“It was 30 years ago, get over it,” Michael Bloomberg’s girlfriend, Diana Taylor, told CBS after a Women for Bloomberg event in Texas. She was referring to the alleged “locker-room talk” that Bloomberg used freely in the workplace in the ‘80s and ‘90s, and the nondisclosure agreements that former employees signed, ensuring that whatever happened at Bloomberg LP stayed at Bloomberg LP. After receiving public pressure from Senator Elizabeth Warren to release three former female employees from their NDAs, Bloomberg did so. Taylor remains dismissive.

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“In none of them was he accused of doing anything, saying something nasty to a woman,” Taylor said. “That is not who he is. Life has changed. I grew up in that world. It was a bro culture.”

But the bro culture that Bloomberg—presidential candidate, businessman, and former New York City mayor—was entrenched in defined the allegations that have followed him throughout his professional career. In fact, magazines and newspapers were eager to publish salivating profiles of the profane and prolific billionaire, enabling and validating a culture in which making crass comments at pretty women in one’s employ was just part of the game. The lawsuits against Bloomberg that followed were less glamorous, but Bloomberg remained impervious to accusations that he was a sexual predator and flagrant harasser, and continues to deny these accusations today.

But it’s tough to deny patterns, and there’s a clear pattern in the decades-long allegations of discrimination, dismissiveness, and provocation from Bloomberg. Here is a brief timeline of Bloomberg’s creepiest hits, as documented from magazine profiles, lawsuits, and interviews Bloomberg probably wishes never happened.

1990: The Portable Bloomberg

In 2001, New York magazine columnist Michael Wolff acquired a book called The Portable Bloomberg: The Wit and Wisdom of Michael Bloomberg. Dated February 14, 1990—Bloomberg’s 48th birthday—the book is dedicated to “President of Bloomberg Financial Markets, the Greatest Company in the World.” The sycophantic slobbering continues in the introduction which begins, “Yes these are actual quotes. No, nothing has been embellished or exaggerated. And yes, some things are too outrageous to include.” It’s a wonder what had to be edited out of this collection of Bloombergisms because the ones that were included were bad enough.

CHARACTERIZATION OF A COMPETITOR:

“Cokehead, womanizing, fag.”

EVERYDAY ACTS:

[...]

The three biggest lies are: the check’s in the mail, I’ll respect you in the morning, and I’m glad I’m Jewish.

[...]

“She’ll be the first one called into the courtroom”

ON MERRY OLD ENGLAND:

The Royal family—what a bunch of misfits—a gay, an architect, that horsey faced lesbian, and a kid who gave up Koo Stark for some fat broad.

ON WOMEN:

If women wanted to be appreciated for their brains, they’d go to the library instead of to Bloomingdale’s.

[...]

I know for a fact that any self-respecting woman who walks past a construction site and doesn’t get a whistle will turn around and walk past again and again until she does get one.

WHENEVER HE’S TOLD AN EMPLOYEE IS GETTING MARRIED:

“Are you pregnant?”

“Male or female?”

ON BEING ASKED TO NAME A SPORT THAT DOESN’T USE BALLS:

“Lesbian sex”

Bloomberg spokesman Stu Loeser told the Washington Post, “Mike simply did not say the things somebody wrote in this gag gift, which has been circulating for 30 years and has been quoted in every previous election Mike has been in.” But he added that Bloomberg “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.”

1993: New York Profile of Michael Bloomberg

Published in the November 22, 1993 issue of New York magazine, Rebecca Mead’s sweeping profile of businessman Bloomberg includes a photo of the man in rollerblades and a reminder that Bloomberg is a sex pest (who makes terrible jokes about black people to boot):

“Walking around his domain, Bloomberg exercises a certain droit du seigneur: getting one of his senior managers to hold up a trash can while he tosses a Cheez-Its packet into it from across the room (‘I could play for the Knicks if I ever grew up to be seven foot one and black,’ he cracks); commenting on the attractions of the younger women in the office, a habit for which he is notorious. (‘She is the reason all the young programmers come in early and stay late,’ he says, looking at a dark-haired girl walking to her desk. ‘She comes in in a different outfit every day. I don’t know where she gets the money, because she doesn’t make a lot.’)”

1996: John Hopkins Magazine, November ‘96 Edition

This interview with Bloomberg doesn’t veer into predator territory, but there’s mention of Bloomberg’s womanizing and the ease with which it is brought up in other profiles:

Bloomberg—who pronounces his name closer to Blumberg— has a reputation for impatience and profanity, but today he’s relaxed and mostly clean spoken. He must enjoy talking to reporters about guy stuff like rollerblading, pretty women, and flying airplanes, because few stories about him are without a paragraph or two of that sort of thing.

