(CNN) When Michael Bloomberg takes the 2020 debate stage for the first time Wednesday night, allegations of sexist and misogynistic behavior will loom over the former New York City Mayor.

They include claims from the 1990s that prior to a male colleague's wedding, Bloomberg told a group of female employees to "line up to give him a blow job as a wedding present"; that he would regularly direct comments like "look at that nice piece of ass" at women in the office; and that upon learning that a female employee was expecting a baby, he responded: "Kill it!"

Bloomberg, through his representatives, has denied making the "kill it" comment and other comments laid out in at least two lawsuits, but has also acknowledged that he has made comments that do not align with his values.

The renewed criticism comes as the 78-year-old is mounting an unconventional campaign for the White House, choosing to forego the four early states and targeting the delegates-rich Super Tuesday contests and beyond. The billionaire has already poured hundreds of millions of dollars into the race, blanketing the country with more than $400 million on television, radio and digital advertisements. Those efforts appear to be working for now: Bloomberg has risen in recent national polls, notably eating into support for former Vice President Joe Biden.

But as Bloomberg's candidacy gains traction, his decades-long record as a business titan and three terms as mayor of New York City is garnering fresh scrutiny, including his legacy of fostering the deeply controversial policing tactic of "stop and frisk." And his alleged offensive comments about women could make for particularly charged moments in light of the #MeToo movement.

Democratic Party leaders and allies are confronting uncomfortable questions about Bloomberg's past conduct, but there have not yet been widespread statements of condemnation against the former mayor. Further complicating matters is the fact that Democrats have been outspoken in calling out the numerous accusations of sexual harassment and assault made against Donald Trump. Trump has denied those allegations.

The Bloomberg campaign is responding to questions about his past behavior in part by highlighting his history of promoting women to senior roles both as a businessman and mayor.

Campaign chairwoman Patricia Harris said as a part of a lengthy statement: "In any large organization, there are going to be complaints -- but Mike has never tolerated any kind of discrimination or harassment, and he's created cultures that are all about equality and inclusion. Anyone who works hard and performs well is going to be rewarded, regardless of gender, race, sexual orientation or anything else."

A boy's club

CNN examined two lawsuits that paint a vivid picture of the billionaire as having allegedly condoned and promoted misogyny and sexism in the workplace.

Sekiko Sakai Garrison was a sales representative at Bloomberg LP until she was terminated in May of 1995, and she sued Bloomberg in 1997. The lengthy complaint detailed the many ways in which Garrison said Bloomberg and other male executives at the company sexually demeaned and harassed female colleagues. Bloomberg spokesman Stu Loeser said that Bloomberg "did not make any of the statements alleged in the Sekiko Garrison case."

In that lawsuit, the Bloomberg LP office was described in the suit as a boy's club where career advancement for women depended heavily on their "sex appeal." "Wearing short skirts was said by these male executives, and others, to be an advantage for promotion. Women who applied for sales positions were required to meet criteria of sex appeal," Garrison's complaint said. "Women sales persons who were less attractive or who were married were ridiculed and new mothers and recently married women lost lucrative portions of their sales territory, were denied business opportunities, had their pay cut and received inferior bonuses as compared to their male counterparts."

That culture of pervasive harassment stemmed directly from the man at the top of the firm, Garrison alleged.

According to her complaint, Bloomberg so frequently said the words "I'd f**k that in a second" in reference to women that it was shortened to "in a second." Bloomberg also uttered comments like, "That's a great piece of ass" in the presence of colleagues, she said.

Garrison laid out multiple allegations of Bloomberg directly targeting her. In 1993, Bloomberg purportedly said to Garrison: "You still dating your boyfriend? You giving him good blow jobs?

And when Garrison got engaged around that time, Bloomberg saw her ring and allegedly said: "What, is the guy dumb and blind? What the hell is he marrying you for?"

When Garrison eventually informed Bloomberg that she was pregnant in 1995, she alleged that he responded: "Kill it!"

