The Last 30 Years: A Look Back at Trump and Hillary’s Trajectory Toward the Presidency

The Last 30 Years: A Look Back at Trump and Hillary’s Trajectory Toward the Presidency

Hillary Clinton‘s 30 years of political experience have become quite the talking point in this year’s race to the White House.

Despite Clinton’s assertion that the decades of public work make her poised for the presidency, her opponent Donald Trump has continually questioned why, then, she hasn’t already done more.

He charged of Clinton during the first presidential debate in September, “For 30 years you’ve been doing it, and now you just started thinking of solutions.”

On the contrary, Clinton has claimed that Trump has mostly spent his time since 1986 “degrading” women, according to the Washington Post.

So what, actually, have both candidates for the country’s highest office been up to?

A lot.

Here’s a side-by-side comparison of highlights from Clinton and Trump’s lives and careers for the last 30 years.


Trump: Exactly three decades before this election year, Trump had well established himself as a developer on the New York scene – and not just the heir to his father’s damaged real estate empire. Just under 10 years prior, Trump had orchestrated his first big deal in Manhattan: the building of the Grand Hyatt hotel, according to the Washington Post. In 1986, his other biggest undertaking was rebuilding Central Park’s famed Wollman ice rink, reported Forbes. Given approval by New York City’s park commissioner, Trump refurbished the rink — which, at that point, was long closed and had been the subject of multiple failed rejuvenation efforts – at no profit to himself, but raked in positive publicity. The whole project took just two months. That same year, the then-40-year-old was awarded the Ellis Island Medal of Honor among 79 other Americans. The award was meant to honor prominent citizens of foreign ancestry, reported the New York Times. Clinton: In 1986, Clinton and husband President Bill Clinton were well into his re-election campaign for Arkansas Governor. While serving as First Lady of the state, Clinton maintained her job at Rose Law Firm (which would later prove controversial), and, in 1986, was amid her tenure as chair at the Children’s Defense Fund. That year, she was approached by Sam Walton to join the board at Wal-Mart. The first female member, Clinton served as a director for the next six years, reported the Times.


Trump: In 1987, Trump first publicly identified himself as a Republican, registering for the party from the Trump Tower, according to the Post. It wouldn’t last though: as early as 2005, he told CNN, “I probably identify more as Democrat.” His return to the Republican party came in 2009. The year 1987 also marked Trump’s first toying with politics. The businessman accepted a New Hampshire Republican’s invitation to visit as part of a movement to “draft” Trump for the presidency, reported the Times. Other major moments? In May of that year, Trump met with then-Soviet leader Mikhail S. Gorbachev in regard to hotel development opportunities, the Times said. It is also the year Trump’s The Art of the Deal book was released. He’s frequently called the book his second favorite of all time – after the Bible. It was also around this time that Trump’s plan to create a “television city” on Manhattan’s Upper West Side with NBC fell through, according to the Times. Clinton: Clinton was appointed to first chair of the American Bar Association’s Commission on Women in the Profession while still First Lady of Arkansas. The organization focuses on cutting down gender bias in the legal community.


Trump: Trump acquired the famed Plaza Hotel in New York City in 1988, paying a cool $407 million. Later that year, he purchased the now-infamous Taj Mahal Casino in Atlantic City, New Jersey. The casino declared bankruptcy the next year, and after several ups and downs, closed in 2016, leaving 3,2000 people out of work, reported the National Review. This was also the year Trump established his Donald J. Trump Foundation – which is now under investigation by the New York attorney general. Clinton: Clinton took her place on the board of the Arkansas Children’s Hospital in 1988, helping usher in the state’s first-ever neonatal clinic, according to Politico. She was also recognized by the National Law Journal as one of the 100 most influential U.S. lawyers for the first time that year.


Trump: Trump’s brief role in much-maligned 1989 comedy Ghosts Can’t Do It earned him the Golden Raspberry (Razzie) award for worst supporting actor. Clinton: Clinton continued to serve as first lady of Arkansas as Bill decided to run, again, for re-election.


