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How Donald Trump Won the Presidency in 2016

By Gary Mills in Politics
| October 30, 2020 12:22 pm PDT
How Donald Trump Became President

There are some who say this man had no business running for the most powerful office in the world.

He had no political experience. More than two dozen women accused him of sexual assault. He failed in multiple businesses and has borrowed tens of millions without ever paying it back.

Yet despite all these shortcomings, this guy beat political veteran Hillary Clinton in 2016 to become the 45th president of the United States.

That man is Donald J. Trump.

“I think in a lot of people’s minds, what Trump has proved is that anybody can run for president. And in a lot of people’s minds, what he’s also proved is that not everybody should run for president.”Dwayne “The Rock” Johnson

I was as surprised as anyone when he won. I thought that Hillary Clinton was going to beat him, no problem at all.

She did beat him in the popular vote. Clinton garnered nearly 3 million more votes than Trump. However, he beat her where it counts — the Electoral College, where he received 290 votes to her 227.

Trump is the fifth president in history to win an election without winning the popular vote.

And I want to explore how that happened. How a man with so much negative baggage and zero experience managed to garner enough votes to become the most powerful man in the world.

The following is my analysis of how Donald Trump became president of the United States.

Trump Promised to Make America Great Again

I think a contributing factor to Trump winning the presidency was the promises he made.

Not just any promises. All candidates make lots of them. It was the type of promises he made that earned him so much support.

His promises appealed to the working class. The patriots. The people tired of seeing Americans hurt by crimes committed by and our resources going to undocumented immigrants.

The following list is some of his biggest campaign promises that I think appealed the most to American citizens.

To Be the “Greatest Jobs President”

One promise Trump repeated over and over again was that he was going to create more jobs. He played up his business success on the campaign trail and claimed to have created 10,000+ jobs.

He stated that he was going to be the “greatest jobs president.”

In fact, with only two months left to go before the election, Trump rolled out his economic plan. This plan showed Trump’s idea for how to add 25 million new jobs and boost the economy by 3.5%.

His plan would not cut into Social Security, Medicare, or Medicaid. It would not impact defense spending, either.

Trump (and his economic team) estimated that nearly $2 trillion would be eliminated from the nation’s debt with this plan. Only $800 billion would remain, which Trump figured could be eliminated after a decade.

Spoiler alert — that hasn’t happened yet.

No wonder there were many people skeptical about his proposed 4% growth rate.

One of those skeptics was Barack Obama.

To Bring Manufacturing Back to the US and Impose Tariffs on Imports

This promise went hand-in-hand with creating more jobs.

Trump promised to bring manufacturing back to the United States. This would create more jobs (instead of shipping them overseas) and — in theory — boost the economy.

“Skilled craftsmen and tradespeople and factory workers have seen the jobs they loved shipped thousands of miles away.”President Donald Trump

He also promised to impose new tariffs on goods imported from China and Mexico. This would increase the costs of goods produced by these countries, which might encourage consumers to buy domestically.

This was a huge promise. So big, in fact, that many people left the Democratic Party after hearing it.

To Build a Wall and Deport Illegal Immigrants

It doesn’t matter if you paid attention to this campaign or not — chances are, you heard about Trump’s promise to build a wall.

This wouldn’t be just any wall, either. It’d be a wall that would sit along the southern border between the United States and Mexico.

This border is approximately 1,900 miles long.

Many Americans viewed this promise as racist. However, many others viewed it as a way to secure our borders and to keep Americans safe from physical harm and contraband such as weapons and drugs.

One of the challenges to building this wall is that it’d be expensive. Trump estimated that it’d cost $5-$8 billion, while I’ve seen other estimates as high as $75 billion to build it.

The solution? Trump would make Mexico pay for it.

Another promise Trump made was that he planned to deport all the illegal immigrants in the United States.

He wanted to send them back home and have them come back legally, using the proper channels — even if it took longer to accomplish.

There was a lot of skepticism around this promise, too. It’s an incredibly expensive task to carry out. It costs roughly $10,000 to deport an individual. With more than 11 million illegal immigrants in the US, that’d run about $110,000,000,000 to pull off.

Of course, I’m sure no one thought about that while listening to Trump make the promise. All they heard was that this would protect citizens, protect our resources, and protect our jobs.

To Abolish Obamacare

Republicans hate Obamacare.

This might be why Trump promised to abolish it and replace Obamacare with something else.

Obamacare is a bill that requires everyone to get insurance or otherwise pay a tax. The idea is to subsidize health care for lower- and middle-income families so everyone can be covered. It also ensured that everyone could receive coverage, even if they had a preexisting condition.

Many Democrats didn’t like Obamacare because they didn’t think it went far enough towards a fully government-run healthcare system.