1996-1997: Sekiko Sakai Garrison v. Michael Bloomberg and Bloomberg, L.P.

In 1996 and 1997, four women filed lawsuits against Bloomberg LP alleging sexual harassment and discrimination. Of the four, the case of Sekiko Sakai Garrison is the most notorious and documents several acts of misconduct from 1989 to 1995. The allegations ranged from Bloomberg encouraging women employees to wear provocative clothing to improve their chances of scoring promotions to the alleged rape of Bloomberg employee Mary Ann Olszewski by a Bloomberg manager Bryan Lewis.

The following is an abridged version of Bloomberg’s actions, according to the suit, including the infamous moment Bloomberg allegedly responded to Garrison’s pregnancy announcement with, “kill it!”:

  • “Upon information and belief, in 1989, when a male company salesperson was getting married, Bloomberg said to the female salespeople, “All of you girls line up to give him a blow job as a wedding present.”
  • “Upon information and belief, in October 1989, Bloomberg was unhappy with the outcome of a business meeting. He said to a newly-hired female Company salesperson, “If [the clients] told you to lay down and strip naked so they could fuck you, would you do that too?” He repeated similar words or substance at frequent intervals throughout the period of plaintiff’s employment.”
  • “...A female employee heard Bloomberg say, ‘Sekiko...[I’d do her] in a minute!’ as he stared at Garrison in her running shorts.”
  • “Upon information and belief, in the summer of 1992, hearing that a female Company salesperson had become pregnant, Bloomberg became very angry and said to her, ‘For Christ’s sake! What the hell did you do a thing like that for?’”
  • “In 1993, Bloomberg saw a newly-hired older female Company employee with an overweight male Company salesperson. Pointing to these individuals, Bloomberg asked Garrison, ‘If you had to, would you rather do THAT or THAT?’”
  • “In or about March 1993, Bloomberg asked Garrison, in the presence of a male Company salesperson who knew Garrison’s boyfriend, ‘You still dating your boyfriend? You giving him good blow jobs?’
  • “Upon information and belief, in or about July 1993, Bloomberg heard that a female Company salesperson, who had just had a baby, was having difficulty finding a nanny. He yelled loudly at her, in the presence of a large group of employees, ‘It’s a fucking baby! All it does is eat and shit! It doesn’t know the difference between you and anyone else! All you need is some black who doesn’t even have to speak English to rescue it from a burning building!’”
  • “In February of 1994, Bloomberg saw Garrison’s engagement ring and said, ‘What, is the guy dumb and blind? What the hell is he marrying you for?’ A week later, in response to Garrison’s having wished him a happy birthday, Bloomberg said, ‘Still engaged? What, is he THAT GOOD in bed, or did your father pay him off to get rid of you?’”
  • “In or about the spring of 1994, Garrison was having a business conversation with a male fellow employee. Bloomberg walked by and interrupted their conversation in order to say, ‘That is one great piece of ass. You must be a great fuck.’ As he said this, Bloomberg was staring at the male employee’s girlfriend—who was also employed by the Company—as she entered an elevator some distance away.”
  • “In the spring of 1994, in Garrison’s presence, Bloomberg gestured to another female salesperson, who was a friend of Garrison’s. ‘What do you think about THAT?’ Bloomberg asked Eccelston. Bloomberg answered his own question by saying, ‘Great legs, but not my type.’ Then, referring to the female salesperson’s thin, short-haired female assistant, Bloomberg said, ‘THAT would be like fucking a guy.’”
  • “In or about the summer of 1994, clients in Mexico were not getting good service due to poor telephone line connections. Bloomberg commented, ‘I don’t give a shit about those Mexican jumping beans. They are all hung up about the Alamo anyway.’”
  • “In July of 1994, referencing a specific outfit Garrison was wearing, Bloomberg said, ‘Don’t like the dress. Your ass looks huge in it.’ Bloomberg had made this exact comment to Garrison on numerous occasions, throughout the term of her employment, whenever she was wearing a new outfit.”
  • “In July of 1994, Bloomberg saw Garrison return from lunch with a Tiffany shopping bag. ‘You ARE a real Jap!’ he said to her.”
  • “On December 16, 1994, before the Company Christmas party, Bloomberg directed Garrison’s attention to a young female company employee who had just changed into a cocktail dress, as she exited the women’s room. ‘If you looked like THAT,’ he said to Garrison. ‘I would do you in a second.’”
  • “Upon information and belief, in March 1995, upon hearing that a female Company salesperson had become engaged, Bloomberg held out his hands at a relatively large distance from one another, and asked her, ‘What, is he THIS BIG that you have to have him every day?’ After having said this, Bloomberg stomped away.”
  • “Upon information and belief, from the time Olszewski was employed at Bloomberg LP until May 1995, Bloomberg repeatedly positioned himself so he could peer up her skirt or dress whenever she stooped or bent down to pick up something from the floor, or when she reached to get something from an overhead shelf or cupboard. Bloomberg behaved similarly to plaintiff and other women throughout the term of plaintiff’s employment. He would often ask other male employees to participate in this inappropriate behavior.”
  • “On April 11, 1995, at approximately 11:20 a.m., Bloomberg was having a photograph taken with two female Company salespeople and a group of N.Y.U. Business School students, in a company snack area. When Bloomberg noticed Garrison standing nearby, he asked, ‘Why didn’t they ask you to be in the picture? I guess they saw your face.’ Continuing his penchant for ridiculing recently married women in his employ, Bloomberg asked plaintiff, ‘How’s married life. You STILL married?’ Garrison responded that her marriage was great and was going to get better in a. few months: that she was pregnant, and the baby was due the following September. He responded to her ‘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. Then he walked away.”