Trump: The businessman began to make headlines for the expensive – and dramatic – dissolution of his marriage to Ivana Trump, with whom he shares three children. Trump took his affair with Marla Maples public. In 1990, Trump also published Trump: Surviving at the Top, a follow-up to The Art of the Deal. The book’s release was not timed ideally: the Trump Taj Mahal was approaching bankruptcy, wrote the Los Angeles Times. He was missing payments to cover his debts on his properties, and the Atlantic City casino market was stalling, PEOPLE previously reported. Clinton: Clinton founded the Arkansas Single Parent Scholarship Fund, which continues to be available, today. Her husband was re-elected as governor, and she began her tenure as director on the board of LaFarge, a French concrete cement company.


Trump: The Trump Taj Mahal emerged from bankruptcy, the Times reported in Oct. 1991. In conjunction, Trump ceded 50 percent of his equity in the casino to bondholders in exchange for more time to pay off his debts. Trump got engaged to Maples. Clinton: Then-Governor Bill announced his candidacy for president on October 3. Just before, Clinton was named to the National Law Journal‘s 100 most influential U.S. lawyers, once again.


Trump: In 1992, Trump now-controversially defended boxer Mike Tyson after he was found guilty of raping an 18-year-old girl. He insisted to NBC that Tyson was “railroaded,” and called the conviction a “travesty.” “I’ve seen women going around touching him,” Trump reportedly told NBC, according to CNN. “He walks in a room and the women start grabbing him and grabbing his ass and grabbing anything else they can grab on him.” Clinton: With the presidential race getting heated, allegations of extramarital affairs began to plague Clinton’s husband. Namely, Gennifer Flowers – a former Arkansas state employee – alleged that she and Bill had a 12-year affair, during much of his marriage to Hillary. To combat reports, the pair appeared together on 60 Minutes, but Hillary Clinton’s comment that she was not “some little woman standing by my man like Tammy Wynette” caused backlash. A few months later, when asked if her work at a Rose Law conflicted with Bill’s candidacy in relation to the Whitewater controversy, Clinton remarked, “I suppose I could have stayed home and baked cookies and had teas.” The comment was another chip at the campaign. Soon, she earned the blistering title of “Lady Macbeth of Little Rock,” a lasting comparison introduced by The American Spectator. None-the-less, Bill was elected that November, and sworn in the next year.


Trump: Trump and Marla Maples welcomed daughter Tiffany in October, who is now 23. Then, in December, the pair wed at the Plaza in front of 1,100 people. Clinton: President Clinton took office in January 1993. That month, Bill named then-First Lady Clinton to chair a task force on national health care reform, and she helped create the reform package that was unofficially referred to as “Hillarycare.” It was heavily opposed in Congress and the bill was declared dead the next year. Seven employees were let go from the White House travel office in May of 1993 – dismissals that later lead to the so-called “travelgate,” reported the Times. In June of that year, deputy White House counsel Vincent Foster filed three years of delinquent Whitewater corporate tax returns. The next night he was found dead of a suicide.


Trump: Trump increased his focus on his entertainment appearances in 1994, appearing in an episode of the Fresh Prince of Bel-Air, and then, controversially, a Playboy Centerfold video. In the video, Trump took photos of fully clothed models with a Polaroid camera, and then interviewed a potential Playmate for the 40th anniversary cover of Playboy magazine. Other scenes in the video without Trump featured fully naked women. Clinton: The Whitewater controversy – which stemmed from a 1978 joint-purchase of 220 aces of land in Arkansas by the Clintons and friends James B. and Susan McDougal, according to the Post – ramped up in 1994. Ties between the Clintons and the McDougals expanded when Hillary Clinton, then the First Lady of Arkansas, began doing legal work for James’ savings and loan, which had been engaging in questionable lending practices. In the summer of 1994, the Post reports, the House and Senate banking committees began Whitewater hearings. All 29 people that testified at the hearings were cleared of any wrongdoing.


