double-digit drop. Many businesses closed, and major employers, including manufacturing companies, moved to the suburbs and the Sunbelt, taking jobs with them. Other cities suffered similarly. In 1971 more than two hundred people were killed in race-related riots from Boston to Los Angeles. Cities suffered billions of dollars’ worth of damage, and property values declined as arsonists burned individual buildings and entire blocks.
Although race was the most evident factor in both white flight and the civil unrest, poverty also loomed large. Discrimination in jobs, housing, and education hobbled minority Americans who sought any level of wealth and security. In the outer boroughs of New York City poor black and Hispanic newcomers moved into neighborhoods that were vacated by whites and their employers. Many of these communities became official “poverty zones” where 30 percent or more of the residents depended on government welfare payments. This problem was especially acute in the Flatbush, Greenpoint, and Coney Island areas of Brooklyn, where incomes fell and crime rates rose.7
Confronted with downward pressure on rents and declining property values, homeowners, real estate investors, and landlords in certain New York neighborhoods faced the worst market conditions since the Great Depression. More than one hundred buildings per month were being abandoned, and in most cases tenants who found themselves without utilities and maintenance quickly departed. Squatters and scavengers would eventually be followed by city demolition crews. In this way, crime was followed by blight and entire blocks were devastated.
Some owners resisted selling their buildings to blacks or Hispanics who made inquiries, and some landlords refused to rent to them. Although a number of the landlords were genuinely racist, most would say they were motivated by financial concerns. They equated black and brown with poor and feared unpaid rents and the expense of eviction battles. Developers in New York’s outer boroughs cut back their activities, especially in middle-class and poorer neighborhoods, and hoped that with time they might once again make real profits building homes and commercial space. By 1969 private developers had stopped building market-rate residences for all but the wealthiest New Yorkers (The Times described them as the top “7 percent”), and the only apartments being developed for the rest of the population were those subsidized by the government. These were going up at such a minimal rate that waiting lists were decades long.8
On Avenue Z, Fred Trump hunkered down, contenting himself with collecting rents and controlling costs on the thousands of apartments in buildings he owned and operated. With Freddy’s departure from the business, Fred also focused on training his son Donald, who was spending his weekdays at the University of Pennsylvania and his weekends in New York in the family business. At Penn, where he enrolled after two years at Fordham, Donald studied real estate at the Wharton School of Finance and Commerce. A decade earlier, editors at Penn’s student newspaper had decried the Wharton School’s influence on campus, describing it as “the first and most important destructive influence” on the study of science and liberal arts. In his time on the campus Donald Trump absorbed all he could from his professors, devoting special attention to the intricacies of high finance. At home in New York he studied his father’s holdings to see where he might find opportunities for growth.9
Visiting various buildings with his father, Donald learned the mundane art of rent collecting, which, when done in person, required a step to the side whenever a door was opened just in case someone was armed with, say, a bucket of hot water. Such things did occur. Donald was also educated in the various ways that proper maintenance would extend the life of certain equipment and fixtures while preventing costly emergency repairs. Following his father’s example, Donald never went to work without a jacket and tie, and he made certain that he understood enough about every aspect of the business to instruct employees and follow up on the tasks he assigned to them.
Given his choice, Donald would have preferred to forgo his formal education. He was not a natural student and wasn’t much interested in the social opportunities available to him on or off the campus in Philadelphia. However his father insisted that Donald earn a degree. (It was a point of honor for him that his son was an Ivy League man.) If Donald had dropped out, he would have lost his student deferment and been subject to the military draft and, perhaps, combat duty in Vietnam.
As the war had dragged on, Trump’s generation of young men had joined the armed services at a rate of more than 1 million per year. More than one-third would serve in Southeast Asia. With the American military death toll climbing toward its eventual total of nearly sixty thousand, opposition to the war also increased, and public rallies were organized at campuses from coast to coast. In some places colleges and universities were shut down by protesters. Students blocked streets with barricades and set fire to draft cards and, in a few cases, campus buildings. The worst would come in 1970 when four students were killed and nine were wounded as National Guard troops fired on demonstrators at Kent State in Ohio. Followed by hundreds of protests across the country, the Kent State killings galvanized opposition to the war among the young.
