If biography is destiny, that helps explain why Hillary Clinton and Donald Trump are among the most dissimilar presidential candidates ever to face off on Election Day.
Rarely has ambition, in such different forms, taken such different routes toward the White House.
Here, for each candidate, are five defining moments that occurred before most Americans got to know them — Clinton before the White House and the State Department, Trump before Atlantic City and The Apprentice.
Donald J. Trump (b. June 14, 1946)
By the time he was 13, Donald Trump was “a pretty rough fellow,’’ his father, Fred, once admitted. The boy was variously described as bullying, rambunctious and rebellious. “I always loved to fight,’’ he told biographer Michael D’Antonio. He said he gave a teacher in elementary school a black eye.
So, in 1959, Trump was enrolled in the New York Military Academy, a boarding school in the Hudson Valley that was both strict (students wore uniforms) and lax (hazing was common).
Trump told D’Antonio that when he sassed one instructor — a World War II vet — he got roughed up. “It was not like what happens today,’’ he recalled. “You had to learn to survive.’’
Trump thrived. And in this presidential campaign, when his Vietnam War deferments and military experience became an issue, he cited high school as his military experience. It gave him, he said, “more training militarily than a lot of guys that go into the military.’’
Fred Trump was a big New York developer and landlord. In 1962 he bought Swifton Village, a mostly vacant apartment complex in Cincinnati at a foreclosure auction for $5.7 million.
Donald, a college student, would later write in The Art of the Deal that he spotted the opportunity himself: “While my friends were reading the comics and the sports pages, I was reading the listings of FHA foreclosures." The Trumps spent $500,000 to upgrade the complex, and within a few years the vacancy rate was near zero.
Donald spent time on site; how much is in dispute. In a letter to the Cincinnati Enquirer in 2003, he said that he “lived in Cincinnati and worked in the complex for two summers, fixing it both physically and financially …’’
But a longtime Swifton Village maintenance man told the newspaper in 1990 that Donald would fly in and stay for only a few days at a time, helping with tasks such as landscaping. A Trump biographer, Gwenda Blair, says the project was far more Fred’s than Donald’s.
The Trumps sold in 1972 for $6.75 million, at “a tremendous profit,’’ Donald said. In his book, he called it his first multimillion-dollar deal.
Art of the deal, Act I
By the mid-1970s the once-elegant Commodore Hotel next to Grand Central Terminal was a failing business in a nearly bankrupt city.
But Donald Trump saw a solid building in a peerless location in a world city on the rebound. He obtained an option to buy the hotel from a bankruptcy trustee; interested Hyatt Hotels in operating it; used political connections to help secure generous tax breaks (the first ever given a commercial project in New York); persuaded banks to loan money and his father to put up the rest.
Then the real work began — shoring up the building’s structure, constructing a new lobby and sheathing the façade in glass. The cost ballooned by tens of millions, but the Grand Hyatt was a success from the day it opened in 1980.
Fred Trump's real estate empire was in unfashionable areas of Brooklyn and Queens. Now Donald had made in Manhattan. And he had set the stage for his most ambitious construction project: Trump Tower.
Springtime is for losers
The United States Football League was founded on the idea that Americans were so crazy about pro football they’d even watch it in the spring.
The league’s first year, 1983, was fairly successful. But Trump, owner of the New Jersey Generals, pushed a different idea: If God wanted football in the spring, he wouldn't have created baseball.
Trump wanted to play in the fall, head to head with the NFL. Some USFL owners doubted they could prevail against the mighty NFL. But others, desperate over big losses from bidding wars with the NFL for players (which Trump fueled), backed Trump.
Before the 1985 spring season, the league announced that the 1986 season would be played in the fall. Then it filed a $1.32 billion anti-trust suit, claiming the NFL was freezing the USFL out of TV contracts and stadiums. The real goal: force a merger.
The trial resulted in a jury verdict for the USFL — and damages of $3. Trump, the only USFL owner the league’s lawyer (handpicked by Trump) put on the stand, was an unsympathetic witness. It seemed less like big guy vs. little guy than fat cat vs. fat cat.
Less than a week later, the USFL suspended the fall season. It never played another game.
For Trump, however, the USFL was another step toward national celebrity. And it proved his willingness to take on established interests, be it the NFL or the GOP.
Central Park’s Wollman skating rink was closed by the city in 1980 for a three-year renovation. In 1986, it was still closed.
Enter Trump. He offered to fix, quickly and cheaply, what he called “the greatest embarrassment’’ of Mayor Ed Koch’s administration. Koch agreed.
Unbound by rules and restrictions that governed the city, Trump finished the job in three months for less than $2 million, about $750,000 under budget. (The contractor, eager for future Trump work, did the job at cost.)
For Trump, the real payoff was publicity. He staged a reopening ceremony with skating stars such as Peggy Fleming and the ice dancing team Torvill and Dean that was unlike any “in the history of ice skating,’’ he told a biographer, Timothy O’Brien. “There are moments in life that are so good, you can never duplicate them.’’