Trump: The New York Times recently reported that Trump reported a $916 million loss on his 1995 tax returns, allegedly allowing him to avoid paying federal income taxes for up to 18 years. In 1995, Trump was also inducted into the Gaming Hall of Fame, which recognizes achievements in the gaming industry, according to the American Gaming Association’s website. The real estate mogul sold the Plaza Hotel that year, as well. Clinton: Clinton delivered a speech at the Fourth World Conference on Women in Beijing, China, in September 1995, addressing violations of women’s rights in the country. “It is a violation of human rights when women are doused with gasoline, set on fire and burned to death because their marriage dowries are deemed too small,” she charged in the emotional speech. However, the most famous line from her speech, one that has endure to this day, was, “If there is one message that echoes forth from this conference, let it be that human rights are women’s rights and women’s rights are human rights, once and for all.” She also began publishing the “Talking It Over” column for the Creators Syndicate, penning articles about policy and her experiences as First Lady.


Trump: Trump acquired 40 Wall Street in N.Y.C., turning the long-vacant office into the Trump Building. The building is now, according to Bloomberg, the most valuable property in Trump’s portfolio. In 1996, Trump began his foray into the pageant world, purchasing the Miss Universe organization, which includes the Miss Universe, Miss USA, and Miss Teen USA pageants. Last year, he sold the entire organization to WME/IMG. Trump’s pageant involvement has proved controversial, with some former contestants alleging that he acted inappropriately toward them during competitions. He has denied those claims. Clinton: It Takes a Village, Clinton’s book about her vision for America’s children, was published in January 1996 to mark the new year. Later that month, Clinton became the first, First Lady to be subpoenaed to testify before a federal grand jury in relation to Whitewater, reported the Times. Her husband was re-elected to a second term.


Trump: Trump’s next book, The Art of the Comeback, was released in 1997 – the same year as his separation from Maples. Their divorce was finalized two years later. In 1997, Trump made a joint-appearance with 1996 Miss Universe Alicia Machado, during which he controversially poked fun at weight she had recently gained. The video resurfaced this year when Machado began campaigning for Clinton. Clinton: In 1997, Clinton became the first American First Lady to win a Grammy Award, taking the statuette for best spoken word album for It Takes a Village. Working with Senators Ted Kennedy (a Democrat) and Orrin Hatch (a Republican), Clinton pushed for the passage of the Children’s Health Insurance Program, which helped children whose parents couldn’t provide them with coverage. In November 1997, she pushed the Adoption and Safe Families Act through to law, which made improvements to the national foster care system.


Trump: Melania Knauss, now known as Melania Trump, began dating the billionaire in 1998 after meeting him at a Fashion Week party, according to the New York Post. That year, when asked if he’d ever vie for the White House, Trump teased, “Can you imagine how controversial I’d be?” Clinton: In 1998, the Clinton family’s time in the White House completely revolved around the Monica Lewinsky scandal. News of the affair first broke that January, with then-White House intern Lewinsky alleging that she had multiple sexual encounters with the president from 1995-1997. The president denied the allegations, famously saying during a press conference, “I did not have sexual relations with that woman, Miss Lewinsky.” By August, however, DNA evidence forced Bill to admit in a taped grand jury testimony that he had an “improper relationship” with Lewinsky. In December of that year, Bill was impeached on perjury and obstruction of justice charges. He was acquitted of all charges. Throughout the ordeal, Clinton supported her husband.


Trump: Trump founded Trump Model Management, which was housed in New York City’s SoHo district. The modeling company has also been shrouded in controversy, with many former models alleging that they were financially exploited and were brought to the U.S. on travel visas, and then employed before obtaining work visas. A 2014 lawsuit against the company alleging similar practices was dismissed earlier this year, reported Forbes. Clinton: The Clintons purchased a home in Chappaqua, New York, after a Democratic seat opened in the U.S. Senate, according to the Times. She also helped enact the Foster Care Independence Act of 1999, expanding the funding and services provided to help those who are about to age out of the system.