Republicans feel the opposite. They think it’s too expensive and doesn’t encourage a free market. And personally, I don’t like being told I have to have insurance.

Many people agree, which is why they voted for Trump.

To Cut Taxes

The final promises I want to highlight revolve around cutting taxes.

Trump promised to reduce both corporate taxes and taxes for working Americans.

The appeal is obvious here — who doesn’t want to pay fewer taxes?

Trump partially fulfilled this promise, too. He reduced corporate taxes from 35% to 21%. And he has managed to reduce taxes for most Americans, though middle- and upper-class families will benefit the most.

All these promises certainly helped Trump win the election. However, I think there’s more to him winning the election than making a few promises.

4 Additional Things That Helped Trump Win the Election

There are a few advantages and opportunities that Trump had during his campaign run that his opponents didn’t.

What’s more is that he knew how to leverage them.

I won’t go as far as to say that these advantages and opportunities secured his victory, but you can’t deny that they helped.

Here are the four advantages and opportunities that I think had the most impact on Trump winning the 2016 election.

Free Media

During his campaign run, Trump made the promise that he’d finance his own campaign. That way, he could portray himself as being free from lobbyists.  

“I don’t need anybody’s money. It’s nice. I’m using my own money. I’m not using the lobbyists. I’m not using donors. I don’t care. I’m really rich.”President Donald Trump

Trump kept his promise, but the truth is, he spent far less on his campaign than he should have for all the media coverage that he got.

The thing is, so many people thought that Trump was joking about running for president. Or that he was using his candidacy for publicity.

Many people thought he was entertaining.

So these various media platforms, such as radio shows, podcasts, and news shows on major networks, all gave him a ton of free airtime.

Experts estimate that Trump received $3 billon in free media by the end of the primaries and $5 billion by the end of the election. This is publicity that most people would have to pay for.

To put this into perspective, $2.4 billion was spent on the election between Barack Obama and John McCain, $1 billion of which was spent between the two of them.

Trump received 5x as much as Obama and McCain put together — and all of that was spent on publicity. This freed his budget up for other expenses such as advertising, staff, research, and strategy.

This gave Trump a massive advantage.

Trump’s Not a Politician

I think another advantage that Trump had was that he wasn’t a politician. He had no experience working as a governor or senator.

I’m sure some people thought this was a disadvantage. Many people probably want their president to have some experience before assuming the toughest and most important job in the United States.

However, there are tons of people who’re jaded with politics. They’re tired of the scandals, lies, and empty promises. And they know that many politicians are bought and paid for.

Many people view politics as pointless.

My theory is that these same people would rather vote for an everyday guy like Trump who isn’t influenced by other political bigwigs or lobbyists. They’d rather vote for Trump who’d work for them instead of a politician who’d only look out for himself.

Then there are some people who just want to shake things up. They voted for a regular guy like Trump just to see what happens.

And I think that was a huge advantage for him.

He Projected Success

While I didn’t vote for Trump, I’ll admit that I was on the bandwagon when I first heard he was running.

All I (thought I) knew about him was that he was a businessman who earned billions of dollars. I thought it was neat that someone like him would run and that his business experience would be good for America.

I point this out because I’m sure I wasn’t the only one. I bet lots of people thought or continue to think the same way.

These people see Trump on The Apprentice or know him as the guy who owns tons of buildings in New York and casinos in New Jersey. And that he had a piece in the Miss USA beauty pageants.

They thought this success would carry over to the presidency.

Trump Is Polarizing

Another advantage that Trump has is that he’s polarizing. He doesn’t hold back from pandering to a specific group of people while alienating the rest.

All politicians do this — naturally, considering that they join one party over the others. However, politicians are often willing to pander to specific people to get the votes they need.

I’m sure Trump does this too. However, what Trump does that few, if any, politicians do is attack a person or group of people that he has a problem with. He’ll do this on TV, podcasts, and on Twitter.

This often works to his benefit because the people he attacks are usually people his userbase doesn’t like either (or are easily persuaded not to like).

For example, his userbase is patriotic. Many are against immigrants coming into the country illegally, applying for welfare, and taking jobs from Americans.

So when Trump calls out Mexico for allowing people to migrate here, or Democrats for not wanting to build a wall to secure our borders, his supporters rally behind him.

The bottom line is that Trump has not shied away from making it clear who he wants to appeal to and who he wants to repel. This is a much better approach than trying to appeal to everyone because when you do that, no one will remember who you are.

And I think we can all agree that no one has trouble remembering who Donald Trump is.

This definitely worked in Trump’s favor during his 2016 campaign.

Did Russia Help Trump Win the 2016 Election?

Another advantage many people think Trump had is Russia. There’s a lot to this, so I’ll unpack the simple version.

