We’re at a crucial point in the the 2020 Democratic presidential primary: two early voting states are behind us and two more — Nevada and South Carolina — lay ahead. Some candidates are skyrocketing in the national polls while other former frontrunners are swiftly dropping; needless to say, February has been intense.

Tonight, six Democratic presidential candidates faced off just days before the Feb. 22 Nevada caucuses, each trying to prove they can mobilize a diverse Democratic coalition. And although it’s the ninth DNC-sanctioned debate of the election cycle, a new face was on stage: Former New York City Mayor Michael Bloomberg.

The 78-year-old billionaire made the debate stage for the first time since the DNC ended its donor requirements. (He has pledged to self-fund his campaign and thus couldn’t qualify for previous debates.) Bloomberg has already spent more than $200 million dollars on television and digital advertisements, rapidly rising in the polls. Because he entered the race late, he’s decided to skip the first four voting states – Iowa, New Hampshire, Nevada, and South Carolina — and instead poured his resources into the Super Tuesday contests on March 3. Meaning that while he’ll appear in the Nevada debate, he won’t be on the ballot for the Nevada caucuses this weekend.

Former Vice President Joe Biden, former South Bend, Ind., Mayor Pete Buttigieg, Minnesota Sen. Amy Klobuchar, Vermont Sen. Bernie Sanders and Massachusetts Sen. Elizabeth Warren also appeared on stage. Warren and Biden — who were once thought of as front runners — need strong debate performances after coming in fourth and fifth in New Hampshire, respectively.

NBC, MSNBC and The Nevada Independent co-hosted the debate, which aired live from the Paris Theater in Las Vegas. Five journalists co-moderated: NBC anchor Lester Holt, NBC political director Chuck Todd, White House correspondent Hallie Jackson, Noticias Telemundo senior correspondent Vanessa Hauc and The Nevada Independent editor Jon Ralston.

Candidates had until 11:59 p.m. on Tuesday to get at least 10% in four DNC-approved polls or 12% in at least two early state polls (South Carolina and/or Nevada). Candidates with at least one delegate could also qualify. Tonight’s debate will be the third of four debates held by the DNC in early voting state, the last of which will be in Charleston on Feb. 25.

It’s been a long month for the Democrats. The first nominating contest of the election cycle, the Iowa caucuses, were a mess, and the Associated Press said it’s unable to declare a winner. Buttigieg and Sanders both came within striking distance of first place, and in the end Buttigieg received 13 delegates to Sanders’s 12. A little over a week later Sanders won the New Hampshire primary with 26% of the vote, though Buttigieg followed closely with 24% and Klobuchar came in third with 20%.

But Democratic voters in Nevada and South Carolina are much more diverse than in Iowa and New Hampshire, and candidates have yet to prove how they mobilize voters of color. Tonight, they’ll make their case to Nevada and the rest of the U.S.

Here are the biggest moments from the Feb. 19 debate:

Buttigieg vs. Klobuchar

Buttigieg and Klobuchar, who finished second and third in the New Hampshire primary, respectively, sparred throughout the night. Klobuchar was asked by moderator Vanessa Hauc how she planned to protect the DREAMers, and she responded that her plan was “to beat Donald Trump.”

Buttigieg countered, saying that Klobuchar needed to own her votes, and said that she voted to confirm the head of the Trump administration’s Customs and Border Protection who was one of the architects of the family separation policy, and that she voted to make English the national language. He then argued he had expert fighting for immigrants as mayor of South Bend, and ended his answer in Spanish. Klobuchar fired back, “I’m sorry not everyone can be so perfect as you. Let me tell you what it’s like in the arena.”

She said that she has opposed two-thirds of Trump’s nominated judges and said the official she confirmed was supported by another Democrat in the room and was “highly recommended by the Obama Administration.” She added she did not support “one bit” of those “draconian” policies and would repeal them in her first 100 days. She also added that she worked on multiple immigration reform bills in the Senate.“You’ve not been in the arena doing that work, you’ve memorized talking points,” she said to Buttigieg.

He responded that he has plenty of experience even though he’s never worked in Washington, and added that he’s used to “senators telling mayors that they don’t matter.”

Sanders defends himself on socialism

When asked about a recent NBC News/Wall Street poll showing that two-thirds of all voters were uncomfortable with a socialist candidate, Sanders responded by asking “what was the result of that poll,” pointing out that it also showed him in the lead.

Sanders said that America already is a socialist society, but that it’s only for the very rich and the poor are forced to deal with “rugged individualism.”“I believe in Democratic socialism for working people not billionaires,” Sanders said.