Trump: In 2000, Trump created an exploratory committee into seeking the presidency on the Reform party’s ticket, as he detailed in an op-ed for the Times. He won the California and Michigan Reform primaries, according to The Hill, but ultimately left the race claiming that the party couldn’t adequately support a run for president. Clinton: Early in the year, Clinton formally announced her campaign for Senate. She was elected in November, marking the first time a sitting First Lady was elected to hold public office, said the Times that year. Clinton defeated Republican Rick A. Lazio, who only stepped in after former N.Y.C. mayor Rudy Giuliani withdrew for health and personal reasons. The final report on the Whitewater investigation was also issued in 2000, said the Associated Press. In total, the investigation lead to 12 convictions, but ultimately determined that there was insufficient evidence to prove that Clinton and her husband “knowingly participated in any criminal conduct.” Further, a coffee table book by Clinton called An Invitation to the White House was published.


Trump: The Trump World Tower was completed in Manhattan in 2001. The candidate also made a cameo in popular comedy Zoolander. Clinton: Sworn in on January 3, Clinton began her time as a New York senator. That year, she was appointed to the Committee on Budget, the Committee on Environment and Public Works, and the Committee on Health, Education, Labor and Pensions. After September 11, Clinton visited the site of the Twin Towers, securing a commitment of $20 billion to rebuild New York from President Bush, and voted for the Patriot Act, according to Clinton controversially voted ‘yes’ on overhauling the bankruptcy system, the Times reported, noting that she later expressed regret for supporting the legislation.

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Trump: Trump purchased the old New York City Hotel Delmonico for $115 million, refurbishing and reopening it a few years later as the Trump Park Avenue. He also reached a 5-year deal with NBC to air the Miss Universe pageants – moving away from CBS, where they had long aired, reported the Times. Clinton: Clinton voted in favor of the Iraq War in 2002, something she has recently referred to as a “mistake,” said the Chicago Tribune.


Trump: Donald Trump partnered with Mark Burnett to executive produce their long-running hit, The Apprentice. They begin promoting the show in 2003. Clinton: Clinton released her lengthy autobiography Living History. She was appointed to the Committee on Armed Services that year.


Trump: The first season of The Apprentice premiered in January 2004, and Bill Rancic was named the winner. Trump’s catchphrase from the show, “You’re fired,” became widely popular. There were 10 total seasons, and a spin-off, The Celebrity Apprentice, was launched in 2007. In 2004, he also got engaged to Melania, proposing in April. Clinton: In 2004, Clinton announced her plan to campaign for re-election in 2006, said the Times. She also spoke on the Senate floor, that year, against a proposed federal amendment that would have banned same-sex marriage, said Politico. During the speech, though, she said she believed that marriage should be a “sacred bond between a man and a woman.” Her position on same-sex marriage has since changed.


Trump: In 2005, Trump was caught on a hot microphone telling former Today show anchor Billy Bush that because he’s a “star” he can grab women “by the p—-.” The controversial tape was released just last month. That same year, the businessman launched Trump University. The school promised to teach students how to get rich in real estate, like Trump. Trump U is currently facing a class action lawsuit brought by some of the school’s former students, reported the New Yorker. In June, New York Attorney General Eric Schneiderman called Trump U “fraud from beginning to end.” Schneiderman said that “initial estimates are that personally pocketed 5 million” from the now-defunct program. Also in 2005, Trump wed Melania in Florida. Clinton: In conjunction with two other senators, Clinton introduced the Family Entertainment Protection Act, a bill designed to criminalize the sale of Mature-rated video games to minors, according to the Post. The bill was ultimately shut down.


Trump: Trump and Melania welcomed their son, Barron, in March 2006. Also in 2006, Trump commented that he “sort of hope” that the real estate market would crash, reported CNN. Two years later, it did. Clinton: In Nov. 2006, Clinton won her Senate re-election bid with 67 percent of the vote. She changed her stance on same sex marriage that year, again, saying that she would support states’ decisions in the matter.