"Plaintiff asked Bloomberg to repeat himself, and again he said, 'Kill it!' and muttered, 'Great! Number 16!' suggesting to plaintiff his unhappiness that sixteen women in the Company had maternity-related status," the complaint said. "Then he walked away."

The lawsuit has been previously been reported on by multiple outlets. A former Bloomberg employee, David Zielenziger, told the Washington Post in a story published over the weekend that he had witnessed Bloomberg's conversation with Garrison. That lawsuit was ultimately settled on undisclosed terms.

"In his testimony in the case, Mike said: 'I never said those words and there would be no reason to do so, it's ridiculous and an outrage," Loeser said. "Mike openly admits that his words have not always aligned with his values and the way he has led his life and some of what he has said is disrespectful and wrong."

Bonnie Josephs, a lawyer who initially represented Garrison, told CNN: "My experience of her complaint was that it was well-founded and that it was credible." Neal Brickman, a lawyer who represented Garrison after Josephs, did not respond to a request for comment.

'Feeling someone looking at me'

Mary Ann Olszewski, a former Bloomberg LP sales representative who worked at the firm from 1993 to 1995, sued the company and one of its then-executives whom she accused of rape. In a 1997 deposition, Olszewski said she was "regularly" on the receiving end of harassing looks from Bloomberg.

She said that on at least 20 occasions, she experienced "reaching up for things and feeling someone looking at me, turning and seeing Mike Bloomberg directly looking at my skirt going up and giving me a little look, like a sexual look."

Olszewski also claimed that Bloomberg often used crude language in the office. "Look at that nice piece of ass," Olszewski recalled Bloomberg saying about a colleague.

At one meeting, Olszewski alleged, Bloomberg openly disparaged a woman he was dating at the time, making a "condescending" joke about how "I need to be deaf, blind and dumb" to go out with her.

The Village Voice reported in 2001 on details of Bloomberg's deposition in this lawsuit (CNN was only able to obtain a part of the deposition). The media executive said, according to the Village Voice, that he would believe a rape charge only if it was backed up by an "unimpeachable third-party" witness.

Loeser, the Bloomberg spokesperson, told CNN: "It was a contentious deposition and this is not what Mike believes."

The Olszewski case was closed in 2001 after Olszewski's legal team missed a filing deadline . Olszewski's lawyer at the time did not respond to CNN's request for comment.

One former senior Bloomberg LP employee who worked closely with Bloomberg told CNN in an interview that both Bloomberg's behavior and the hostile work environment that Garrison and Olszewski described in the two lawsuits were consistent with what they also witnessed during their tenure at the company.

"When you're a woman who worked at Bloomberg, you had to look beautiful. You had to be gorgeous," said the former employee who spoke on the condition of anonymity. "If you were overweight, they would call you horrible names. It's mean stuff."

One such commonly used nickname that Bloomberg and his colleagues used, according to this ex-employee, was "SFU" -- abbreviation for "Short, Fat and Ugly."

This person also described Bloomberg's penchant for denigrating pregnant women in the office, including by making comments like, "I didn't get her pregnant, but I could have." When Bloomberg deemed a woman attractive, he would make remarks like, "I could have her any time," they said.

And those kinds of remarks are not just rooted in allegations from the distant past.

Bloomberg was described by one reporter as making crude remarks about women's looks when he was New York City's mayor.

And Bloomberg also raised eyebrows in late 2018 when in an interview with The New York Times , he said about allegations leveled against disgraced TV anchor Charlie Rose: "I don't know how true all of it is." Rose taped his namesake show at Bloomberg studios, and Bloomberg LP was named as a defendant in one of the lawsuits brought against the former host.

CBS and PBS fired Rose in November of 2017 after multiple women accused him of sexual harassment, which Rose has denied.

"We never had a complaint, whatsoever, and when I read some of the stuff, I was surprised, I will say," Bloomberg told the Times. "But I never saw anything and we have no record, we've checked very carefully."