Bloomberg pushed back, saying Sanders is the “best known socialist” in the country, but also is a millionaire with three houses. Bloomberg did say that taxes should be raised on the rich and that he did that when he was mayor.Biden weighed in and said work needs to be rewarded and not just wealth. He said that the tax rate should be 28% for corporate America and added that the middle class is getting killed and the poor have no way of moving up.

Buttigieg was also asked about his previous praise of Sanders, and if he was now out of touch with other Millennials who accept Sanders’ version of socialism.Buttigieg said that he respects Sanders but was critical of the Vermont senator’s proposed healthcare plan that he said would raise taxes of anyone making over $29,000. Sanders countered saying that people will not have to pay premiums, deductibles or co-pays.

Bloomberg faces attacks over harassment allegations and NDAs

Bloomberg was asked about how multiple former employees have said his company is a hostile workplace for women and the former mayor himself has admitted to making sexually explicit remarks. “Should Democrats expect better from the nominee?” he was asked by moderator Hallie Jackson.

Bloomberg has been the subject of multiple lawsuits and allegations of sexual harassment in the workplace. The Washington Post reported, citing witness interviews and court appearances, multiple instances of offensive and sexists comments made by Bloomberg toward women in the workplace. Bloomberg denied the majority of the allegations, which go back decades, in depositions cited by the Post.

When asked, about these allegations during the debate, Bloomberg responded that he “has no tolerance for the kind of behavior that the #MeToo movement has exposed” and highlighted the fact that his foundation is run by a woman, he has a long career of employing women.

Warren swiftly jumped on the report. “I hope you heard what his defense was,” she said. “I’ve been nice to some women.” The Massachusetts senator then mentioned the fact that multiple former Bloomberg employees have signed Non-Disclosure Agreements (NDAs) after working for him, a tactic used by many powerful men who were exposed during the #MeToo movement. Then Warren asked Bloomberg if he would release those employees from their NDAs, and allow them to speak freely about their experiences if they wish too. Bloomberg responded that he had a “few” NDAs that didn’t accuse him of doing anything, except perhaps “disliking a joke [he] told.” Warren repeatedly asked Bloomberg how many NDAs there were, and he didn’t respond. She pressed him once again to release those women from their NDAs tonight, and he responded that those NDAs were an agreement made between two parties that wanted to keep the issue quiet, so he would keep it quiet.

Warren responded that it’s rather a situation of women being “muzzled” by the NDAs, and said the issue was not just an issue of Bloomberg’s “character” but is also an issue of electability. “We are not going to beat Donald Trump with a man who has who knows how many NDAs and the drip, drip, drip of stories of women who say they have been harassed,” she said.

Biden jumped in, and supported Warren by demanding Bloomberg release the women from their NDAs. He said it’s actually not an issue of women wanting the issue to remain private, but rather being paid by Bloomberg’s attorney to sign the NDA.

Bloomberg responded that he’s not going to “end the agreements because they were made consensually and they have every right to expect they will stay private.” “If they want to release it, then they should be able to release it,” Biden fired back.

Klobuchar addresses forgetting Obrador’s name

When pressed about not knowing the name of Mexico’s President during an interview earlier this week, Klobuchar said that it was a moment of forgetfulness that doesn’t represent what she knows about Mexico and how much she cares about the country.

“I made an error, I think having a President that maybe is humble and is able to admit that here and there maybe wouldn’t be a bad thing,” Klobuchar said.

She also said that she was the first person on the debate stage to show support for the Mexico-U.S.-Canadian trade agreement.

However, Buttigieg was quick to disparage Klobuchar, saying that she’s on the committee that oversees trade and should have known his name.“You shouldn’t trivialize that knowledge,” Buttigieg said. Klobuchar asked if Mayor Pete was calling her “dumb”. She defended herself and said that she has passed over 100 bills as a Senator and said that Mayor Pete lost his run for state treasurer in Indiana by over 20 points.

Warren came to the defense of Klobuchar and said that the criticism she is receiving is unfair.

“Let’s be clear, missing a name all by itself does not indict that you do not understand what is going on,” Warren said.

Bloomberg responds to questions on “stop-and-frisk”

When asked about the 2015 audio that resurfaced audio of Bloomberg saying most murder suspects in New York fit the same M.O. “male minorities, 16 to 25,” Bloomberg during the debate continued to apologize for the way the controversial “stop-and-frisk” policy “turned out.”

He said that his goal was to lower the murder rate, and that since there were 650 murders a year, he wanted to make sure people had the right to live. Bloomberg said he thought stop-and-frisk would help curtail the killings.