In a deposition, Bloomberg admitted that he said he would “do” Garrison, but claimed he meant “do” as in have a relationship with her. In 2001, Bloomberg and Garrison settled with no admission of guilt by Bloomberg.

1999: Wired Profile

The following Bloomberg quote—in which he brags about his hot blonde daughter—could easily be mistaken as a quote from President Trump.

“My daughter is tall and busty and blonde,” Michael Bloomberg is telling a table of Boston College graduates. “We went to China together. And what’s a 16-year-old going to do on a business trip?” He pops another carefully buttered piece of bread in his mouth. “So I got her dates in every city in China.” Remembering that I’m also at the table, he glares in my direction. “That’s off the record!” he barks. It’s typical Mike Bloomberg, wanting to have it both ways: imperious man of the people, coarse billionaire, earthy business leader, accessible control freak.

1999: New York Times Profile of Bloomberg LP

Bloomberg’s “locker room talk” is still given a mention in this New York Times piece (emphasis mine):

Like the system he built, Mr. Bloomberg is enormously complex. He is generous: The company pays well, and he is an active philanthropist. He is also an obsessive worker, and numerous employees complain of a punishing work schedule. He has been aggressive in hiring women, but is not shy about using brusque sexual language in the office. Though he can be tough in pushing longtime associates aside, he is slow to dismiss anyone.

And here’s what he said about those pesky lawsuits:

“All three of their lawyers called up and said, ‘If you give us cash, we’ll go away,’” he said. “As far as I am concerned, that is out-and-out extortion, and I think companies caving in to that sort of thing are making a terrible mistake. And we will go and fight all three of these. And I, in my heart of hearts, believe that we have done nothing wrong.’’

2001: Australian Broadcasting Company Interview

In 2001, the Australia Broadcasting Company highlighted Bloomberg’s mayoral run. The lion’s share of the piece highlights Bloomberg as a go-getter, eager to change New York for the better and willing to spend an early morning shaking hands with people in the Bronx (the Bronx!) to do it. But toward the end comes this slightly skeevy anecdote:

GRAHAM DAVIS: Much is made here of your single man about town status.

MICHAEL BLOOMBERG: Oh.

DAVIS: Indeed, you once described your life as a wet dream.

BLOOMBERG: I saw that in the paper, I’m not sure I said that but—

DAVIS: It does sound good.

BLOOMBERG: Suffice it to say I was very happily married to a wonderful woman for 19 years, we have two children together, she is still one of my best friends. I’ve been divorced for seven or eight years and I lead an active social life would be a nice way to phrase it.

This was followed by men who know Bloomberg debating whether Bloomberg is a ladies’ man or simply a womanizer. Bloomberg was mayor from 2002 to 2013.

2007-2011: Equal Employment Opportunity Commission Lawsuit Against Bloomberg

In September 2007, a class-action lawsuit on behalf of 78 women was filed against Bloomberg LP claiming the organization “systematically discriminated against mothers and pregnant women by reducing their pay, demoting them or excluding them from important meetings.” Although Bloomberg was no longer responsible for day-to-day operations at the time when the discrimination was alleged to have taken place—February 2002 to March 2009—the suit claims that Bloomberg himself is “responsible for the creation of the systemic, top-down culture of discrimination.”

Given Bloomberg’s alleged statements about pregnant employees in the Garrison suit, this claim is not far fetched. But in 2011, Judge Loretta A. Preska dismissed the suit, citing insufficient evidence.

Preska wrote: “A female employee is free to choose to dedicate herself to the company at any cost, and, so far as this record suggests, she will rise in this organization accordingly. The law does not require companies to ignore or stop valuing ultimate dedication, however unhealthy that may be for family life.”

