On Monday night, two of the most unpopular and diametrically opposed presidential candidates in recent history faced off at Long Island’s Hofstra University for the first of three presidential debates. In an election of historic firsts, Hillary Clinton sparred against Donald Trump for 90 minutes, moderated by NBC’s Lester Holt. The stakes couldn’t have been higher in what was one of the most anticipated first presidential debates ever, with polls showing the candidates almost evenly matched in battleground states, making it a race that is too close to call. Organized broadly under the themes chosen by Holt—“America’s Direction,” “Achieving Prosperity,” and “Securing America”—the floor was wide open in a battle to woo undecided voters and a younger generation who are leaning towards third-party candidates or sitting out the election altogether.

For Clinton, who has lost her lead in recent weeks, her challenge was to stand up to an unpredictable opponent without appearing contemptuous or condescending. For Trump, the overarching question was whether we would see the impulsive, unrestrained Trump who has largely campaigned on a script of bluster, jokes, and insults, or the Trump of the late campaign who has made an attempt at appearing serious and presidential.

What was also unique in this debate is the unprecedented level of scrutiny focused on Holt, who would have to overcome the specter of colleague Matt Lauer’s widely panned performance in the pre-debate candidate forum earlier this month. In this debate, perhaps more than any other, the question of whether to fact-check the candidates emerged as a primary concern, considering Trump’s predilection for factually inaccurate assertions and how little pushback he has faced on the veracity of his statements. Below are eight of the most notable moments of the night.

Donald Trump Thinks Exploiting the Housing Crisis Was Just “Business”

In response to the first question about the candidates’ views on the economy, Clinton quickly put the heat on Trump, accusing him of “rooting for the housing crisis.” She pointed to a moment in 2006, when Trump had said of a potential real estate market crash, “I sort of hope that happens because then people like me would go in and buy.”

Trump interrupted her to remark, “That’s called business, by the way.”

It was an impulsive admission that the millions who suffered through the massive housing crisis would surely not appreciate. But it was not a surprise, since, as The New Republic’s Clio Chang pointed out, Trump’s top economic advisor John Paulson raked in billions during the crash. Throughout the night, Clinton repeatedly questioned Trump’s business interests and ability. Combined with the questions about his refusal to release his taxes, Trump the businessman was a continued target for Clinton throughout the night.

Hillary Clinton Has Not Been Fighting ISIS Her Entire Adult Life

At one point, Trump attacked Clinton for posting her plan to defeat ISIS on her website. “You’re telling the enemy everything you want to do,” he said, to which he added that this would surely make General Douglas MacArthur upset. “No wonder you’ve been fighting ISIS your entire adult life.”

Clinton invoked the fact-checkers at this moment, and The New Republic’s Alex Shephard obliged, pointing out that Clinton was 52 years old when ISIS was established. Furthermore, as Clinton noted later in the debate, Trump has laid out nothing remotely close to a plan to address the threat of ISIS.  

Clinton Attacks Trump’s “Trumped-up Trickle-down” Economics

Trickle-down economics is popularly accepted to have been a failure. So it made tactical sense that Hillary Clinton would attempt to peg this connotation of failure to Trump’s proposed tax plan, which skews heavily toward benefiting the wealthy. And yet the secretary’s chosen phrase of “Trumped-up trickle-down” came off as contrived and too clever by half.

As The New Republic’s Nicole Narea wrote, “One of Clinton’s biggest potential pitfalls in the debates is to appear over-rehearsed and stilted.” This is an accusation that has plagued Clinton in the past, and the expectation was that this would be one of the things that her campaign team would edit out of her strategy. 

Trump’s Definition of Smart Business is Tax-Dodging 

When Clinton highlighted the possibility that Trump may have avoided paying millions of dollars in taxes, Trump couldn’t resist the urge to score a point. Avoiding income tax “makes me smart,” he declared with no shame for the wider connotations of a presidential aspirant who would sacrifice the interests of the citizenry to make a quick buck. 

Trump has built his identity on being a popular and successful businessman. It is part of the foundation for his promise to make America great again. But in his eagerness to uphold that reputation, he sacrificed his other identity as a populist who is fighting for the middle and working class.

Lester Holt, The Fact-Checker We Deserve

Despite much hand-wringing about whether Holt would fact-check Donald Trump at all, Holt did push back on the candidate in instances of blatant factual inaccuracies. One instance was when Trump again denied supporting the decision to invade Iraq, as Alex Shephard pointed out.

Additionally, central to Trump’s law-and-order argument tonight was the example of stop-and-frisk in New York. As The New Republic’s Laura Reston highlighted, Holt rightly pointed out the tactic was ruled unconstitutional in 2013 despite Trump’s protestations that “it worked very well in New York.”

Clinton Didn’t Hold Back From Calling Trump a Racist

As Holt opened the debate to questions about race in America, he turned to Trump’s long record of questioning President Barack Obama’s U.S. citizenship and his recent about-face on the issue. It was a question that Trump should have expected, yet he floundered in his response, first pinning the blame for the entire birther controversy on a former Clinton aide before painting himself as a heroic seeker of truth who only did the job that journalists wouldn’t do.

However, Clinton would not let him off so easily. She stated in unequivocal terms that Trump had “tried to put the whole racist, birther lie to bed. But it can’t be dismissed that easily. He has started his campaign activity based on this racist lie.” She even went further back to 1973, when Trump was sued by the Justice Department for discrimination, painting his entire career as one steeped in racism. Turning to the topic of President Obama, Clinton topped off her comments by borrowing the wildly popular phrase from Michelle Obama’s Democratic National Convention speech: “When they go low, we go high.”

Donald Trump Can’t Stop Lying About His Position on the Iraq War

It was a night of fact-checking Trump’s claims, and his early support for the Iraq War emerged as a key sore spot for the candidate, a point which Holt repeatedly pressed. Trump continued to claim that he has always opposed the war. But as Alex Shephard pointed out, he voiced support for the war in 2002, and only criticized it in 2004, well after the war had already begun, when it had become the target of protest and opposition. Too little too late, in other words.

Trump’s dogged insistence that he has always opposed the war, despite all evidence to the contrary, is perhaps meant to give him the kind of leverage it gave Obama when he was running for president in 2008. Except, of course, in Trump’s case, it is simply not true. Nor would it be sufficient to prove that he has the foreign policy mettle to be commander-in-chief. To Holt’s credit, this is a point on which he simply would not give Trump a pass, perhaps learning from the outcry that followed Matt Lauer’s silence on the topic.

Donald Trump Went on a Sexist Rant

Things really unraveled for Trump when Clinton brought up his many past sexist comments. As Alex Shephard wrote, “Once again, Trump took the bait and went on an extended rant about how those comments were justified—Rosie O’Donnell had it coming!” Trump then came close to bringing up Bill Clinton’s infidelity, before landing on the claim that not bringing it up made him not sexist.