She is simply described as the person who, aside from his two children, knows Bloomberg best. Their relationship is not new and it runs deep, but it isn’t bound by law or religion. Even at a time of greater equity within marriages, they have chosen not to partake.
They don’t bill themselves as “two for the price of one.” The presidency is Bloomberg’s dream. And if he achieves it, perhaps, she can just continue being Diana Taylor, which would mean that although she hasn’t shattered a glass ceiling, she has at least destroyed a suffocating archetype.
Taylor has been traveling the country and explaining to voters why they should pick Mike. Her argument begins with his experience as the three-term mayor of New York City, his philanthropic efforts on behalf of gun control and climate change, and the problem-solving skills that transformed him into a “real” billionaire. As for the warm, fuzzy stuff: His favorite dinner is Shake ‘n Bake chicken, he hates it when you move his stuff around, and he never watched his cameos on “Law and Order.”
But by the time Taylor wraps up her always brief remarks, the Republican turned Democrat has unleashed her free-form anxiety over the state of the union, and her message has become less about installing Bloomberg specifically and more about installing anyone — any Democrat who can beat President Trump.
Taylor, 65, and Bloomberg, 77, have been together for 20 years. They did not meet cute. They sat together in 2000 at a business luncheon where he was speaking. He was a billionaire but not yet a politician. He was a Democrat; she was still a Republican. She left early. That evening, they happened to be dining at the same restaurant. “He looked at me and came over and said, ‘Would you like to have a drink after this?’ ” Taylor said yes.
They’ve been together ever since, which means that she has been around to witness his political affiliations shift from Democrat to Republican to independent and back to Democrat, as well as his ever-growing presidential ambitions, which he first articulated during the lead-up to the 2008 race. “He is a man of incredible capabilities and resources. I’ve always thought that he’d be a really good president,” she says.
It’s lunchtime in New York on Martin Luther King Jr. Day, and Taylor is settled into a roomy booth in a corner of Aretsky’s Patroon, a clubby restaurant on the city’s East Side. Her wardrobe is all tasteful textures and earth tones: a moss-colored suede blazer that’s neatly buttoned, slim trousers the color of yams. It’s not what one might describe as power dressing as much as it’s old money attire. The power is understood. She has wielded a significant amount of it.
Her career began on Wall Street at the dawn of the masters of the universe era of the 1980s. She survived it unscathed. In 2003, Gov. George E. Pataki appointed her New York state’s superintendent of banks, a financial watchdog who protects the public when bankers run amok. She sits on a host of boards, including Citigroup and Sotheby’s. She considered running for the Senate seat now filled by Kirsten Gillibrand (D-N.Y.)
At the time, however, Bloomberg was mayor, and she didn’t want to come home to the townhouse the two still share on the Upper East Side and argue about the often conflicting interests of the city and the state over dinner. And besides, if she spent her weekdays in Washington, what would she do with her dogs, two labradors named Bonnie and Clyde? (They have since passed away, succeeded by Cody and Libby.)
“What was enticing about it was, I think I would have really enjoyed running,” she says. “You need to know what you stand for and what you want to do and what you want to accomplish. And you need to know what’s going on with the people that you would be representing because it’s a service job.”
“It is absolutely a service job,” she repeats, as if this fact has gotten muddled in recent years.
Taylor could be referred to in many different ways. And yet, the New York Post regularly called her Bloomberg’s “gal pal.”
“That one I hate,” Taylor says.
“I hate ‘girlfriend’ because it sounds so temporary,” Taylor continues. “It’s very junior high.” Partner implies that theirs is a business relationship; companion has shades of “the other woman”; consort is practically Victorian.
“Nobody’s come up with the language around what we are,” she says.
There’s the tendency to assume that an unmarried, childless woman is on her way to, in pursuit of, desirous of, marriage and children. Why isn’t Taylor married? She was married once and divorced. Why doesn’t she have children? “I never had kids because there was never anyone I wanted to have kids with.”
While wife and mother are two words that do not apply to Taylor, there are plenty others that do. “I define myself first and foremost as I’ve had a fairly successful career,” she says.
“I define myself by my family: my parents or my brother or sister and their families.”
“And then obviously, as Mike’s partner or whatever you want to call it,” she says. “And sort of a step- whatever for Mike’s children — friend, I guess.”
Taylor is taking these identities, this highly relatable independence, on the campaign trail, where her message is focused on lifting up women as individuals — not as marital appendages, nurturing multitaskers or a voting bloc of uteri.
“Her famous boyfriend may be the least interesting thing about her,” says Vogue editor Anna Wintour, who has known Taylor for years and welcomed her into the magazine’s famed “closet” when her social life went into overdrive as the city’s “de facto first lady,” as she was called.