Trump: In 2007, Trump received a star on the Hollywood Walk of Fame. The star has recently been the subject of vandalism. The same year, Trump was caught lying 30 times during a December deposition in his lawsuit against Trump Nation: The Art of Being Donald author Timothy L. O’Brien, reported the Post. In O’Brien’s book, he cited sources that called into question Trump’s net worth. In retaliation, Trump filed the suit against O’Brien, accusing him of dishonesty. The case was dismissed in 2009, as well as Trump’s appeal two years later. Clinton: Clinton announced that she was launching an exploratory committee into running for the presidency in 2008, saying in a statement, “I’m in to win.” She began campaigning that summer with the former President by her side, visiting key state Iowa ahead of the 2008 primaries, reported Reuters. At the time, she was leading national polls against competitors Barack Obama and John Edwards. That fall, Clinton unveiled her American Health Choices Plan, which centered around ensuring health coverage for all. Despite a major fumble during an early Philadelphia debate against her Democratic opponents, Clinton improved while facing off with Obama and Edwards in Las Vegas later in the year. From left; Donald Trump, Jr., Donald Trump, Melania Trump and Barron Trump (NPX/STAR MAX/IPx)

2008 Trump: In 2008, Trump put his weight behind then-Republican presidential candidate Sen. John McCain, said CNN. He also lauded McCain’s running mate, then-Alaska Gov. Sarah Palin, praising her to the network as making “a tremendous impact. The impact that she has had on rejuvenating almost the Republican Party, it’s been unbelievable.” Clinton: At the start of the year, Clinton fell to her opponents in the Democratic Iowa caucus, placing third behind Obama and Edwards. Despite a comeback in New Hampshire, she fell to Obama in the South Carolina primary. On Super Tuesday, Clinton won only California, New York, New Jersey and Massachusetts. A long string of losses to Obama followed, and despite a Pennsylvania win, by May it was clear that Clinton would not secure the nomination. She formally ended her campaign in June of that year, endorsing Obama. After conceding, Clinton took to the campaign trail for her former opponent and was ultimately promised the secretary of state position.


Trump: Trump magazine folded in 2009, after publishing in various iterations since the late 1990s, said the Daily News. In 2009, Trump Entertainment Resorts – his Atlantic City casinos – also went into bankruptcy. The group missed a $53.1 million bond interest payment in December of that year, thus resulting in Trump’s resignation as chairman. He further relinquished his corporate stake in Trump Entertainment Resorts to only 10 percent. Clinton: After Senate confirmation hearings, Clinton was approved as Secretary of State with a 16-1 vote. Clinton was the first former First :ady to be appointed to a U.S. cabinet. At the time, she made clear her goal to end the Iraq War. During her first year in office, Clinton visited Japan, Indonesia, South Korea and China, then in March, Israel. She later met with the presidents and leaders of countries including Egypt, Mexico, Turkey, Switzerland, Germany and Iraq. Clinton’s intervention led to Turkey and Armenia signing a historic accord in Oct. 2009, reported CBS. The accord re-established diplomatic relations between the countries and re-opened their shared border, which had been closed for 16 years. By the end of the year, Clinton held a 75 percent approval rating among 800 registered voters who said they regularly watched the news, reported Politico.


Trump: In 2010, Trump toyed with running for the presidency in 2012, telling ABC’s George Stephanopoulos that he was “thinking about things.” When asked what would change if he was president, Trump said, “Well, I’d do things very strongly. I’d tax China. They manipulate the currency. By manipulating the currency, it’s very hard to compete with China. As a big buyer of products, I will tell you I buy Chinese products because it’s very hard to compete with China.” Clinton: Clinton helped the U.S. impose sanctions on Iran, which eventually lead to the Iran nuclear deal, which was signed by the five permanent members of the United Nations’ security council and the European Union. She also made a visit to Haiti after the catastrophic earthquake, reported Reuters, and visited Chile after a devastating 8.8-magnitude quake killed over 700, said CNN. The Clintons’ daughter, Chelsea, wed Marc Mezvinsky in the summer of that year. In late November 2010, WikiLeaks began releasing 250,000 leaked classified cables from the state department, reported CNN. The cables dated back to 1966. Clinton lead much of the damage control, said the Post. She said of the leak, “Let’s be clear: This disclosure is not just an attack on America’s foreign policy interests. It is an attack on the international community – the alliances and partnerships, the conversations and negotiations that safeguard global security and advance economic prosperity.”


