It was a sunny September afternoon at the mayor’s house on East 79^th street and Diana Taylor was talking to the two boisterous Laborador retrievers that she shares with her boyfriend, Mayor Michael Bloomberg. “Yes!” she said, in a soothing voice the “Bonnie” and “Clyde” seemed to appreciate, “I’m talking about you!”

She had been describing her early morning hour-and-a-half walks with the dogs (which she bought for the Mayor four years ago) and extolling the virtues of Central Park in that sort of breathless-but-genuine tone that all New Yorkers adopt when speaking appreciatively about Things That Also Impress The Tourists. “Central Park is the most amazing gift,” she said. “It’s incredible. You find new spots, new people, new friends for the dogs. I love going to parks.”

But she wasn’t as bubbly as the sentiment would suggest. She erupted in a rare peal of laughter—“Oh my god, that was hilarious!”– only when asked about the Mayor’s Spanish speaking skills and the parody Twitter account @elBloombito, which exhorted New Yorkers during Hurricane Irena to “no looto el bodaga! Esta es Nuevo Yorko!” (She explained his technical proficiency despite abysmal pronunciation: he’s an engineer; they are very technical.)

As we sat at small table next to the kitchen, she spoke softly but directly, carefully considering everything she was saying.  A tall, charismatic figure who often appears to tower over her high-profile partner at public events, her demeanor was warm but professional.

And it makes sense. Until 2000, when she was seated next to the Mayor at a Citizens Budget Commission event, Ms. Taylor’s career was the most recognizable facet of her public identity. If her tone seems professional—comforting in one sense, and perhaps a bit over-polished in another–it’s because it’s the mode in which she’s accustomed to operating.

Before she met the Mayor, Ms. Taylor had occupied several high profile job positions in both the public and the private sector and was divorced, with no children.

She still holds several high profile positions and is still divorced with no children, but it’s probably fair to say that her day-to-day life now has several added dimensions that weren’t there before. Her social life is determined in many ways by the schedule of her partner and nights out (downtown for events, Harlem for dinner at the Red Rooster) are now routinely documented by photographers.

And of course this means Ms. Taylor is being scrutinized in ways she previously wouldn’t have expected.  Her fondness for tailored, elegant clothing has been noted in various fashion pages and her favorite designers (Oscar de la Renta, Carolina Herrera, Ralphs Rucci and Lauren, natch) have been catalogued for the public. But  the look isn’t entirely comfortable for the first girlfriend. Our photographer assumed that her consistent, well-put together look was the work of a personal stylist and Ms. Taylor seemed taken aback by the idea.

“My what?” she said, laughing. Stylist? “You’re talking to her!”

 

But, she acknowledged, she did have her own personal style. “I like simple, not too frilly, tailored.” And then, with a tiny sparkle of calculation: “And my favorite designers are New York City based designers. So that makes it easy because they’re mostly tailored and elegant clothes.”  We pointed out that the Greenwich native’s taste in clothing seemed very, well, Greenwich-ian. “Yeah, I know,” she said. “[But] let me put it to you this way: I basically wore overalls all the way through college. I mean, you just try and present yourself as being neat, fairly well put-together. You try to make sure your shoes are from the same pair.”

She then informed us that she’d be wearing a business suit for her photo shoot. “I’m not wearing an evening gown; it’s the wrong image.” The scads of evening gown photos are not how she views herself, or at the very least, not how she wishes to present herself. “There are enough pictures like that, so I’ll just wear a simple business suit.

Diana Taylor was born in 1955 in the upscale Connecticut suburb of Greenwich, Connecticut, the daughter of a schoolteacher and a biochemist for Union Carbide chemical company.

She went to college at Dartmouth and was in the second class of women to go all the way through all four years. “There were two hundred of us, or maybe three hundred of us,” she said “And three thousand of them at the time.” Not entirely a bad ratio in certain respects, she admitted. “It was so much fun. I had a blast; I loved it. And my best friends to this day are people I met my first week at Dartmouth.” (Ms. Taylor is now a member of her alma mater’s board of trustees.