Although Ivy League schools such as Columbia and Harvard were hotbeds of activism, students at the University of Pennsylvania were not so restive. However, in 1965 more than a thousand students attended an antiwar “teach-in,” and in 1967 about fifty students added black bands to their straw hats and covered their faces with gas masks during the traditional, springtime Hey Day festivities, which included parading, drinking, and picnicking. In 1968, Donald Trump’s last year at Penn, a small group occupied a building and drove away recruiters for the Central Intelligence Agency and Dow Chemical, a manufacturer of napalm, which was being used to set vast swaths of the Vietnamese countryside ablaze.
Donald Trump did not join in the protests, sign petitions, or otherwise agitate against the power of the “establishment.” Although he personally opposed the war, Trump would later say he was so intently focused on his future in business that he was not even aware of the campus protests. In light of Trump’s political disengagement, you might conclude that he was more like a college man of the fifties than the sixties. But he showed no more enthusiasm for the old-fashioned version of college life than he did for the psychedelic style of his own generation. Assiduously sober, he didn’t care for beer bashes at fraternities or druggy house parties. He generally stayed in after classes, watched the talk-show host Johnny Carson, whom he greatly admired, and went to sleep. This was his routine until he received his diploma and went home to New York. He would often say he graduated at the top of his class, but as the school does not issue official rankings, this claim cannot be confirmed or contested.
After Donald returned to New York for good, protests roiled the Democratic Party’s National Convention in Chicago, and the number of American troops in Vietnam peaked at 541,000. Thousands of young men who were no longer excused from service as students fled to Canada to escape the draft. Like others who received their diplomas and left school in the spring of 1968, Trump’s 2-S student deferment expired as of July 1968. For two months he was classified 1-A and ready for conscription, but when he reported for a military physical in September 1968, he was found medically unfit. His new classification, 1-Y, permitted him to be called only in case of national emergency.
Considering that roughly 60 percent of his peers also avoided wartime service, Trump’s record was not especially remarkable. Roughly 10 million men in his age group were not drafted due to deferments and special status. However, as time passed, Vietnam-era service would become an issue for a generation of political figures including Bill Clinton, Dick Cheney, and Mitt Romney, who all had to explain the deferments that permitted them to escape the draft. When asked about his war years experience, Trump would often point to a lottery system begun in December 1969, which assigned men draft priority based on a random drawing of birth dates and gave him number 356. No one with a number higher than 195 was ever called to serve.
“I actually got lucky because I had a very high draft number,” he would tell a TV interviewer in 2011. “I’ll never forget, that was an amazing period of time in my life.” In fact the lottery was not a factor in his experience. It didn’t occur until fourteen months after he received his medical exemption, and eighteen months after he’d left Penn. Nevertheless he would recall, “I was going to the Wharton School of Finance, and I was watching as they did the draft numbers.”
When the subject came up in conversation in 2014, he repeated the draft number story. But when offered the chance to work through the details, he seized it. Yes, he agreed, if the first lottery took place in 1969, he must have been mistaken about living in Philadelphia. And the gap between his graduation from Penn and the lottery could be explained by a medical deferment. As he talked, Trump slipped off his black loafer and pointed to his heel, where a little bulge pushed against his sock. “Heel spurs,” he explained. “On both feet.” The deformities qualified a would-be draftee for a medical deferment. Unlike others who dealt with the same question as public figures, Trump wasn’t defensive about never having served. The war “was a mistake” he said, and he was grateful to have remained a civilian.10
But Trump also insisted that he had actually known military life. In a separate conversation he said, “I always thought I was in the military.” He said that in prep school he received more military training than most actual soldiers did, and he had been required to live under the command of men such as Ted Dobias who had been real officers and soldiers. “I felt like I was in the military in a true sense,” added Trump, “because I dealt with the people.”
Probably not many other NYMA alumni would compare military school with actual military service. But the assertion was consistent with the self-image Trump often expressed. With ambition beyond measure, he would make the most of every experience and accomplishment and lay claim to excellence in almost everything he attempted. He wasn’t just a baseball player, he was one of the best in New York State. He wasn’t just a student at Penn, he was at the top of his class. That these claims can’t be confirmed doesn’t mean he is lying. He seems to genuinely believe them, and when he says something like “I always thought I was in the military,” he is sharing the truth as he feels it.
No one would contest what Trump had to say about his state of mind when he took up adult life in New York City in 1968. Time and again he has said that he had gazed at Manhattan and thought about how he would change the most famous skyline in the world. Confident in his abilities and wholeheartedly optimistic, he wasn’t hoping or dreaming. He believed—no, he knew—it was going to happen. It was just a matter of time.