Screen shot 2013-05-02 at 10.51.23 PMOprah Winfrey, not education, dominated email messages between City Hall officials and Cathie Black at the start of Black’s brief and bizarre stint as city schools chancellor.

The city’s long battle to prevent the public from seeing emails about how Black, a publishing executive with no education experience, came to be chancellor for 100 tumultuous days in 2010 and 2011 came to an end today with a court order to release the messages.

The 78 pages of emails reflect communication only through 10 days after Black’s appointment in November 2010, which is when then-Village Voice reporter Sergio Hernandez filed a Freedom of Information Law request for them. Still, the emails paint a full picture of a frenzied effort to tilt public opinion in Black’s favor amid what the chancellor-nominee called “relentless press.” Those efforts centered on petitioning prominent women including Winfrey and Caroline Kennedy to endorse Black publicly.

Here’s what the emails tell us about this short, weird moment in the city’s education history:

1. Bloomberg’s choice was set a week before he publicly picked Black.  When the “small tectonic shift” of Chancellor Joel Klein’s resignation and Black’s appointment to replace him came on Nov. 9, 2010, it seemed like the news took officials at the Department of Education and City Hall by surprise, too. (Black said the job offer had come “out of left field” weeks earlier.) But at least some of them knew what was coming. Black emailed Patti Harris, the top deputy mayor, early on the morning of Nov. 3 to express concern about two other officials who had seemed poised for the chancellorship, Sharon Greenberger and Dennis Walcott, then Department of Education chief operating officer and deputy mayor for education.

“Mb very high on them,” Black wrote. “When I asked if sharon would have wanted the position both mayor, you and bob said no quite clearly. In my experience, it is rarely the case that no. 2 doesn’t want no. 1! Just better for me to know if she is crushed.” Black and Harris made plans to speak by phone. Greenberger left the department for a position at New York-Presbyterian Hospital in October 2011.

2. But three days after being picked, Black still wasn’t in email contact with Walcott or the Department of Education’s chief lawyer. She had to ask the department’s chief flak at the time, Natalie Ravitz, to connect her. And three days after that, she was still using an incorrect email address for Walcott.

Cathie Black, Mayor Bloomberg's nominee for Joel Klein's replacement, entered Tweed Courthouse for the first time today. Photo courtesy of the Department of Education.
Cathie Black, then Mayor Bloomberg’s nominee to replace Joel Klein, arrived at Tweed Courthouse for the first time on Nov. 16 amid “relentless press” about her fitness for the job. Photo courtesy of the Department of Education.

3. She also seems not to have been looped in on city affairs. Walcott sent Black a draft of Bloomberg’s budget update nine days after her appointment, and a few hours after the mayor’s press conference later that day, Walcott forwarded the city’s press release. “Not sure if I sent this to you,” he wrote. The emails are the only ones to deal with the city’s operations.

4. But she sure participated in emails about currying public favor, if somewhat haplessly. A Nov. 16 article in the New York Times about growing opposition to Bloomberg’s pick prompted a morning email from Black second guessing City Hall’s public outreach.

“Is our strategy working?” Black asked. “Based on nyt this am do we have to take another course? Or hold steady? … I am ok, honestly. Just need verification!”

Micah Lasher, then City Hall’s top legislative aide, responded with reassurance just three minutes later. “All our focus needs to be on getting allies to come out in support and on getting you prepared for a debut as soon as possible. We will make a few more base-covering calls, but clearly the political community will do what they do. We will be fine.”

In her email, Black also poked fun at a quote from UFT President Michael Mulgrew, who recommended that city needed to “manage the process so you don’t leave the candidate open for attack right from the beginning.”

“Nice quote from mulgrew. Should I call to thank?” Black wrote. Lasher does not appear to have responded to that question.