“She’s intelligent, independent — and completely her own person. Michael is lucky to have her.”
Taylor is an introvert who says she enjoys campaigning. Campaigning is showing up for dinners where you thoughtfully order the local specialty but take little more than a bite. At roundtables, people unfurl stories of their struggles, and you become saturated with their pain. You stand empty-handed at the center of a cocktail party where everyone else sips wine and wait for you to dazzle them. But will they even remember what you said after all the free booze?
Taylor encourages everyone to listen to Bloomberg’s Greenwood speech about economic justice. She points out that he’s a longtime supporter of Planned Parenthood. Meanwhile, listeners try to suss out just who she is: Oh really, they’re not married?
“We women are killing our careers and I really respect how she’s her own woman but still stands beside him,” says London Lamar, 29, a state representative from Memphis and a Bloomberg supporter. “Especially down South, we’re under such pressure to have a ring on your finger and have children. And there’s nothing wrong with that, but it’s not everyone’s path.”
Two days after lunch in New York, Taylor is road-tripping through Tennessee, even though voters in this red state don’t go to the polls until March 3, Super Tuesday. Because Bloomberg entered the race too late to compete in states that vote earlier, he’s running a national campaign with special emphasis on the March primaries and caucuses.
Taylor’s stump speech isn’t a barn burner with a dramatic crescendo. Her voice is pitched low and calm. She doesn’t hack at the air with her hand or jab at it with her thumb. She stands with her arms loosely folded in front of her — narrow shoulders drawn back in studiously erect posture — as if she’s always slightly chilled.
“I’m tired of waking up every morning to some demented tweet. The number one objective we should all have is getting [Trump] out. And the way to do that is elect a candidate for the Democratic Party who can beat Trump,” Taylor says to a group of mostly young African American women at the black-owned restaurant Mahogany Memphis. “You all decide who that is. And we all need to get behind them.”
“I think it’s Michael Bloomberg,” she says. “I’m biased.”
Taylor listens more than she talks. She writes notes in a little journal. She doesn’t use notes when she speaks.
Candice Jones, a petite black woman with a cloud of dark hair framing her face, asks Taylor to explain Bloomberg’s thinking on the stop-and-frisk policing program in New York. Bloomberg has apologized for not recognizing its impact in minority communities.
“Kids were being killed on the street. In the short term, the way to solve that problem was to get guns off the street and that was the fastest way to do it,” Taylor says. “As time went on, he realized, talking to people, that stop-and-frisk had gone overboard and he cut it way back.”
“Yes, it was bad. It was horrible. It affected people’s lives in a very negative way,” she says. “But the reason he was doing it was to stop people from being killed.”
Her answer isn’t laden with statistics; she doesn’t have a heart-tugging story at the ready. “Diana gave a very legitimate response. He reacted to an immediate condition,” says Jones, 36, an executive committee member of the Shelby County Democrats. “Sometimes we react to issues because we want results.”
She describes Taylor as “relatable” — a squishy, fuzzy, often-repeated term. What makes this white baby boomer New Yorker relatable to Jones, a black millennial from Memphis?
“There was one moment when her grammar slipped,” Jones says with a smile.
Taylor is often described as tall. What people really mean is that she is significantly taller than Bloomberg, who is 5-foot-7, according to his campaign. She has layered dark hair and a willowy physique of the sort that women seek through barre classes but that only genetics can produce. When Taylor’s face is at rest, the echoes of a lifetime of broad smiles spread out around her eyes and across her cheeks.
Taylor grew up in Old Greenwich, Conn., which is the tonier section of the supremely tony Greenwich. Her father, E. Douglas Taylor, was an executive at Union Carbide. Her mother, Lois, was a teacher at Greenwich Country Day, the private school Diana Taylor attended from first through ninth grade. She spent a year at Milton Academy in Massachusetts then graduated from Greenwich High School and went on to Dartmouth College.
Her world was rarefied and white, and one might assume she is missing full knowledge of what it means to be black, brown or poor. She describes her upbringing as middle class but from the vantage point of a blue-collar clock-puncher, it reads as well-to-do.
When she was in Detroit, a predominantly black city, to talk with female entrepreneurs, at least one of the guests was expecting “a pinkie up” lunch, as Taylor recalled. She presumed, incorrectly, an encounter with a snob.
“I was was never really exposed to anybody who wasn’t just like me until, basically, I went to college. And then I came to New York. The first Jewish person I really came across was somebody I worked with after I graduated,” she says. “She invited me to go to a seder. I had no idea what it was.”
“One thing that I found is that everybody has an interesting story,” she says. “You just have to get there and build a trust with the person to get them to talk.”