The first hint anyone had that Russia was messing with the election was in September 2015. The FBI told the Democratic National Committee that at least one computer was compromised by Russian hackers.

Over the next 6-8 months, hackers made multiple phishing attempts. They managed to access 33 DNC computers. And they launched a website called DC Leaks to publish the data and documents they stole.

Someone also leaked this information to WikiLeaks. Their founder, Julian Assange, said in June 2016 that they received a batch of campaign emails they planned to publish.

WikiLeaks published 20,000 emails from the DNC server a month later. These emails included scandalous details about the DNC, such as how the DNC was favoring Clinton over Bernie Sanders.

That same month, the FBI launched an investigation. Shortly after, they announced that they believed the cyberattacks were linked to Russia.

The CIA Investigates and Concludes That…

The Washington Post reported that the CIA determined that the hackers were trying to help Trump win the election, while the FBI said they couldn’t find proof that that was the case.

Trump said the following year that while it was possible that Russia tried to influence the election, they couldn’t impact the election itself since they couldn’t hack the voting machines or computers that tallied the results.

He must’ve forgotten about all the negative ads and (fake) news posts they published about Clinton. Or the emails they leaked to the public that gave her tons of negative attention.

Fast forward to May 2017. Former FBI director Robert Mueller was appointed as special counsel to lead the investigation regarding Russia’s interference.

The following February, Mueller indicted 13 Russian nationals for (allegedly) interfering with the 2016 election. He charged them with conspiracy to defraud the United States.

The Senate Intelligence Committee released a report the following July. They said that their original assessment was correct — that the goal of the interference was to help Trump win the election.

In March 2019, Mueller ended his investigation. He stated that there wouldn’t be any more indictments.

Trump Denies Any Involvement

There’s a lot more to this. The investigations ran for several years. Then there were several connections made between Trump’s associates and Russian officials.

Then there’s the fact that Trump, his son, and many others associated with Trump had meetings with Russian contacts and ambassadors.

In fact, George Papadopoulos, a foreign policy advisor for the campaign, pleaded guilty in the Mueller investigation for lying to FBI agents about his Russian contacts.

What I find interesting is that the hackers didn’t just target the DNC or Hillary Clinton — they also targeted Republicans such as Lindsey Graham and Marco Rubio. Both Republicans were planning on running against Trump.

A little suspicious, no?

Anyway, according to Time.com, Trump (or his campaign) wasn’t found guilty of working with the Russian government. That said, Mueller’s investigation showed that there were people in Trump’s camp who were plenty happy to receive help from the Russians.

“If there’s any evidence that any of his interactions or campaign officials’ interactions with Russian officials might have influenced public policy decisions as President, I think that’s going to open the doors to more investigations. Even if they don’t have a criminal case that he directly conspired with the Russian government, there’s a lot in between that and nothing.”Julian Zelizer

How Hillary Clinton Helped Trump Beat Her in the 2016 Election

I’m sure Trump wouldn’t be bashful about his business acumen all the other reasons that helped him win the presidency.

And I have no doubt he could tell you where Clinton failed during her own campaign run.

Because I believe she did screw up. Multiple times.

Her screw-ups weren’t solely responsible for her losing the White House to Donald Trump. Elections are far more complicated than that.

However, the mistakes she made did help Trump beat her. I don’t think there’s any denying that.

What I want to do now is look at a few of the biggest mistakes Hillary made during her 2016 campaign run and how I think it hurt her.

Her Infamous “Basket of Deplorables” Quote

Hillary Clinton stuffed her foot in her mouth during a speech in September 2016 when she insulted half of Trump’s supporters.

Here’s what she said.

“You know, to just be grossly generalistic, you could put half of Trump’s supporters into what I call the basket of deplorables. Right? They’re racist, sexist, homophobic, xenophobic — Islamophobic — you name it. And unfortunately, there are people like that. And he has lifted them up. He has given voice to their websites that used to only have 11,000 people — now have 11 million. He tweets and retweets their offensive hateful mean-spirited rhetoric. Now, some of those folks — they are irredeemable, but thankfully, they are not America.”Hillary Clinton

She apologized for saying half, though she insisted that Trump has enabled hateful people to spread their views.

Diane Hessan, who tracked undecided voters for Clinton, said that Clinton’s comments caused the largest shift of undecided voters shifting towards voting for Donald Trump that she’s ever seen.

And political scientist Charles Murray said that her comment may have helped get Trump elected (and agreed with someone else who said that Clinton’s comment changed the history of the world).

Hillary Clinton agrees. She wrote in her 2017 book, What Happened, that her “basket of deplorables” comment was a factor in her (electoral vote) loss.

It’s such a big deal that her comment has its own Wikipedia entry.

(Allegedly) Lazy Campaigning in Key States

Many critics agree that another thing that Clinton failed to do is spend enough time campaigning in Michigan, Wisconsin, and Pennsylvania.

