After spending hundreds of millions of dollars on campaign advertisements, billionaire Michael Bloomberg joined the other Democratic candidates on stage.
He must be the first candidate ever to pay such a princly sum to be roughed up so badly.
Former mayor Michael Bloomberg only met the polling qualifications on Tuesday after the Democratic National Committee changed the rules in January for appearances on the debate stage.
The rule change helped Mr Bloomberg, who is boosting their standing in polls by large volumes of money, to debate.
With all candidates vying for relevance apart from Senator Bernie Sanders, here are some of the best quotes of the night, many of them aimed squarely at the New York billionaire.
Bloomberg on Senator Sanders chances of becoming president
"If he goes and is the candidate, we will have Donald Trump for another four years and we can't stand that."
Warren welcoming Bloomberg to the debate
Elizabeth Warren welcomed Mr Bloomberg to the stage in a rhetorical fashion unseen in the Democratic debates.
"I'd like to talk about who we're running against — a billionaire who calls women 'fat broads' and 'horse-faced lesbians,' and no I'm not talking about Donald Trump. I'm talking about Mayor Bloomberg."
Warren on Bloomberg's record
“Democrats are not going to win if we have a nominee who has a history of hiding his tax returns, of harassing women, and of supporting racist policies like redlining and stop and frisk... Democrats take a huge risk if we just substitute one arrogant billionaire for another.”
Bloomberg asked about past comments and complaints from women
"We have very few nondisclosure agreements. None of them accuse me of doing anything other than maybe they didn't like a joke I told."
“I have no tolerance for the kind of behavior the #Metoo movement has exposed. Anybody that does anything wrong in our company, we investigate it, and if it's appropriate, they're gone that day.”
Warren's response to Bloomberg's answer
"He has gotten some number of women — dozens, who knows? — to sign nondisclosure agreements both for sexual harassment and for gender discrimination in the workplace. So Mr Mayor, are you willing to release all of those women from those nondisclosure agreements? So we can hear their side of the story?”
Cheers and applause followed.
The billionaire has had 64 separate lawsuits from women and organisations over sexual harassment.
Former vice president Joe Biden's response to Bloomberg's answer
“All the mayor has to do is say ‘you are released from the nondisclosure agreements.’”
Mr Bloomberg declined to release the women from their agreements.
Nondisclosure agreements are essentially contracts between individuals or an individual and a company or organisation which often bar people from speaking publicly about their experiences and observations with a person, company or organisation.
Warren on Bloomberg's comments on the 2008 housing crash
"When Mayor Bloomberg was busy blaming African-Americans and Latinos for the housing crash of 2008, I was right here in Las Vegas, just a few blocks down the street holding hearings… Banks…were taking away homes from millions of families," she said, referencing Mr Bloomberg's past comments on "redlining".
Redlining was the systematic denial of various services to residents of specific, often racially associated, neighborhoods or communities. Mr Bloomberg has said that when that policy ended, it contributed to the housing crash in the US in 2008.
These lending practices pushed disproportionate shares of black and Latino homeowners into foreclosure, according to the Center for Responsible Lending.
Bloomberg's answer to his controversial stop-and-frisk policy in New York
"Well, if I go back and look at my time in office, the one thing that I'm really worried about, embarrassed about, is how it turned out with stop-and-frisk."
He added that he believed his first responsibility as mayor was to "give people the right to live" and cut down on murders.
"Stop-and-frisk got out of control. And when we discovered, I discovered, that we were doing many, many, too many stop-and-frisks, we cut 95 per cent of it out.”
This was misleading as the practice was scaled back significantly thanks to a 2013 federal court order declaring the policy unconstitutional, not Mr Bloomberg’s change of heart.
Bloomberg on Bernie Sanders' policies
Mr Bloomberg tried to tout his capitalist credentials over Mr Sanders comparing the senator's policies to "communism".
"We're not going to throw out capitalism. We tried that, the other countries tried that — it was called communism — and it just didn’t work."
Mr Sanders' response
“Let's talk about democratic socialism. Not communism, Mr Bloomberg. That's a cheap shot ... We are living in many ways in a socialist society right now. The problem is, as Dr Martin Luther King reminded us. We have socialism for the very rich. Rugged individualism for the poor.”
Applause rang out.
“When Donald Trump gets $800 million in tax breaks and subsidies to build luxury condominiums, that's socialism for the rich.
“We have to subsidise Walmart’s workers on Medicaid and food stamps because the wealthiest family in America pays starvation wages, that's socialism for the rich."
What happened when someone Googled Democratic debate
“What a wonderful country we have. The best-known socialist in the company happens to be a millionaire with three houses. What did I miss here?”
Pete Buttigieg on the choice between Sanders and Bloomberg
“Most Americans don’t see where they fit if they’ve gotta choose between a socialist who thinks that capitalism is the root of all evil and a billionaire who thinks that money oughta be the root of all power.”
Sanders responding to Buttigieg's criticism on being divisive
“Unlike some of the campaigns up here, Pete, I don’t have 40 billionaires funding my campaign coming from the pharmaceutical industry and Wall Street. What we do have is six million contributions from 1.5 million people averaging $18.50 a contribution.”