Donald Trump Had a Chance to Win the First Debate. Here's How He Blew It.

September 27th 2016

Mike Vainisi

Trump. Clinton. The battle of the flawed titans. We've been waiting for this for months. Let's get right to it.

1. Trump's won the first 20 minutes of the debate, especially the section on trade policy.

Trump on trade debate.

For the first twenty minutes or so, Trump came off like the can-do, outsider businessman who just wants to bring some fresh solutions to America's longstanding problems. He started by staking an effective position on trade, pinning Clinton to the unpopular free trade agreements NAFTA and TPP. His strongest point of attack was questioning Clinton's sincerity in her opposition to TPP, which she had previously called the "gold standard" in trade deals.

Trump on Trade

With these attacks, Trump was speaking directly to the Midwestern Rust Belt, specifically Ohio, Michigan, and Pennsylvania — three states that have been hit hard by job losses associated with international trade deals and also happen to be critical to Trump's path to winning the election. Clinton did not have a good answer here, awkwardly defending free trade with platitudes about the number of countries in the world. And her attempt to re-frame the discussion around trickle down economics was weak, particularly the painfully corny line that Trump's economic plan is "Trumped up Trickle down."

Trump came off calm, reasonable, and almost jovial in the opening moments of the debate. It was a different kind of Trump than the gloom and doom version we saw at the Republican National Convention.

At this early point, you had every reason to believe that Trump was about to exceed expectations and win this debate.

But then the wheels fell off for Donald Trump.

2. Trump's explanation for not releasing his tax returns was a disaster.

Hillary on Trump Taxes

Things started to go awry for Trump when he was asked about his tax returns.

Here's the thing: Trump's refusal to release his taxes hasn't made sense for a year. And it still makes no sense. His canned line is that he's under an audit, so he's not allowed to release them. But then he's also said, as he did tonight, that they won't tell us anything anyway. But if they won't tell us anything, why not release them?

The problem here for Trump is that by not releasing the returns, he's left a total vacuum for Clinton to fill with suggestive questioning about his motives for not releasing them: What's he trying to hide exactly?

Clinton used the debate to openly question whether Trump was trying to hide the fact that he's not as rich as he claims. She also wondered if he owes money to dangerous people that could potentially cause conflicts of interest for him in the White House. And, most effectively, she questioned whether Trump even pays federal income taxes, citing two years of released taxes from the 1970s, which showed Trump paying a grand total of zero dollars to the federal government.

Trump on his taxes

Trump's response? Well, it was hard to tell, but it sounded like he basically confessed that he doesn't pay taxes, not once but twice. First, he said that his not paying taxes "shows that he's smart." A few minutes later, he said that even if he did pay taxes, the money "would be squandered anyway."

It's hard to believe a presidential candidate would make that kind of confession during a debate, but it's even crazier that he seemed to brag about it?

Even worse, when given the opportunity to use this issue to talk about Clinton's character, he totally failed to pivot the conversation to Clinton's email scandal.

This section was a total disaster for Trump.

3. Instead of denying that he's a racist, Trump answered with word soup.

Trump on Birtherism

Trump's second disaster came when he was asked to account for his association with the birther movement and his year-long campaign alleging that President Barack Obama wasn't born in the United States.

Look, his foray into birtherism was never going to be a good moment for Trump. If anything, he was probably hoping to get this out of the way in the first debate.

But instead of quickly dispensing with the issue — hell, even admitting he was wrong and showing some humility — Trump tried to turn the tables and accuse Clinton's 2008 campaign of starting birtherism. So, Trump's response to despicably backing birtherism was to accuse Clinton of also espousing birtherism and acting "holier than thou," as he put it.

The thing is, even if Trump was right and Clinton operatives started those rumors in 2007 or 2008 (and there's no evidence they did), it was Trump who embarked on a nationwide birtherism crusade four years later.

Clinton used the opportunity to get in some devastating body blows.

"He started his political activity based on this racist lie that our first black president was not an American citizen," Clinton said.

How did Trump respond? Did he adamantly deny that he has a racist bone in his body?

"I did a great job and a great service, not only for the country, but even for the president, in getting him to produce his birth certificate."

Yikes. The birther issue is a classic example of something that plays well or even neutral among a Republican primary electorate, but looks awful when you ask all Americans. While more than 72 percent of Republicans still doubt whether Obama was not born in the U.S., a recent YouGov poll found that not only do 61 percent of Americans think the president was born in the U.S., but also that more than half believe Trump should apologize for his birther attacks.

Similarly, when Clinton brought up the Justice Department's two lawsuits against Trump for racially discriminating against prospective black renters, he didn't unequivocally deny the charges of racism. He instead blamed it on his father...or something?