Much of what happened after Dartmouth was a matter of serendipity. “I have basically fallen into everything I’ve ever done,” she said. “I’ve never really planned anything. I’ve basically seen opportunities as they come up and they’ve turned out to be really good ones.

But there was one thing she planned: “I knew was that I wanted to move to New York City [after college]” she said. Like many twenty-somethings who decamp to Manhattan after undergrad, Mr. Taylor’s roommate from Dartmouth was living in a one-bedroom apartment with one other roommate and they were looking for a third.  But Ms. Taylor needed to find a job. She was interested in health care and began sending resumes to hospitals but “unfortunately none of them wanted me as their hospital administrator at that point.” She got a job in government in the department of social services but realized quickly that it wasn’t where she wanted to end up, so she applied to business school in a joint degree program that also included a public health degree.

But she was still working on top of that. “I was an evening and weekend administrator at St. Vincent’s hospital in Brooklyn, which was an experience,” she said. “It was fascinating.” She was also working at Smith Barney in their public finance department and received an offer for a full-time job when she graduated. She moved on to Lehmann Brothers with a couple of her colleagues from Smith Barney, and then on to Donaldson Lufkin & Jenrette.  And then a couple of guys from Lehman went to DLJ and they took me with them. “And then some guy I didn’t even know at the time called me up [four years later],” she explained, “And said ‘I’m starting this new firm do you want to come join?’ And I’d basically hit the ceiling, if you will, at DLJ and it sounded like a good idea, so I did that. Stuff happens at really good times!”

In 1996, she made a transition to public work as Assistant Secretary to then governor, George Pataki. After brief stints at Keyspan Energy and the Long Island Power Authority (where she served as CFO) she returned to Governor Pataki’s office as Deputy Secretary and became Superintendent of Banks in 2003.

In 2007, she returned to the private sector as a managing director at Wolfensohn Fund Management, but still hasn’t fully extricated herself from public life.

And how could she?  She’s partner to the most powerful man in New York City politics. Which has its particular downsides. “Oh it’s hilarious,” she laughed. “I have the scars to prove how many times I’ve been knocked over the head by TV cameras running to get a picture of the mayor.” But, she notes, it’s also not without its pleasures. “Actually I love observing life,” she explains. “And it’s a great place to observe from. You see a lot in this kind of position and it’s incredibly rewarding.”

That said, the reality is that when Ms. Taylor walks into a room with the Mayor, she’s not recognized as Diana Taylor, managing director at Wolfensohn, or Diana Taylor, former Deputy Secretary to the governor. She’s Diana Taylor, girlfriend of Michael Bloomberg.  For a woman with her own impressive resume and laundry list of accomplishments, it must be a little, well… ego-bruising.

But Ms. Taylor insisted it was just part of the role she had chosen to play. “One of the things that you just need to remember is that it’s not about you,” she said. “He’s the elected official and you’re there for support. And if people want you to do something, you do it and if they don’t, you don’t.  He’s the one who was elected and I wasn’t.”

But, she acknowledged, “That’s one reason why it’s really good that I’m busy. He’s doing his thing and I have my life, too, and things that are important to me.”

And many things are important to Ms. Taylor these days. She’s on the board of ACCION International, a microfinancing organization that provides loans to small businesses that are under-serviced by banks in emerging economies and recently visited Brazil and Honduras on behalf of the organization. In June she was named to the board of the YMCA of Greater New York. She’s a director of Sotheby’s, Citigroup and Brookfield Properties.

She’s also involved in a variety of charities that benefit women and girls. And she’s a natural advocate, having been one of the few women in a variety of traditionally male-dominated environments.

“I think one of the problem that most women have is that they’re not really good at advocating for themselves,” she said. “They’re great at advocating for other people.  They’re hard workers, they’re really smart but they’re not very good about marching into their boss’s offices and saying ‘I need a raise! So-and-so got a raise and I work better and harder than they do and am more productive than they are. Women are just not particularly good at that.” It was a broad generalization, she said, but “women tend to have the attitude that, ‘if I put my head down, I work really hard, I’ll get recognized’. And life is not fair. That’s a hard thing.”

