For the second time in as many weeks, Sen. Elizabeth Warren (D-MA) used the Democratic primary debate stage to take a hatchet to Mike Bloomberg’s record—delivering some brutal moments that could do lasting damage to the former New York City mayor’s rising campaign.

During Tuesday night’s debate in South Carolina, Warren and Bloomberg got into it early, when the CBS News moderators asked the Massachusetts liberal why she thought Bloomberg was the riskiest choice for the party.

After pointing out that Democrats shouldn’t trust the billionaire philanthropist—citing his financial support of South Carolina’s GOP Sen. Lindsey Graham, a liberal bogeyman—Warren laid into a weak spot for the former corporate titan in a Democratic primary: his company’s treatment of women.

Warren referenced news reporting about Bloomberg’s businesses that alleged women were treated unfairly and discriminated against—behavior that included sexist jokes and comments from Bloomberg himself. The most heated part of the exchange came when Warren referenced a claim in a Washington Post story that Bloomberg once told a female employee of his to terminate her pregnancy by saying, “kill it.”

“Categorically never said it,” said Bloomberg. “When I was accused of doing it, we couldn't figure out what she was talking about. But right now, I'm sorry if she heard what she thought she heard or whatever happened, I didn't take any pleasure in that.”

Warren also returned to the topic of the nondisclosure agreements that Bloomberg’s companies pushed, which made it harder for employees to speak about their experiences there.

“The Bloomberg corporations and Mayor Bloomberg himself have been accused of discrimination,” said Warren. “They are bound by nondisclosures so that they cannot speak. If he says there is nothing to hide here, then sign a blanket release and let those women speak out.”

Asked to respond, Bloomberg said it was “probably wrong” to make the jokes. If it bothered them, I was wrong, and I apologize. I'm sorry for that.” Noting that his company has released employees from their NDAs, Bloomberg went on to argue that Warren would never be satisfied with any concession.

“The trouble with this senator,” he said, “is enough is never enough.”

The two also sparred on issues around race, a central topic in the primary and in South Carolina, where black voters are the key Democratic voting bloc. Warren went after Bloomberg hard on racial discrimination and housing, referencing Bloomberg comments from 2008 in which he linked the downfall of redlining—a discriminatory real estate practice—with that year’s financial crash.

“While Mayor Bloomberg was blaming the housing crash of 2008 on African Americans and on Latinos, in fact, I was out there fighting for a consumer agency to make sure people never get cheated again on their mortgages,” said Warren.

Bloomberg bristled in response, and defended his record as mayor. “I’m sorry, but, unfortunately, she's misinformed on red lining… When you're talking about affordable housing, we created 175,000 units of affordable housing in New York City. And I listen to them, they're in Congress and they say they can't get it done, can't get it done. But if you change something like the president, they would. No, you have to learn how to work with both sides of the aisle, and then you can get stuff done.”

During last week’s debate in Nevada, Warren also went after Bloomberg over the environment at his business, drawing particular scrutiny on the NDAs. Her attacks on him were considered to be her strongest moment on a debate stage yet—and an early indicator of Bloomberg’s vulnerabilities—providing some much-needed energy to Warren’s candidacy.