In between the bullet points of her well-heeled life, there’s the story of an ambitious woman coming of age personally and professionally in spaces where misogyny was as common — and as uncommented on — as oxygen. She faced roiling tides of sometimes-toxic masculinity at Dartmouth, where she was in the second class of women, and there were few black or openly gay students.
“The guys, when they were in big groups, they could be really obnoxious,” she says. “One-on-one, they were great.”
“It was all built around the fraternity,” Taylor says of the school’s social environment, which was part of the inspiration for the 1978 film “National Lampoon’s Animal House.” “One of the things you learned was when to be somewhere and when not to be. You do not go to fraternity basements at two o’clock in the morning, for instance.”
“I absolutely loved it; but it was hard.”
After finishing Dartmouth in 1977 with a degree in economics, she decided to go to Columbia University for business school. Her parents, rooted in a “Mad Men” mentality, were not pleased.
“It was the first fight I had with my father,” she says. “ My father basically said, why are you going to business school? You’re just going to get married and have kids and you won’t use your degree. And it’s expensive,” Taylor recalls.
“We had a knockdown, drag-out fight, which was great. Yeah. In the driveway. My father said, ‘You’re on your own.’ So I financed it through student loans. I had two jobs,” she says. “So anyway, actually, it was a really good experience.”
“Anyway . . .” It’s a verbal tick, a way to ease out of a difficult subject, to refuse the temptation to navel gaze or complain. It’s a confident shrug: everything will be fine. “Anyway . . .”
She had a part-time job as an administrator at what was once NYU Lutheran Medical Center in Brooklyn. She worked in the evenings and after her shift ended around midnight, she would take the subway back to the one-bedroom apartment she shared with two other women on the Upper East Side.
“It was in a really bad part of Brooklyn; [the hospital] was on the way down to the docks in Red Hook,” she says. “That was terrifying.” It was the late 1970s and the city had barely survived a fiscal crisis. A blackout had sparked mass looting and violence. And the Son of Sam murders had terrorized residents. Anyway . . .
When Taylor began her career at Smith Barney, the company was thick with testosterone. One night she was typing at a secretary’s desk. “Morgan Murray, [Smith Barney’s head of public finance], came by and said, ‘I never want to see you typing again. You are an associate; you do not type.’ I said, ‘But I’ve got to get this done.’ He said, ‘Don’t type.’ ”
“Thinking back on it, that was really pretty amazing. He realized the women were secretaries and if you were a woman and you were typing, you’d be cast as a secretary — not as a professional.”
Taylor had faith that if she worked hard, she’d get ahead and for a while that seemed to be true. She was recruited by Lehman Brothers; she moved on to Donaldson, Lufkin & Jenrette, where she was a senior vice president and helped set up the public finance department.
“I found out that the guy sitting down the hall from me, who had the same title as I did and I did more than he did, his bonus was bigger than mine,” she says. “ And at that point, I got really angry.” Anyway.
She left the firm. It’s with that backstory of having been undervalued that she now chairs the board of the microlending nonprofit ACCION and the employment skills organization Hot Bread Kitchen.
“It could not have been easy to be a woman in that field at that stage,” says Michael Schlein, who worked at Smith Barney in the early 1980s and is now the president and CEO of ACCION.
“Did being a pioneering woman on Wall Street shape her views on empowerment? I don’t know what her motivation is,” Schlein says, “but I think her commitment is deep and sincere.”
Diana Taylor could use a drink.
In Memphis, she listened to the story of a pregnant woman who had been reassured at her doctor’s visit that her baby was fine only to have a stillbirth shortly thereafter. By lunchtime she was in Nashville, where she met with members of Moms Demand Action: For Gun Sense in America and spoke aloud the name of a man’s brother who was the victim of an unsolved shooting: Christopher. Taylor, who has a masters in public health, leaned in when a mother still grieving over her son’s shooting death explained how grief counseling isn’t covered by health insurance. The next morning, it was Knoxville where she heard a story of how the desperately hungry can be racist toward the very people trying to feed them.
But for now, it’s dinnertime in Nashville, and potential Bloomberg supporters, including several former Trump voters, are gathered at the Ainsworth restaurant. Everyone seems to be sipping campaign wine except Taylor, who is empty-handed but for her reading glasses. She has been listening all day. And really listening is exhausting. She meets and greets with a quiet voice that demands listeners lean in.
“I’m sort of a unique partner of a presidential candidate on a lot of different levels,” Taylor says. But “I think I have a pretty good idea of who I am at this point.”
Correction: This story originally stated that Taylor worked at St. Vincent’s Hospital. It was actually NYU Lutheran Medical Center, which is now part of NYU Langone Hospital-Brooklyn.