She attributed much of the gender lopsided-ness to natural attrition rates as women dropped out of the work force in order to have children. “A lot of time you find it’s a decision they make to have a family. And they’re bringing up kids and working and something’s gotta give, and the work’s not rewarding enough and they’re not getting enough back from their work situation, so they say, you know what? I can’t.”

Her own decisions were made years ago—what she described as organizing a series of priorities. And for better or worse, being childless probably helped her career. “I’m sure it did,” she said. “I never had to run home and help anybody with their homework. That was a whole very time-consuming aspect I didn’t have to worry about. “

But, she adds, “you have to do what you’re comfortable with and what makes you happy and that’s not the same for everybody.”

And in looking at Ms. Taylor’s choices, the ones paths she decided not to take are as significant as the ones she did.  Last year, Senate Republicans approached Ms. Taylor about the possibility of running against incumbent Senator Kirsten Gillibrand, and for a while she considered it. “The Senate Republicans basically asked me to run and I thought about it, talked to a lot of people,” she said. “But then when I really thought about it, what attracted me to the idea was the race because I knew I could win that race. It was the thought of actually having to go and do that job, that was really not all that appealing.”

When asked what she thought of Senator Gillibrand’s job performance now, she paused. “I think she works very hard” she said, diplomatically. “I don’t agree with her on anything—“ She hesitated. “Some things that…” Then choosing the if-you-can’t-say-something-nice option, she reiterated: “I think she just works really hard.”

But Ms. Taylor insisted she wasn’t tempted to run against her now either. She said she had no political ambitions. “I never did!”

She also brought up a complicating factor in any Senate—the convoluted and often antagonistic relationship between the city and the state. “Because what’s good for the state of New York and what’s good for the city of New York are not always aligned and I’d be representing the state.

“Plus, I’d have to go live in Washington?” she said, rolling her eyes. “And you know, what would I do with the dogs? Would I take them on the train? Would I have to drive? These are the kinds of considerations!”

Then she turned serious. “You’re one of a body of 100. I would be a very junior member of the minority party and I didn’t feel like I’d have a lot of say in what went on and the decisions that were made. And I don’t have a particularly high opinion of Congress at this point.”

We pointed out that no one had a particularly high opinion of Congress at this point. (A recent Gallup poll indicated that Congress’s approval rate had dropped to a measly 13%.)

“Then I hold the majority opinion on that, l and I think that we’re in a situation now where it’s sort of a downward spiral,” she said. “You know, the opinion of the body itself is so bad, how do you get qualified intelligent good people to run? I don’t know the answer to that question.”

Everyone has a theory about why things are bad when they are–and as a corollary, how they got that way. Ms. Taylor thinks the system itself can’t work in its current incarnation. And not just some piece of the system; the entirety of democracy.

“I put this in the context of [the notion that] democracy is the worst system except for all the others. I don’t know what you replace it with and how you fix this. But it does sort of go to the lowest common denominator.”

And the primary system is one of the culprits, according to Ms. Taylor. Take the districts in the House of Representatives, for example.  “Most of them are completely gerrymandered to be safe districts for whatever party’s in control. And when you have something like that with the primary system, you have people [winning] the primary in the majority party of that district.”

“There are not very many people who go out and vote in primaries,” she added. “So to get elected in a particular district, you have to appeal to the five people who vote in the primary. So you get elected, and you get into office and you have zero incentive to do anything that does not fit with [the agenda of] those five people who elected you, who are the wacko right-wing or the wacko-left wing depending on what kind of district you’re coming from—so you have no ability really to go to the center because you will not get re-elected if you go the center.”

Re-election incentives have always been a big part of New York City political discourse. Especially with regard Ms. Taylor’s boyfriend, whose three-term mayorship has been the source of much controversy over the years.

But she’s changed her mind on that one.  “I used to be completely for term limits,” she said. “I thought it was a great thing. But basically what happens with term limits is that the staff takes on huge power because they’re the ones who have the institutional power. I’m not sure that term limits is a particularly good thing.”

The key, she said, was changing how districting worked. “I think that non-partisan primaries would be great. I think that would make a lot more sense. Because then you have the whole slate and you don’t have people who’ve run on the total right and total left having to have one set of ideas during the primary and then move to the center for the re-election.”

