Michael Appleton for The New York Times
Cathleen P. Black, the mayor’s pick to lead New York schools, waiting for a taxi outside her Park Avenue apartment.
By DAVID M. HALBFINGER, MICHAEL BARBARO and FERNANDA SANTOS
Published: November 18, 2010
She grew up sheltered and privileged, in a middle-class Irish enclave of Chicago at midcentury, attending Catholic schools and riding horses at a country club where blacks and Jews were not allowed. Yet from age 28, she blazed a trail for working women, persuading male-dominated Madison Avenue to get behind an upstart magazine called Ms.
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Ms. Black and her husband, Thomas E. Harvey, at a media and technology conference in Sun Valley, Idaho, in July.
She was the newspaper industry’s chief lobbyist in the 1990s, fighting a ban on tobacco advertising, and she occasionally mused about running for office. But she has otherwise barely dabbled in the public sphere: describing her strengths in internal documents, the Coca-Cola Company, where she is a longtime board member, leaves unchecked the box next to “governmental, political or diplomatic expertise.”
She has shown a common touch as president of Hearst Magazines since 1995 by riding in yellow cabs rather than black limousines. At the same time, she is given to showy extravagance, lending a $47,600 bracelet — a Bulgari confection called the Allegra — to a Manhattan museum for its current exhibit showcasing the jewels and clothing of New York’s most influential women.
Cathleen Prunty Black, who is Mayor Michael R. Bloomberg’s choice to be the next chancellor of the New York City public school system, has during more than 40 years in the publishing industry broken numerous glass ceilings — and amassed a personal fortune — with quick and definitive decision making, crystal-clear goal setting and an all-surpassing attention to the bottom line. She not only produced results but also carefully managed up, winning the confidence of powerful bosses like Allen H. Neuharth and Rupert Murdoch. And she threw herself into knotty problems, developing two tennis elbows from carrying around overstuffed briefcases in her first year as president of USA Today.
“She’s the closest thing to Superman that exists,” said Atoosa Rubenstein, on whom Ms. Black placed an audacious bet, letting her start a new magazine, CosmoGirl, at age 26.
But while Ms. Black, 66, has been a highly visible and celebrated corporate executive, she has rarely spoken out on the big issues of the day. Her civic engagement and philanthropic activity are scant beyond donating money to politicians and charities and inviting political figures like Mr. Bloomberg, former President Bill Clinton and Cindy McCain to speak at Hearst functions.
There is also little evidence that Ms. Black has until now had to wrestle with the challenges of the school system, including race, poverty, immigration and public health, never mind pedagogical and philosophical questions like teacher tenure, charter schools or the new math.
“It will certainly be a challenge,” said her sister, Susan Webb, 74, a decorator who lives outside Chicago. “But my sister loves a challenge.”
If the state education commissioner grants Ms. Black a waiver from the law requiring leaders of school districts to have substantial education credentials and experience, she would take over a system whose size, demographics and challenges are like nothing else she has tried to manage.
Its one million students — two-thirds of them poor enough to qualify for free lunch; 85 percent of them black, Hispanic or Asian — bear little resemblance to the middle-class, middle American consumers she has spent her career appealing to.
Its more than 80,000 unionized teachers and principals cannot be easily fired if they fail to meet expectations, the way she replaced editors and publishers who did not make their numbers.
And many of its 1,600 schools have challenges far beyond that of any printed product or company whose brand Ms. Black has tried to “refresh and reinvent,” to use one of her catchphrases.
Ms. Black, a mother of two, has refused interviews since her appointment. But conversations with dozens of people who know her — her siblings, lifelong friends, famous neighbors, bosses, employees and competitors — show that in a life of daring leaps and many firsts, Ms. Black’s aspiration to lead the nation’s largest school system is far and away her riskiest move.
One subordinate likened the news to a bulletin that Ms. Black had decided to “move to the North Pole and become Santa Claus.” But others see it as a fitting capstone and have no doubt her sheer devotion and force of personality will propel her to success.
“Cathie is kind of a Bill Clinton character: if you’re with her and if you’re in conversation with her, nothing else matters,” said Jane Dammen McAuliffe, a college classmate who is now president of Bryn Mawr College. “She always found a way to galvanize people around some ambitious agenda.”
Eager to Stand Out
At 12, she changed the spelling of her name to Cathie, to stand out. It was a childhood she says was idyllic, growing up on the South Side of Chicago near the South Shore Country Club, where she played tennis and won ribbons in dressage, the equestrian sport.
Each week, Ms. Black’s mother took the three children to Mass at St. Philip Neri, a large stone church with a turquoise steeple. Her father, James, ran a food company.
“You kind of knew, very definitely, that we had some advantages,” said her brother, Jim, 70, a retired manufacturing executive who lives in the Chicago suburbs.
At the all-white, all-girls Aquinas Dominican High School, Ms. Black was a hard worker but not a straight-A student. In 1962, she followed her sister to Trinity College in Washington, where Ms. Black tutored children at a local public school and at an orphanage.
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A photo of Ms. Black in the 1963 yearbook from what was then Trinity College in Washington, D.C.