Each of these states usually votes Democrat, but in 2016, the states voted for Trump.

Clinton addressed this theory in her book, What Happened. She disagreed with the critics. Clinton said that the margins were razor thin — too thin to say for sure. The difference between her and Trump winning was only 40,000 people across all three states.

She also went on to point out that she was leading Trump in these states until October 28th. That was when Jim Comey (former director of the FBI) started to talk about Clinton’s email server.

Clinton believes Comey’s actions had far more impact on her campaign run than the time she didn’t spend in Michigan, Wisconsin, or Pennsylvania.

I agree with her that it’s hard to say for sure. That said, Trump spent exponentially more time in these states than she did.

Take that for what it’s worth.

Those Pesky Emails

Hillary’s emails were a big talking point during the 2016 election. Here’s a brief summary of what that was all about.

For the entire four years that Clinton was secretary of state (starting in 2009), she used a private email server from her home.

She didn’t use the servers owned and managed by the US government. This would’ve been smarter considering the type of information her emails probably contained.

Clinton said that she didn’t use the government’s servers because she didn’t want to manage multiple email addresses. She used her server for convenience.

Near the end of her tenure, it came to light that she was using her own server. The State Department requested that she send all work-related emails to them for review.

Clinton’s lawyer turned over 55,000 pages of emails. Several months later, she turned her server in.

While 32,000 emails were more or less personal, there were nearly 100 “secret” and “top secret” emails. And the State Department retroactively labeled nearly 2,100 more as classified.

She never faced criminal charges since she didn’t knowingly send or receive classified information. And the FBI has investigated this situation (at least twice) and determined that she didn’t do anything wrong.

This mistake bit her in the butt because she asked America to trust that she was complying with both the “letter and the spirit of the rules” during her campaign. Yet her “convenience” explanation is a poor excuse for risking potentially classified information.

Her emails negatively impacted her for the final time when James Comey mentioned that they were looking into the case again — 12 days before the election.

…only to announce a couple weeks later that he had not changed his mind — that Clinton should not face criminal charges for her actions.

The timing was awful, not to mention a little suspicious.

Ultimately, though, this was Clinton’s fault. Had she used the government’s servers, she would’ve avoided this whole fiasco.

And she might have become the first woman president of the United States.

Voters Wanted to Feel the Bern Instead

The last mistake Hillary Clinton made isn’t really a mistake at all. It still bit her in the butt, though. And that mistake was beating Bernie Sanders to become the presidential nominee.

You’d think that, by beating Bernie Sanders, many of his supporters would support Clinton instead come election day.

But you’d be wrong.

Instead of voting for Hillary Clinton, here’s what many of Bernie’s supporters did instead.

  • Not vote at all
  • Vote for Trump
  • Vote for a third party

All these alternatives hurt Clinton, especially in states like Michigan and Pennsylvania where she needed every vote.

For example, Green Party nominee Jill Stein won enough votes in each of these states that, had they gone to Clinton instead, it would’ve changed the election. Clinton would’ve won the presidency.

Of course, that’s only if they would’ve voted for Clinton. Had enough of them voted for Trump, he still would have won the election.

It’s still worth considering, though. And I find it interesting that people chose to vote for a third party instead, knowing full well that the third party wouldn’t win. They risked Trump winning the presidency instead of giving it to Clinton.

That says a lot, in my opinion.

Those are the biggest mistakes I think Clinton made that helped Trump win the presidency in 2016.

Remember, she lost despite winning the popular vote by nearly 3 million votes. She lost the presidency in the Electoral College. This was likely due to a variety of factors, including insulting potential voters, not campaigning in key states, and not being the Democratic candidate people wanted to vote for.

Of course, you could easily make the argument that none of these things mattered. That after eight years of Obama and Democratic leadership and policies, Americans were just ready for a different kind of leader.

Who would’ve thought that leader we were ready for was Donald Trump?


Donald Trump was the unlikely candidate to win the presidency. He shocked a lot of people who never thought in a million years that The Apprentice guy would be running the United States.

But he did, and there are loads of reasons why.

Trump’s polarizing. He’s not a politician. And he made big promises that appealed to the patriotic working class.

It didn’t hurt that he was running against Hillary Clinton, either, someone who made plenty of mistakes of her own and that an overwhelming majority didn’t like any more than him.

But thanks to the perfect storm, here we are. Those are what I see as the biggest reasons why Donald Trump won the presidency in 2016.

There are many lessons to take from this if you choose to bet on presidential elections. Not least the fact that you should expect the unexpected.

With the 2020 presidential election just around the corner, our team is covering things extensively on our politics blog. Be sure to take a look through our latest posts as we have tons of interesting content for you.

Here are some highlights.



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