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Trump Vs. Sanders : Political Careers Compared 1959 – 2016

Updated: Oct 12, 2019 10:10
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This is a timeline comparing the careers of Trump and Sanders, from high school all the way up to their presidential campaigns.  Trump and Sanders are arguably on polar opposites of the American political spectrum.  Both are also outliers in their current political parties, on the right Trump is a real estate mogul and reality TV star who is overtly disliked by Republican leadership.  Bernie in contrast is the first true leftist candidate to run for president since FDR, and since the Democratic brass and the corporate money have all lined up behind Hillary Clinton, Bernie has become the outlier of his party as well.

Democratic & Republican  presidential candidates Sen. Bernie Sanders, I-Vt. & Donald J. Trump. 2015 (AP Photo/Charlie Riedel)

While political pundits like Bill O’Reilly say that Trump and Sanders are ‘the same guy’…they’re both tapping into the anger of the voters.”  In reality their messages, careers & supporters couldn’t be any more different.  Bernie is talking about income inequality, free education, and universal healthcare, while Trump is talking about the dangers of immigration, the incompetence of government and of course his nebulous campaign slogan ‘make America great again.’  While Trump’s critics compare him to a fascist dictator, Sander’s critics say he’s an un-american socialist.  Let’s look at their careers side by side shall we?


Bernie Sanders is 74 years old and born in Brooklyn NYC,  Donald Trump will be 70 this June and was born in Queens NYC.  But that is where their similarities end.

Sanders high school photo attended 1955-59. Trump at a Military academy photo attended 1959-63

Bernie Sander’s father was a Polish immigrant who sold paint for a living and his mother was born to parents who had survived the Holocaust.  Bernie grew up poor and Jewish in a rent controlled apartment and went to public school.  Both of Bernie’s parents died shortly after he graduated high school.  He got himself through the University of Chicago, and then a graduate degree in Social Research. (cbs video interview with Bernie about his early life)

Donald Trump’s father was one of the wealthiest men in New York.  Trump went to private schools, got an MBA and after graduation he was given control of his father’s real estate empire, reportedly worth some 200 Million dollars at the time.

Get one of our new Bernie Sanders Shirts. $6 of each sale gets donated to Bernie’s campaign.


In the 1960s when the military draft for Vietnam was on, neither candidate went to war. Bernie was anti-war and had a college deferment while Trump despite going to military academy and playing on several sports teams, used his father’s connections to get a medical deferment for a ‘bone spur’ in his foot that no one actually believes existed.  It was around this time in 1967 that Senator John McCain was shot down, imprisoned and tortured while fighting in Vietnam.  Trump famously called McCain a ‘loser’ during a news conference in 2015, he explained “He’s not a war hero,” Trump said, “He was a war hero because he was captured? I like people who weren’t captured.”

Bernie’s Early Career

1963 – Bernie at Anti-Segregation Protest

Sanders being arrested at a 1963 anti-segregation protest in Chicago

1963 – Bernie Marched on Washington with MLK

It’s unconfirmed if it is Bernie in this photograph, what is confirmed is that he marched on Washington w/ MLK

1963 – Trump Marching at Military Academy

Donald’s Early Career
1971 – Father & Son

After his MBA at Wharton School of economics Donald was hired by his father Fred Trump, and in 1971-72 made President of his father’s real estate holdings worth approximately $200 Million.  (Fred & Donald shown here). By 1976, Trump is in full swing in his Manhattan Penthouse.  He has already inherited $40 Million from his father, and before long he will use his family’s fortune to put his name on large buildings.  Although is father made his fortune building apartments for working class people, Trump Jr. will aim at the upper class.

The Gov Sues Trump Biz for Discrimination

Via –

In the early 1970s Donald Trump was made president of his father’s NY real estate empire worth approx $200 Million dollars.  One of Donald’s first challenges came in October 1973, when the Justice Department hit the Trump Organization with a major discrimination suit for violating the Fair Housing Act. The Times reported:

… the Government contended that Trump Management had refused to rent or negotiate rentals “because of race and color.” It also charged that the company had required different rental terms and conditions because of race and that it had misrepresented to blacks that apartments were not available.

The journalist Gwenda Blair reported in her 2005 Trump biography that while Fred Trump had sought to combat previous discrimination allegations through “quiet diplomacy,” Donald decided to go on the offensive. He hired his friend Roy Cohn, the celebrity lawyer and former Joseph McCarthy aide, to countersue the government for making baseless charges against the company. They sought a staggering $100 million in damages.