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Ms. Black lent a $47,600 bracelet to a museum exhibit showcasing the clothes and jewelry of influential New York women.
The next year, she was among the legions who waited for hours outside the Capitol for a chance to walk past President John F. Kennedy’s coffin. Classmates recalled Ms. Black as a sort of Pied Piper who organized trips to Garfinckel’s, a downtown department store, and to mixers at Georgetown.
An English major, Ms. Black spent a year studying in Rome and traveling across Europe, celebrating the New Year in Egypt, fleeing an uprising in Syria and hitchhiking to Northern Ireland to see relatives. The adventure, she has said, made her think “this is a very big world and I want a big bite out of it.”
So she headed to Manhattan, sharing an apartment on East 80th Street with three classmates, and earning $85 a week selling advertisements for Holiday, a travel magazine. “Our goal wasn’t to leave college, get a husband and be model housewives,” a roommate, Kathleen M. Doyle, said. “We wanted to have our careers, and we worked really hard.”
She had been on the job for a year when her boss quit. Not entirely qualified, Ms. Black nonetheless asked for the job — and then demanded to match her predecessor’s salary (she got the title but not the money). She went from there to the nascent New York magazine, and then to Ms., where Ms. Black instantly saw opportunity she could not seize in the martini-fueled, heavily male publishing world.
“She understood that she was not going to get the kind of shots that the guys who had just graduated from Georgetown were getting,” said Patricia Carbine, the publisher who recruited her as the advertising manager of Ms. in 1972. “She had zero to lose and God knew what to gain.”
The trick was getting advertisers to take female consumers more seriously and buy space in a publication that was being derided, as Ms. Carbine put it, as “a lesbian magazine for women who don’t shave their legs, who aren’t normal.” Ms. Black’s tailored suits stood out amid the editors’ blue jeans and wild hair. “When advertisers looked at her, they thought, ‘Maybe these people are not as bad as they seem,’ ” recalled Gloria Steinem, a founding editor. In sales meetings, Ms. Black would insist that Ms. Steinem and her co-founder, Letty Cotton Pogrebin, stay focused on closing the deal.
“She said, ‘There are all kinds of feminists — I’m one, Gloria’s one, we have feminists who are homemakers,’ ” Ms. Pogrebin recalled. “ ‘If you want to reach them all, they’re reading us — you’d better get on this bandwagon.’ ”
But the style that succeeded with advertisers caused problems internally. Early in her tenure as ad director, Ms. Black’s staff mutinied, threatening to quit en masse because of her harsh management. “I told her that it was important to be both empathetic and sympathetic as well as firm and strong,” Ms. Carbine said.
Her pragmatism, too, sometimes clashed with the magazine’s mission. When Ms. Steinem and others wanted to make a stand by rejecting advertisements from Virginia Slims, whose new slogan, “You’ve come a long way, baby,” they found offensive, Ms. Black insisted on accepting a small ad, which incensed readers. She backed down, but in her 2007 memoir she griped that the decision cost the magazine “untold millions.”
Ms. Black’s best-selling book, “Basic Black,” is a readable, anecdote-laden, how-to guide — not so much about the business of business, as about how to operate in the corridors of power. There are handy tips — wear Burberry when meeting someone from Burberry; greet guests at the door of an office party and depart before they get tipsy — sandwiched between recountings of triumphs large and small.
For example, when she discovered that House Beautiful had misidentified the owner of an Aspen retreat as Ronald Lauder, the cosmetics magnate, when it really belonged to his brother, Leonard, Ms. Black tracked Leonard down in Paris to apologize. “This was a micromanagement issue that was really of no consequence,” his wife, Evelyn, said this week. “I was extremely impressed.”
She mastered the art of the touching personal gesture. After Mr. Neuharth, the founder of USA Today, tried to woo her by sending a limousine with a basket of treats to her Connecticut home, Ms. Black responded by presenting him with a giant homegrown tomato over lunch at the Four Seasons. She took the job as president of the newspaper, and later commandeered the Gannett Company jet to fly executives to the funeral of a top deputy’s father.
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But even as she institutionalized flexible work schedules, established an internship program and mentored people like Ms. Rubenstein at Hearst, Ms. Black also battled criticism that her day-to-day management style was unfeeling and intimidating, particularly to younger women. Executives quickly learned never to go into a meeting unprepared or to beat around the bush. “There’s no dillydallying,” said Gayle King, editor at large of O: The Oprah Magazine. “She has an agenda and that is it.”
Ms. Black was not afraid to call people out in front of large groups. “ ‘What are you saying’; ‘you’re not being clear,’ ” Ms. Rubenstein recalled hearing her say more than once. Another former editor, who like others insisted on anonymity for fear of offending such a powerful industry figure, remembered being snapped at: “You’ve been talking for five minutes, and I still don’t know what you want.”
And many people say they felt that she was judging more than their work. “You feel she is making very strong, intuitive decisions about you with every word you speak,” said another woman who worked under her.
“Nice shoes,” Ms. Black told one woman who showed up for a second job interview, before adding, “You wore them the last time.”