“It got out control, and when we discovered, I discovered, that we were doing many, many, too many stop and frisks, we cut 95% of it out,” Bloomberg said. He added that the crime rate did go down, but that they could not go out and stop people indiscriminately. Biden said that the reason stop-and-frisks slowed down was because then-President Barack Obama sent moderators there that said the practice must stop and that at the time, Bloomberg didn’t agree.

But in fact, the practice was scaled back after a federal judge in 2013 ruled stop-and-frisk violated the constitution, calling it “a form of racial profiling.” The NYPD in turn issued mandated that police officers have a justified reason to make a stop.

On stage, Bloomberg responded and said that he has apologized and that criminal justice as a whole needs to be fixed. “If we took off everybody off this panel that was wrong about criminal justice at some time in their careers there would be nobody else up here,” Bloomberg said.

Warren noted that Bloomberg has only apologized for how stop-and-frisk “turned out” and not what it was designed to do in the first place.

“It targeted black and brown men from the beginning,” Warren said of the policy that disproportionately affected Black and Latino men. “The apology has to start with the intent of the plan as it was put together.”

Buttigieg and Sanders spar on electability

The former South Bend, Ind., mayor and New Hampshire senator were neck-and-neck in the first two primaries, and at the debate, they were quick to make the case that the other would be the wrong candidate for the Democratic Party. Buttigieg argued that many Americans don’t see themselves fitting into the party of Bloomberg or Sanders, and cautioned against polarizing the party in either the progressive or moderate direction, presenting himself as the alternative.

”Let’s put forward somebody who actually lives and works in a middle class neighborhood,” he said. “Let’s put forward somebody who is actually a Democrat,” he added, a clear jab at Sanders who was registered as an Independent until he ran in the 2016 primary.

“We shouldn’t have to choose between one candidate who wants to burn this party down, and another candidate who wants to buy this party out,” he said, situating himself as the option in between Sanders and Bloomberg.

Sanders responded that he speaks to the “pain” of the “neglected working class,” arguing that Buttigieg “got the wrong word” when the former mayor called him “polarizing.”

Sanders said he aims to give a voice to people who are tired of growing economic inequality, and said “maybe it’s time for the working class of this country to have some power in this country, rather than your billionaire campaign.” Buttigieg accepts donations from billionaires, while Sanders does not.

The two went back and forth about who cared more about the working class, and Buttigieg brought up Sanders’ current tension with Nevada’s Culinary Union. The union has said it received threatening messages from Sanders supporters after announcing its opposition to Medicare for All.

Health care gets more debate time

Like clockwork, the crucial Democratic issue of healthcare came up early on in the debate.

Sen. Sanders was asked by Church Todd, “There are some Democrats that like you a lot but worry that this plan, Medicare for All goes too far and takes away private insurance. Are they right?”

“No,” Sanders predictably responded. “For 100 years, from Teddy Roosevelt to Barack Obama, this country has been talking about the need to guarantee healthcare for all people.”

He argued that despite spending twice as much as any other major country on earth, millions remain uninsured. Sanders then address the Nevada’s Culinary Workers Union, that has openly opposed Medicare for All. “I will never sign a bill that will reduce the healthcare benefits they have, we will only expand it for them, for every union in America, and for the working class of this country.”

Warren then attacked Buttigieg, saying his plan would leave millions unable to afford their healthcare. “It’s not a plan, it’s PowerPoint.” She then turned to Klobuchar, saying that her health care plan is only “two paragraphs” and likened it to a “Post-it.”

Buttigeg and Klobuchar were swift to defend their plans. Buttigieg said his plan would insure all Americans without kicking them of their insurances, and then hit back against Sanders: “This idea that the union members don’t know what’s good for them is the exact kind of condescension and arrogance that makes people skeptical of the policies we’ve been putting forward.” Klobuchar argued that her public option would reduce premiums for 12 million people and expand coverage for a smilier number. “It is a significant thing. It is what Barack Obama wanted to do from the very beginning,” she said.

Biden, who famously helped Obama whip votes for Obamacare in Congress, argued that he was “the only one who got anything done on healthcare.” When discussing health care, Warren returned to her message that she’s the candidate who “has a plan for that.” First, the Massachusetts senator criticized Buttigieg’s healthcare plan, arguing it only puts caps on premiums leaving the rest of a health care cost up to the American family.

Bloomberg then turned to the issue of health care, and said that he supported Obamacare back when he was mayor of New York City but felt it did not go far enough. He added that “the first thing we need to do is get back the White House.” Biden pushed back against Bloomberg’s characterization of his position, pointing out the fact that in 2010 he called Obama a “disgrace” that would do “absolutely nothing to fix the big health care problems.”