A few months after the government filed the suit, Trump gave a combative press conference at the New York Hilton in which he went after the Justice Department for being too friendly to welfare recipients. He “accused the Justice Department of singling out his corporation because it was a large one and because the Government was trying to force it to rent to welfare recipients,” the Times reported. Trump added that if welfare recipients were allowed into his apartments in certain middle-class outer-borough neighborhoods, there would be a “massive fleeing from the city of not only our tenants, but communities as a whole.”

In contrast, while Trump and his father were sued by the government for withholding housing from African Americans, Bernie Sanders led a sit-in to protest segregated housing for black students while he was a student in Chicago in the 1960s.

Bernie Sanders (standing), then a college student at the University of Chicago, leads his classmates in a sit-in to protest segregated housing for black students. (Danny Lyon/Special Collections Research Center, University of Chicago Library)

Bernie in Politics
1970s – Fight for social equality

While Donald at 25  years old was given a multi million dollar empire, Bernie was speaking out against the Vietnam War, running for political office in Vermont, and writing letters to his constituency standing up for Pro-choice ideals, peace, and social equality.  By all accounts he was ahead of both major parties when it came to social justice and equality.  But his little known Liberty Union party (socialist democrats) did not have the funding or recognition to compete in large elections.

Mayor Sanders of Burlington Vermont

In the 80s Bernie was ahead of nearly everyone on many social issues, but gay rights really stand out.  As Mayor of Burlington Vermont in the early 80s he signed a Gay Pride Day proclamation, and in the House of Representatives (1996) he was one of just 67 members to vote against the anti gay Defense of Marriage Act (DOMA).

Mayor Bernie 1981

Trump Business In the 1980s

In the early 80s Trump was busy putting the family name on the side of large buildings, and his net worth grew into the billions.

But the late 80s and early 90s were a tough time for Trump.  He was using his family’s fortune to buy up risky and insolvent casinos, and his estimated net worth dropped from $3 billion, back down to $400 million.  It is widely speculated that he would have done much better financially by putting his inheritance into an index fund, instead of managing it himself.  To make matters worse his first marriage was on the rocks.  In a divorce deposition Trump’s ex-wife Ivana used the word “rape” to describe an incident between her and Donald in 1989. More recently since Donald began running for president Ivana has distanced herself from those comments, saying now that they have no merit.  Her statements about their marriage decades ago, were taken under oath.

Trump’s lawyer at the time, Michael Cohen was infamous for bullying people and he threatened the reporter at the Daily Beast not to write about the rape allegation.  Cohen told the writer, quote: “I will make sure that you and I meet one day while we’re in the courthouse. And I will take you for every penny you still don’t have. And I will come after your Daily Beast and everybody else that you possibly know,” Cohen said. “So I’m warning you, tread very fucking lightly, because what I’m going to do to you is going to be fucking disgusting. You understand me?”  Via –

Trump has since distanced himself from his Cohen.

Trump’s 1st Bankruptcy

In 1991 Trump’s Taj Mahal casino in Atlantic City filed for bankruptcy, the first and most significant of the four bankruptcies that he experienced.  In his defense he said, “I didn’t want to have any personal liability, so I used junk bonds. I accept the blame for that, but I would do it again,” he said.  “This was not personal. This was a corporate deal,” he said to reporters, “If you write this one, I’m suing you.” (read about all four bankruptcies here)


Bernie House of Representatives
1991 – 2007

The other 99.7% wouldn’t be affected by Sen. Sanders proposal to toughen the estate tax. (Credit: Getty Images)

From 1991 to 2007 Bernie was serving in the US House of Representatives working on reducing poverty, helping the environment and punishing white collar crime.  In 1995 the Sanders Amendment of Corporate Crime Accountability.  Required, “offenders who are convicted of fraud and other white-collar crimes to give notice to victims and other persons in cases where there are multiple victims eligible to receive restitution.”

Bernie was working to protect pensionsexpand free health care, increase funding for heating for the poor, fighting corporate welfare and on and on.  Despite the fact that the most right-wing Republicans in a generation controlled the House of Representatives between 1994 and 2006, the member who passed the most amendments during that time was Bernie Sanders.  A great list of his amendments and reforms can be found here.

In Contrast, while Trump was making risky white collar bets, losing them, and then passing the debts to others using Chapter 11 laws, Bernie was busy passing federal legislation that penalized such behavior.