Throughout her career, Ms. Black has displayed a gift for wiping away red ink: making New York magazine profitable, attracting skeptical advertisers to USA Today and, at Hearst, inventing several winning titles during an era of industry decline. She sold Oprah Winfrey on the idea of the magazine, which became Hearst’s most successful new one ever; in 2008, her new Food Network Magazine exceeded one million circulation. Ms. Black also saw hard times coming years before Hearst’s rivals did, and began making layoffs, closing troubled titles like Tina Brown’s Talk and streamlining production soon after 9/11 and the burst of the dot-com bubble.
“That prepared us,” David Granger, the editor of Esquire, said. “And she didn’t let up.”
But the most vexing riddle facing print media also confounded Ms. Black. Hearst spent tens of millions of dollars trying to figure out how best to exploit the Internet, and made what some executives saw as rash decisions, first in being a partner with the Web start-up iVillage, then by creating its own costly digital division.
Throughout, colleagues said, she was eager to help executives sort through difficult issues — within limits.
“At various points, she’d lay it out for me,” Mr. Granger said. “ ‘Things are not going well; unless things change, I’m going to have to make a change.’ ”
Ms. Black has said she hates the expression “having it all,” preferring to speak of “achieving balance” between life and work. But while it may look as if she does have it all — beautiful homes, two children and a black Labrador named Madison, a soaring career and the right outfit for every occasion — achieving that balance was a struggle.
Her first marriage, after a 1970 wedding at the Church of St. Thomas More and a reception at the Plaza Hotel, ended in 1976. “We were focused too much on our jobs,” said James O’Callaghan, a stockbroker.
Six years later, Ms. Black married Thomas E. Harvey, a lawyer and Vietnam veteran, in her Upper East Side apartment. They moved to Washington, where Mr. Harvey worked for the Senate and Ms. Black, after USA Today, led the American Newspaper Publishers Association.
At that trade group, her biggest achievement was setting up a national network to sell advertisements in local newspapers; it generated $30 million. She also eliminated scores of jobs, and she paid herself more than double what her predecessor made — in her first year, $1 million — prompting some publishers to quit.
In 1987, she and Mr. Harvey adopted a son, Duffy; she returned to work four weeks later. The baby shower for her daughter, Alison, adopted in 1991, was hosted by Marilyn Quayle, wife of the vice president. The next winter, recalled John Sturm, the association’s general counsel, whenever he spent Sundays at the office, “often the only other car in the parking lot was Cathie Black’s.”
Her return to New York was in grand style: in 1996 she and her husband bought a Park Avenue penthouse duplex with a vast kitchen, where she has lived above Lloyd Blankfein, the Goldman Sachs chairman, Stanley O’Neal of Merrill Lynch and Tom Brokaw of NBC, who says he sees her most mornings before dawn working out with a personal trainer in the basement gym. “I get the impression that there are not idle moments in her life,” Mr. Brokaw said.
In 1998, the Harveys bought a white clapboard house with a pool in Bridgewater, Conn., for $1.15 million. (It was recently reported sold; the asking price was $2.35 million.) In 2006, they added a $4.1 million home in Southampton. Ms. Black has earned at least $4.7 million in cash and stock over two decades from serving on the boards of Coke, I.B.M. and iVillage, according to Equilar, a company that tracks corporate compensation, and her current stock holdings in those companies are valued at about $8 million.
Her parties are legendary: a 50th birthday bash under a tent in her Washington backyard attended by the Quayles; her 60th at a rented villa in Tuscany, with 75 relatives and friends; and the annual pre-Thanksgiving fete that brings 100 or more of Manhattan’s boldfaced names to the penthouse.
Ms. Black belongs to the New York Athletic Club and to a Westchester County golf club where the initiation fee today is about $300,000. She is a trustee of the Kent School in Connecticut, where her children graduated, and of the University of Notre Dame, which her son left after a semester. (He plans to enroll soon in a community college.)
Out of Reach
The only brass ring left — a coveted seat on the board of the Hearst family trust — has eluded Ms. Black’s grasp. And this summer, a rival from Condé Nast was handed her job, while she was given the title of chairman but with diminished responsibilities.
Then the mayor called. Ms. Black was as surprised as everyone else.
She had rarely before weighed in on current events, apart from holding a corporate retreat in New Orleans after Hurricane Katrina, or reassuring workers the day after 9/11 that the best thing they could do was to continue working.
Yet Ms. Black is fulfilling some people’s expectations. When Ms. Black moved to Washington, many thought she had a career in politics in mind, said Wenda Harris Millard, who has known her for decades. At the newspaper association, some suspected she wanted to run for the Senate. Now, there is already chatter in her circle that schools chancellor may not be enough.
In three years, they wonder, will Ms. Black run for Mr. Bloomberg’s job?
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Reporting was contributed by Jack Begg, David Carr, Alain Delaquérière, John Eligon, Emma Graves Fitzsimmons, Trip Gabriel, Elissa Gootman, Christine Haughney, Sarah Maslin Nir, Richard Pérez-Peña and Jeremy W. Peters.
A version of this article appeared in print on November 19, 2010, on page A1 of the New York edition.
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