Along those lines, the current field of Republican presidential candidates didn’t seem too promising. A ripple of irritation passed her expression. “I don’t really like any of them very much. A lot of them scare me… a lot.”

“I’ve never met [Michele Bachmann]. I have read a lot about her and I’m not particularly impressed by what I’ve read.”

As for the other Republican beauty queen-cum-politico: “I have met [Sarah Palin] once, just very briefly. If I were her, the best thing she could do is keep the buzz going and then not run. And she’s doing just fine doing that.”

She was even less sanguine about Obama. “I think that he’s a very intelligent man,” she said carefully. “And he has a lot to learn.”

Her voice took on a sharper edge. “For somebody’s who’s going to come in and be the great unifier—you know, that hopey-changey stuff—it hasn’t worked very well. The country is more divided now than it’s ever been. And he doesn’t appreciate other people and what they do. “

Having given this some thought, she had a three-pronged list of his biggest mistakes. “There are probably more,” she said, but here were three.  He wasn’t supporting business, Ms. Taylor said. “He should be a champion for this country and he’s not. Because that’s where the jobs are going to come from. They’re not going to come from government; they’re going to come from the private sector.” The second: Obamacare. He basically told Congress, ‘you know what? I want a health care bill, do something.”

“The last time I checked, the president was supposed to sit down and figure out what he wanted and then get Congress to go along with it. And we got a mess. And exactly the same thing with financial regulation and regulatory reform.” This was number three. “And we have a mess.”

And Ms. Taylor would know a bit about the banks, having worked in both the public and private arenas of banking for decades. Economic uncertainty was making it difficult to get anything done, she maintained. “I mean, Dodd Frank has like 400 things that need to be done—you know, changes, and the regulators have to go and promulgate rules and regulations around those things—and they can’t do it. There’s so much uncertainty. And whoever has created a situation now where they’re basically saying to the banks, well, we want you to lend money, but you can’t lend money to anybody who actually needs it!”

Here she became more animated. This was far more interesting to her than Ralph Lauren dresses. “And this whole business of the FHFA suing all the banks around Fannie and Freddie; it’s crazy!” Inasmuch as Mr. Taylor would ever be inclined to pound her fist on a table to make a point, she seemed on the verge of it. “I’ve never—I mean, it just makes no sense at all to me!”

And then there was a glimmer of what Diana Taylor, Freshman Senator might be like. “I think it’s a problem throughout the system,” she said, gearing up her delivery. “I think it’s a problem with Congress. I think it’s a problem with the ratings agencies. I think it’s a problem with the banks. I think it’s a problem with the population at large.  Everybody’s going like this” she threw her hands up in the air. “And at the end of the day, everybody’s responsible in some way or another.”

As for what Ms. Taylor is responsible for, she still wants to tackle public health. She’s on the board of the Mailman School at Columbia and said her studies there had informed her thinking on things like microfinance “and what people actually need to survive and make their lives better.”

It’s still easy to imagine her getting involved in some tangential way, though—maybe even with her former boss, ex-governor George Pataki, who’s reportedly mulling a presidential campaign.

“Yeah, I don’t think that he’s going to run,” she said. “He’s an absolutely great guy, and if he decides to do it, I wish him the best. But I think there’s a pretty large field right now.” And there was the primary problem again. “You’re never going to get through a republican primary if you’re pro-gun control, pro-choice. He is a lot more liberal than run of the mill”.

Ms. Taylor self-identifies as a Republican, but is socially liberal herself, though fiscally conservative—a libertarian lite, perhaps.  “I’m socially very liberal. I don’t understand why anybody cares who marries who. I think that guns should not be in the hands of criminals, and I’m rabidly-pro-choice. It’s nobody else’s business, and I’m fiscally quite conservative.” She says she may have inherited this from her family. “My mother has a bumper sticker on the back of her car that says ‘pro-family, pro-child, pro-choice.’”

So we were curious: where might she clash with the Mayor, whose politics occasionally differed. She shook her head, determinedly: “Not going there!”

editorial@observer.com

This story appeared in the October issue of NYO Magazine.

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