Trump in Politics & Pageants

Trump’s parting shot, “You’re fired,” a national catchphrase.

Trump entered the Presidential race as an Independent in 2000, but he dropped out of the race months later.  Then in 2001 he switched to the Democratic party, only to register as a Republican in 2009.   In 2005 he had his 3rd marriage to a different model, and began acting on and producing The Apprentice TV series.

The apprentice ran from 2004 – 2015 and was largely a television success.  The show helped Trump rebound back into the public spotlight after 2 of what would end up being 4 bankruptcies in total.   While Sanders was serving in the House and US Senate, Trump spent roughly the same amount of years producing Beauty Pageants, the Miss Universe Pageant to be exact.

Bernie’s Recent Public Record:

Bernie most recent Bill’s in the Senate:

View All here

Trump’s Recent Public Record:

IMBD Producer Credits:

2014 Miss Universe 2014 (TV Special) (executive producer – as Donald J. Trump)
2013Miss Universe 2013 (TV Special) (executive producer – as Donald J. Trump)
2012Miss Universe 2012 (TV Special) (executive producer – as Donald J. Trump)
2012The 2012 Miss USA Pageant (TV Special) (executive producer)
2008-2012The Apprentice (TV Series) (executive producer – 8 episodes)
2010The 2010 Miss Universe Pageant (TV Special) (executive producer – as Donald J. Trump)
2010Donald J. Trump Presents: The Ultimate Merger (TV Series documentary) (executive producer)
2009Miss Universe Pageant (TV Special) (executive producer)
2009Miss USA 2009 (TV Special) (executive producer)
2009The Girls of Hedsor Hall (TV Series) (executive producer – 2 episodes)
2008The 57th Annual Miss USA Pageant (TV Special) (executive producer)
2007Pageant Place (TV Series) (executive producer – 1 episode)
2006Miss USA 2006 (TV Special) (producer – as Donald J. Trump)
2005The Apprentice: Martha Stewart (TV Series) (executive producer)
2005Miss Universe 2005 (TV Special) (executive producer)
2003Miss Universe Pageant (TV Special) (executive producer)
2002Miss Universe Pageant (TV Special) (executive producer)
2002Miss USA 2002 (TV Special) (executive producer)

Trump’s ‘Birther’ Political Movement

Trump was a famous ‘birther‘ from 2008-2011, meaning his Tea party fueled candidacy was based on accusing President Obama of not being born in the USA.  Obama released his birth certificate in 2011, and Trump was ridiculed in the press for a solid year.

Our comparison thus far may look biased, perhaps it is.  But we genuinely could not find many positive things to present about Donald J. Trump.  He has no real political record, what he does have is long career of gambling with investments using other peoples’ money, making sexists and racist comments, and changing his political leanings when it is convenient.  The only clear success Trump has had is as a reality tv star and as a producer for beauty pageants.  In a sense, he plays a successful guy on television and that’s about it.  It has been argued and confirmed by many financial experts that Trump would have done much better with his inheritance if he had put it in an index fund in the 80s, instead of trying to manage it himself.  His success, like his political acumen, is nothing more than a show.  Trump is rich, because he was born rich, not because he is a great business man or investor.

Bernie has had a long political career.  He was fighting for racial equality in the 60s and for gay marriage in the 80s, long before it was politically ‘OK’ to do so.  He was one of the few who stood up against the war in Iraq and against the de-regulation of Wall Street that lead to the 2008 collapse.  How many things does he have to be dead right about in order to get broad public support?

He doesn’t take money from corporate super PACs and he’s the only candidate talking about the reality of climate change.  There is a reason that millennials overwhelmingly support him, he actually cares about their futures. They can see that he was right about all of the important social issues years before the other politicians came around.  He’s a politician that actively fights for socialized medicine and making education a real priority in this country.  Corporate interests want you to see this as ‘socialism’, but what it is, is our inevitable future.  We all know we are going to get a more a European system in regards to socialized medicine, education and alternative energies use eventually, it is the only path that makes social and financial sense.  Conservatives are afraid of change, and the corporations simply want to slow things down to protect their profits in the short term. Bernie knows where we’re going, and he’s tired of us being behind the curve.

Corporate interests want to delay these social eventualities because of greed, Bernie simply wants America to stop waiting around.

In closing:

Wanna support Bernie and look fly while doing so? Get one of our new Bernie Sanders Shirts. $6 of each sale gets donated to Bernie’s campaign.

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Alex Mak - Managing Editor

Alex Mak - Managing Editor

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