Cathie Black Woos Oprah in E-Mails the Bloomberg Administration Didn’t Want Us to See

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Cathie Black.Photo: Michael Loccisano/Getty Images

Now we know why the Bloomberg administration spent more than $25,000 of taxpayers' money to fight the release of e-mails concerning the "Cathie Black as schools chancellor" debacle. Following a Freedom of Information Law request from Village Voice reporter Sergio Hernandez, the city refused to release the documents, arguing that making them public might "discourage public service." After losing the ensuing legal battle, the city finally released the e-mails on Thursday night, shedding light on the Bloomberg administration's efforts to combat the uproar over Black's appointment with celebrity endorsements.

Since Black was serving as the head of Hearst Magazines and had no experience in education, the Bloomberg administration needed to convince the state education commissioner to give Black a waiver to become schools chancellor. They were hoping praise from a few high-profile women could turn the situation around, and eventually Black was allowed to take the job (though Bloomberg pushed her out just five months later).

The list of celebrities to reach out to included women like Nora Ephron, Diane von Furstenberg, Suze Orman, and Whoopi Goldberg. The e-mails reveal that Black tried to make the task of publicly praising her as painless as possible, and even offered Oprah Winfrey some helpful suggestions on how she could describe her to a Daily News reporter:

Why a great schools chancellor. Tremendous leadership, excellent manager, innovator, mother of two and cares about the future of all children. Grace under pressure.

She closed, "I owe you big time." Oprah gave the interview her own spin, but borrowed a few words, declaring, "She will be a tremendous champion for the children of New York and will do it with grace."

Similarly, in an e-mail to Caroline Kennedy, Black noted that they didn't actually know each other well, but said she would "make it easy" for her to give an endorsement by just adding her name to a letter.

Aides in City Hall were enthusiastic about the effort, and thrilled when the Oprah endorsement made the cover of the Daily News. (“I was surprised to learn that we succeeded in have Oprah knock a crime story off the cover,” Bloomberg's press secretary, Stu Loeser, told the team.) However, there were limits to their groveling for celebrity supporters. When Black suggested "Would we want Ivanka Trump? Think she would do," a Bloomberg staffer shot back, "I would skip."