Trump had showed that a businessman — him in particular — could succeed where politicians and public officials had failed.
Hillary Rodham Clinton (b. Oct. 26, 1947)
Sometime in 1961, excited about the America’s race to the moon, Hillary Rodham wrote to NASA expressing interest in becoming an astronaut. Sorry, the space agency replied: Astronauts had to be male.
The story fits the narrative of Hillary as a life-long gender pioneer, and she has told it for years. But some people, not all Clinton haters, are skeptical that NASA — famously obsessed with PR — would deliver so categorical a rebuff.
No copy of the letter has been found, and there’s no evidence NASA routinely replied to such queries with such candor. But in September 1961, the agency quietly terminated a program to screen potential female astronauts for the risky missions (possibly because the military didn’t allow women to fly in combat).
After studying the issue in depth, The Washington Post concluded earlier this year that there’s no reason to disbelieve Clinton’s story.
No student ever spoke at a Wellesley College graduation until 1969, when, by senior class demand, student body president Hillary Rodham took the stage.
It had been a tumultuous period, with the murders of Martin Luther King and Robert Kennedy the year before and the ongoing trauma of the Vietnam War. Ruth Adams, Wellesley’s starchy president, was against a student speaker. After learning it would be Rodham, she relented.
Although the graduate had worked all night on her speech, she focused on the remarks of the commencement speaker, Edward Brooke, a moderate Republican and the only African-American in the U.S. Senate. Brooke didn’t mention King, Kennedy or the war. He expressed “empathy’’ with demonstrators’ goals while rejecting “coercive protest.’’
“The problem with empathy,’’ Rodham countered, “is it doesn’t do us anything. … Our leaders have used politics as the art of the possible. And the challenge now is to practice politics as the art of making what appears to be impossible possible.’’
Emotional, electrifying and at times incoherent, Clinton’s speech captured a moment when, as she put it, “we’re searching for more immediate, ecstatic and penetrating modes of living.’’
Some parents and administrators were aghast, but Rodham’s classmates gave her a seven- minute standing ovation. The next week LIFE magazine ran excerpts from the speech and a photo of the speaker.
As Hillary Clinton wrote in her autobiography, Living History, ”The accolades and the attacks turned out to be a preview of things to come.’’
In 1971, during her second year at Yale Law School, Rodham accepted a summer job with a left-wing firm in Oakland. Bill Clinton, her fellow student and boyfriend of several months, had been offered a summer job organizing in the South for George McGovern’s fledgling presidential campaign.
But he surprised her by saying he was turning down McGovern to go west with her. “I tried to let the news sink in,’’ she recalled in Living History. “I was thrilled.’’
‘“Why,’’ I asked, “do you want to give up the opportunity to do something you love to follow me to California?’’’
‘“For someone I love, that’s why,’’ he replied.’"
She would make many professional and personal compromises over the years for him; that summer he accommodated her. When they returned to New Haven that fall, they moved in together. Four years later they’d enter into one of the most epochal of political marriages.
Health care reform, Act I
In 1979, the new governor of Arkansas tapped his wife to lead a new Rural Health Advisory Committee, even though she admittedly knew little about health care or rural areas.
The issue was a minefield; country doctors already had rebelled against attempts to expand medical care by using non-physicians.
Hillary Rodham (still using her maiden name) solved the problem partly by using her connections to tap federal funds for a series of health clinics in the state’s poorest counties. She was so successful that Clinton subsequently appointed her to head a similar effort to improve education in the state.
The Clintons have touted the education effort ever since. But the health panel was an earlier sign that she’d be her husband’s partner not just in politics but in governing, and that she’d have the health care portfolio.
In her autobiography, Hillary wrote that her Arkansas experience “made me excited and hopeful’’ when President Clinton named her to chair his health policy reform initiative in 1993.
But Washington was different, and she failed. “I didn’t fully realize the magnitude of what we were undertaking. My work in Arkansas … didn’t rival the scale of health care reform.’’
In Sam’s Club
All 15 Walmart corporate directors were men. By 1986, that had become an embarrassment to the founding Walton family. So Sam Walton turned to a woman who was not only the first female partner at Little Rock’s powerhouse Rose Law Firm, but the governor’s wife.
On the giant retailer’s board, Hillary Rodham Clinton (she’d added the last name in deference to Southern sensibilities) picked her spots. She fought for causes close to her heart (equal opportunity for women and environmentally responsible business practices). And she let some issues slide, notably Walmart’s hostility to unions.
After she’d left the board and Walmart came under increasing criticism from liberals, she rarely discussed her trailblazing role at the company — an illustration of her penchant for downplaying potentially controversial or unflattering history.
In 2005, a Walmart political action committee gave Clinton’s Senate campaign $5,000. After an internal memo surfaced that discussed holding insurance costs down by discouraging people with health problems from working for the company, she gave it back.