Candidates go at Bloomberg early

Candidates wasted no time going at Bloomberg over his policies as Mayor of New York City and allegations of sexual harassment in the workplace.

In his opening remarks, Sanders criticized Bloomberg for the impact the controversial policy widely known as “stop-and frisk” had on the Black and Latino community. Bloomberg responded by saying that there is no chance that Sanders can beat President Donald Trump in a general election.

“I don’t think there’s any chance whatsoever [that Sanders can win] and if he goes and is the candidate, we will have Donald Trump for another four years and we can’t stand that,” Bloomberg said.

Warren was equally critical and said Bloomberg is a “billionaire who calls women broads and horse-face lesbians.” She said Democrats will not win if a nominee who has a history of hiding his tax returns, harassing women and supporting racist policies.

“I’ll support whoever the Democratic nominee is but understand this, Democrats takes a huge risk if we just substitute one arrogant billionaire for another,” Warren said.

Klobuchar said she welcomed Bloomberg to the stage because she didn’t want him to hide behind his ads and was critical of the memo from his campaign that said certain candidates should get out of his way.

Bloomberg defended himself and said that he is not only the best candidate to beat Trump but would also be best equipped to run the country given his experience as Mayor of New York.

Michael Bloomberg makes his first debate appearance

Bloomberg has a lot to prove tonight. Even though he announced his candidacy in the fall, the former mayor missed the previous debates because of their donor requirements. Starting tonight, candidates no longer have to meet a donation threshold, opening the door for Bloomberg to appear on stage.

Tonight will be the first time many Americans see Bloomberg outside of his well-produced advertisements, and he’ll likely be on the defense. Candidates might take aim at his massive spending and wealth, as well as the fact that he jumped into the race too late for voters in the first four states to rule on his candidacy. Bloomberg is more wealthy than even many other billionaire, such as his fellow candidate Tom Steyer who did not make the debate. The former mayor is worth more than $64 billion and is the eighth richest person in the U.S., according to Forbes.

Warren and Sanders have been campaigning off Bloomberg for months, arguing his candidacy proves the corrupting power money has in politics. On Tuesday, Warren called him an “egomaniac billionaire” and compared him to President Donald Trump. Sanders has said he’s trying to buy the election. Moderate candidates will also go after him, given the threat he poses to maintaining their bases.

Bloomberg, meanwhile, will try to continued his momentum. A NPR/PBS NewsHour/Marist poll published Tuesday found he was polling second after Sanders with 19% of Democratic voters.

How will the results from New Hampshire and Iowa affect the debate?

Buttigieg and Sanders will also take some heat. After performing strongly in the first two states, they appeared to have been teed up as the front runners for the moderate and progressive wings of the party. But that can quickly change. Klobuchar did surprisingly well in New Hampshire after a strong debate performance; she’ll try and repeat that magic again in Nevada. And of course Bloomberg has quickly risen in the polls, having already passed Buttigieg nationally.

Given his lead in the polls and his recent win, Sanders might face even more attacks than Bloomberg. Eric Herzik, a professor of political science at University of Nevada, writes in an email that he “can see a scenario where Klobuchar and Buttigieg (with Biden also in the mix) go after Sanders on the electability issue, healthcare, [and even] on taxes.”

Warren may also break her détente with her friend and ally in an attempt to win back some of the progressive base. Although she has not typically attacked candidates in previous debates, she may feel she has to after coming in fourth in New Hampshire.

Biden will also be on the offensive. “I think at this point, the Biden campaign is not quite on life support but they’re in the ambulance,” Jacob Thompson, a professor of communications at the University of Nevada, Las Vegas who teaches a class on political debates, tells TIME. As Bloomberg makes his case to moderate voters, Biden will try his best to stop him.

One way Biden might go after Bloomberg is by bringing up race. Over the weekend he criticized Bloomberg for the NYPD’s policy of “stop and frisk” under his tenure, which many have argued amounted to racial profiling. Bloomberg’s past comments about women and gender might also raise some attention.

Thompson tells TIME that a few issues could get more attention because of Nevada’s diversity, namely immigration policy, policing, cash bail and housing discrimination.

Correction, Feb. 20

The original version of this story misstated which state-wide Indiana office Pete Buttigieg lost by 20 points. He ran for state treasurer, not senator.

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Write to Madeleine Carlisle at madeleine.carlisle@time.com and Josiah Bates at josiah.bates@time.com.