5.  The public relations strategy hinged on Oprah Winfrey. Early on, city officials seem to have decided that getting Winfrey to endorse Black was crucial to swaying public opinion in Black’s favor. On Nov. 15, Black emailed Walcott: “Did you talk to gayle about oprah?” Gayle King is the editor of O Magazine, which is published by Hearst, where Black had been an executive, and a close friend of Winfrey.

Later that day, King wrote directly to Black to let her know that her communication with Walcott had been interrupted. Black filled her in on what the city wanted: “What they hope is that oprah might issue a positive statement about cpb,” she wrote, referring to herself by her initials.

King pushed back on the idea. “But wondering who she is releasing statement to? Sounds odd to me for her to just make a comment.”

Two days later, Black reached out to King again. “All of this is coming down to the wire,” Black wrote. “What dennis hopes is to do a brief, exclusive telephone call with adam lisberg of the Daily News In which oprah would offer her support. What is the best number to get through to her?”

Shortly afterwards, an office manager at Hearst whom Black had thanked in her book wrote to Black, confused. “Please call Oprah. … She’s received emails from both you and Gayle and would like to clarify who she should call and what she should say.”

Black then wrote to Oprah, whose personal email address apparently reflects an alias she is known to use, with a script that offers a view into Black’s self-image at a time when she was taking a public beating.

“He wants to talk for five mins about cathie,” she wrote. “How you know me … why a great schools chancellor. Tremendous leadership, excellent manager, innovator, mother of two and cares about the future of all children. Grace under pressure.”

Black ended her email, “I owe you big time.”

Oprah’s endorsement came later that afternoon. Shortly afterwards, Bloomberg’s chief of staff wrote to a half a dozen City Hall and Tweed officials with the good news. “Walking past a newsstand this afternoon, I was surprised to learn that we succeeded in have [sic] Oprah knock a crime story off the cover of the News today … Surprise!”

6. Other women counted, too, although not everyone played along. While the Oprah push was still underway, Lasher put together a list of nearly 60 prominent women who might endorse Black’s chancellorship — ranging from former Public Advocate Betsy Gotbaum to Heloise, author of so many household hints —  and divvied them up for members of the mayor’s team to call. On Black’s list: Suzanne Johnson Cook, a Bronx reverend; the fashion designer Diane von Furstenberg; and Kennedy, twice.

After Black asked other members of the team, including Klein, for contact information for Kennedy, who headed the Fund for Public Schools early in Bloomberg’s term, she got a response four minutes later. She wrote to Kennedy the next morning. “We’ll make it easy” to sign the letter of support,” Black told Kennedy. But by the end of the day, Black was sounding the alarm: Kennedy had not written back.

The next day, Black had come up with another idea. “Would we want ivanka trump? think she would do,” she wrote to Lasher and Harris. Lasher’s swift reply: “I would skip.”

When the letter finally came out, six days after efforts began to recruit women to back Black, there were 28 names on the list, with prominent feminist Gloria Steinem, who had come out as an early supporter, near the top. Kennedy’s was not among them.

7. Everything Black needed to know about education policy makers fit on one page. The public relations offensive didn’t leave out the elected officials and community leaders with whom Black would have to work as chancellor. Black was given a list of at least 22 elected officials and leaders to call, most of them New York City lawmakers. The city prepped Black for the calls with a terse crib sheet.

“Audits us, not friendly to joel,” read part of the note about Comptroller John Liu.

Scott Stringer, who was then floating a run at mayor, was “trying to score political and press points off us right now on bed bugs,” read City Hall’s take. Stringer also appointed Patrick Sullivan, “who is not a team player,” to the city school board, later the site of one of Black’s biggest public missteps when she booed parents who were booing her.

8. All of the scrutiny put a crimp in Black’s social life. At 5 a.m. on Nov. 18, Black dashed off a worried thought to Harris and Debra Shriver, a top executive at Hearst. In an email with the subject line of “The party on Mon pm at Cathie’s,” Black asked, “With all of the hullabaloo, should we have security at our apartment outside on mon pm?”

The complete set of emails between Cathie Black and city officials is below.