Trump: Trump dominated the news cycle with his support of the birther movement: a campaign that focused on proving that President Obama was not born in the United States, said the Post. In response, Hawaii released Obama’s long-form birth certificate in April. Shortly after, Trump attended the White House Correspondent’s dinner in Washington, D.C., with Melania. His birther theories became a main topic of the evening, and the businessman was the subject of ridicule at the hands of host Seth Meyers – and Obama himself. In May, Trump formally shut down rumors of a 2012 run for the White House, saying in a statement, “After considerable deliberation and reflection, I have decided not to pursue the office of the presidency.” In the statement, according to CNN, Trump said that he had the ability to “bring important economic and foreign policy issues to the forefront of the national dialogue.” Clinton: In May of 2011, al Qaeda leader Osama bin Laden was killed by U.S. Navy SEALs in Pakistan. Clinton was in the White House Situation Room watching the mission. Earlier in the year, Clinton pushed the U.N. Security Council to pass a resolution that authorized “all necessary measures” be taken against Libyan leader Moammar Gaddafi amid the Libyan civil war, according to the Post.


Trump: The businessman formally endorsed Republican candidate Mitt Romney for president after shutting down rumors of his own candidacy the year prior. Clinton: In early 2012, Clinton revealed that she had no intention on seeking another term as Obama’s Secretary of State. September of that year marked the controversy that has followed Clinton throughout her 2016 campaign: Benghazi. Four Americans – including U.S. Ambassador Chris Stevens – were killed after a U.S. outpost in Benghazi, Libya, was attacked. Immediately after the attack, the Obama administration publicly claimed that it was spontaneously spurred by an anti-Muslim YouTube video, reported the Post. Backlash arose over that claim, along with the administration’s reluctance to admit that the attack was, in fact, a terrorism exacerbated by lack of security at the consulate. Clinton later blamed the “fog of war” for initially claiming the attack was motivated by the video. In a report issued by the House Benghazi committee, Republicans blamed Clinton for misleading the public, “rather than tell the American people the truth and increase the risk of losing an election.” In the most recent report released by the committee in June 2016, Democrats concluded, “it remains unclear to this day precisely what motivated all of the individuals in Benghazi on the night of the attack.” The Benghazi situation would also play into Clinton’s email scandal, which the FBI investigated this year.


Trump: In 2013, Trump was inducted into the WWE Hall of Fame’s Celebrity Wing. He sued comedian Bill Maher for $5 million dollars after the TV host started a joke campaign to prove Trump’s father was not an orangutan, said Reuters. Maher sarcastically offered $5 million dollars to whomever could prove the claim, but after Trump submitted his own birth certificate and did not receive the funds, he retaliated. Trump eventually dropped the suit. Clinton: Clinton ended her tenure as Secretary of State on February 1, 2013. That year, she also finally paid off her campaign debt from her 2008 run, reported CNN. In June 2008 – just ahead of Clinton’s concession to Obama – her presidential committee owed $12 million to almost 500 creditors, said CNN. A hulking $13.2 million was owed to Clinton herself – money she had loaned her campaign. Also in 2013, Clinton earned numerous awards, ranging from but not limited to: the DOD Medal for Distinguished Public Service, the American Bar Association Medal and the Helen Keller Humanitarian Award. The Hillary Rodham Clinton Children’s Library and Learning Center also opened in Little Rock that July.


Trump: Expanding his hotel business abroad, Trump purchased the Turnberry golf resort in Scotland, reported the BBC at the time. The course had hosted the British Open four times before Trump purchased it. Clinton: Clinton released another book, Hard Choices, encompassing her time as Secretary of State, in 2014. Book sales were poor, reported the Post. Clinton’s daughter Chelsea, welcomed her first child, Charlotte, on Septemer 26. Clinton began regularly delivering paid speeches, earning more than a combined $25 million with former President Clinton in 2014, alone, said Politico.


Trump: On June 16, Trump announced his candidacy for the presidency in 2016. He promised, “I will be the greatest jobs president that God ever created,” and, “we are going to make our country great again.” Clinton: In April, Clinton announced that she would seek the democratic nomination for president in 2016. Clinton used a video to break the news, saying in the recorded clip, “Everyday Americans need a champion, and I want to be that champion. So you can do more than just get by, you can get ahead and stay ahead.”