“When I was really young, I went into my father's company, we along with many, many, many other companies, throughout the country, it was a federal lawsuit, were sued. We settled the suit with zero — no admission of guilt. It was very easy to do. But they sued many people.” (h/t to Politico for the direct quote.)

4. Trump somehow turned the Iraq War into a strength for Hillary Clinton.

Now we come to the Iraq War.

Traditionally, Clinton and Iraq have sort of been like Shaquille O'Neal and free throws. It's her Achilles' heel.

Just ask President Obama, who used her 2002 vote to authorize the invasion of Iraq to not only deny her the Democratic presidential nomination in 2008, but probably the White House.

Somehow, Trump turned this negative into a positive for Clinton.

Let's back up for a second. Throughout the long slog of the Republican primary season, Trump used Iraq as an attack line against his Republican opponents. He cited Republican President George W. Bush's decision to invade Iraq as one of the biggest reasons that the GOP needed new leadership.

It was a powerful and effective argument, especially given the fact that 51 percent of Americans believe the invasion of Iraq was a mistake, according to a 2015 Gallup Poll. Trump always went a step further, though — claiming not only that Iraq was a terrible decision (which it was), but also that he had the brilliant foresight back in 2002 to know that it was a horrible idea.

The problem is that Trump has never been able to prove he was against the war. In fact, when Howard Stern asked him about Iraq in 2002, Trump offered lukewarm support.

Specifically, Trump told Stern, "Yeah, I guess so; I wish the first time it was done correctly," when asked if he supported an attack on Iraq.

Trump's overstepping on this issue was once again exposed during the debate. Instead of attacking Clinton for her decision — as an elected member of the U.S. Senate who cast a vote for the war — he bickered with moderator Lester Holt over whether he supported the war at the outset. It's an easily verifiable fact that Trump did not oppose Iraq from the beginning, yet he stuck to it, much to his detriment.

5. Trump congratulated himself for not bringing up Bill Clinton's marital infidelities.

Trump on Trade

In one of his final questions, Holt asked Trump what he meant when he said that Hillary Cinton didn't "look presidential," implying that Trump was alluding to the idea that a woman couldn't handle the job.

Trump tried to deny that there was any sexism in the statement and that he was instead saying that Clinton did not have the stamina for the job, a veiled reference to allegations that Clinton is not in good health.

Clinton answered the stamina claim by citing her admittedly robust travel schedule as secretary of state, but she did not let Trump off the hook for sexism.

“This is a man who has called women pigs, dogs and slobs, who has said pregnancy is an inconvenience to employers," Clinton said, going on to say that he even called a woman "Miss Piggy" at a beauty pageant.

Trump on infidelity

Trump denied that he said that and then replied, "I was going to say something extremely rough to Hillary, to her family, and I thought, 'I just can’t do it.'" Trump later revealed that the awkward comment was a reference to Bill Clinton's infidelities.

In sum, Trump tried to counter the attack that he was a sexist by praising his restraint in not using Clinton's husband's mistress against her.

Yikes, indeed.

TL;DR: Trump's big mistake? Talking about himself.

Trump's biggest mistake in this debate was his willingness to go into the weeds to attempt to correct the record on every accusation that Clinton made against him, even when he really had no good explanation. If there's been anything consistent in what's been a wildly erratic election year, it's that you don't want to be the center of conversation. When FBI Director James Comey said that Clinton acted "extremely careless" in her use of a private email server while she was secretary of state, Clinton's numbers took a nose-dive because her scandal was front and center.

Then, when Trump bizarrely attacked the parents of a Muslim soldier who died in Iraq, he took center stage and found himself plummeting, even trailing Clinton in reliably Republican states like Arizona and Georgia.

Finally, the race tightened once more after Clinton took a hit for her infamous "bad weekend" in which she insulted half of Trump's supporters as "deplorable" and was not forthcoming about her case of pneumonia.

Tonight, Trump made the mistake of letting the debate be about him. About his stance on Iraq. About his birther crusade. About his taxes. About his business record. One could easily imagine an alternate universe where Clinton was reeling from a debate centered on the State Department emails, the Clinton Foundation, and Clinton's honesty.

No doubt Trump will attempt to right that wrong in St. Louis when the candidates get together for the second debate on October 9th.

Trump also struggled to match Clinton's answers on policy questions. While Clinton was able to rattle off a laundry list of policies and demonstrate a nuanced understanding of the issues, Trump had trouble articulating anything specific, an indication that he had a tough time adjusting to a one-on-one debate after thriving in the 15-person battle royales of the Republican primary debates.

The initial CNN poll says Clinton won tonight. Will it matter? Time will tell.