2008: Bloomberg’s Celebrity Apprentice cameo

Bloomberg acts like he’s President Trump’s nemesis now, but the two were friendly for years, on and off the golf course. Bloomberg appeared on Trump’s reality show The Apprentice in 2004 and Celebrity Apprentice in 2008. In the ‘08 cameo, Bloomberg helped judge a battle of the sexes hot dog contest.

From Buzzfeed News (emphasis mine):

... Bloomberg — with Trump, Ivanka Trump, and Donald Trump Jr. in tow — walks up to a hot dog cart staffed by cast members of Celebrity Apprentice while dramatic music plays in the background.

“This is our great mayor,” Trump says, introducing Bloomberg to the first team of celebrities, which included former White House official Omarosa Manigault Newman, who were selling hot dogs as a part of a competition between men and women.

“As the number one frank-ophile in the city, I’m supposed to see if you can cut the mustard,” Bloomberg told the team of women before biting into a hot dog.

“I can’t tell whether these are better or worse than the one the men are selling until I have a hot dog with the men. But I can tell you without seeing the men — you look better,” he told the women.

The women cheered.

2013: New York Profile of Christine Quinn

In 2013, Christine Quinn was the first openly gay Speaker of the New York City Council with dreams of succeeding Bloomberg as mayor. Quinn eventually lost the Democratic primary to current New York City Mayor Bill De Blasio, but a profile of her in New York magazine from January of that year includes a grimy nugget about Bloomberg that sounded just like businessman bro Bloomberg of the ‘90s. Here’s what Quinn witnessed at a holiday party (emphasis mine):

Later in the evening, the host interrupted me to point out that the mayor himself had just arrived. Did I want to meet him? Sure. My friend and I followed the host over, shook Bloomberg’s hand, and my friend thanked him for his position on gun control. Without even acknowledging the comment, Bloomberg gestured toward a woman in a very tight floor-length gown standing nearby and said, “Look at the ass on her.”

And then, there’s Bloomberg with fashion advice:

...We got to talking about fashion and bargains, and it was obvious to me that this was a conversation I would never be having with a male politician. Then [Quinn] said, “The mayor is going to yell at me when I get out of the car because I have flat boots on. The mayor has no use for flat shoes.” Really, I said. Why would he care? “I was at a parade with him once and he said, ‘What are those?’ and I said, ‘They’re comfortable,’ and he said, ‘I never want to hear those words out of your mouth again.’” Everyone in the vehicle, including the security detail in the front seat, cracked up. “He likes me in high heels. Let’s see how long it takes before he notices.” She scrolled through her BlackBerry. “Another big thing with the mayor, when I am rooting … like, the couple of days a week before I need to get my hair colored, he’ll say, ‘Do you pay a lot to make your hair be two colors? Because now it’s three with the gray.’ And I’m like, ‘Did you wake up being this big of an asshole? Or did it take, like, all day to ramp up to it to be able to insult me like that?’”

Quinn brushed off the jabs and assured that she had a good rapport with Bloomberg, that she prioritized having a productive working relationship over a combative one.

2016: Transmisogyny at Oxford

Bloomberg’s 2020 presidential run has unearthed a slew of footage of Bloomberg talking at prestigious conferences about how stop-and-frisk is good and—apparently—how average Americans can’t comprehend trans rights.

In December 2016, Bloomberg spoke at an event at Oxford University about appealing to those with differing politics. Post-Brexit and post-Trump’s election, there was plenty to talk about on that front. But perhaps Bloomberg wasn’t the best one to speak to this challenge. He described himself and the attendees as the “intelligentsia, “and suggested that they are simply out of touch with everyone else, who values what he called “the rights of society comes first” over the “right of the individual.” He used this argument to explain why people in the Midwest—in other words, people who are not of the intelligentsia class—just can’t get with trans rights... which he reduced to “some man wearing a dress.”

“If you want to know if somebody is a good salesman, give him the job of going to the Midwest and picking a town and selling to that town the concept that some man wearing a dress should be in a locker room with their daughter. If you can sell that, you can sell anything. They just look at you and they say, ‘What on Earth are you talking about?’”

2019: Transmisogyny, Redux

At another pretentious forum in March of 2019—this time, hosted by the Bermuda Business Development Agency—Bloomberg implied that presidential candidates dedicating ample time to discussing transgender protections are losing average Americans.

“If your conversation during a presidential election is about some guy wearing a dress and whether he, she, or it can go to the locker room with their daughter, that’s not a winning formula for most people,” Bloomberg said.

A Bloomberg campaign spokesperson told Buzzfeed News that Bloomberg is a trans advocate, noting his implementation of a transgender civil rights bill as mayor, the comprehensive health care that his trans employees receive, and his dedication to ending violence against transwomen. They did not respond to criticism of Bloomberg’s use of “it.”

Staff writer, mint chocolate hater.

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