As Mayor Michael Bloomberg's choice for Schools Chancellor, Cathie Black, came under attack in late 2010, City Hall engaged in a breathless push to rally celebrities, including Oprah Winfrey, to support the embattled nominee.
The mayor's former chief of staff, Stu Loeser, wrote a victorious email after Winfrey eventually did speak to the Daily 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!”
The details surfaced after the Bloomberg administration was forced by the state's highest court to release a series of email exchanges that have been requested by a Village Voice intern under New York's Freedom of Information Law. Black's nomination was ultimately approved by the state education commissioner but she was forced out fewer than 100 days later, in April of 2011, as the negative publicity surrounding her appointment continued to swirl.
The emails between Black and various City Hall officials show how Black grew anxious when attempts to secure endorsements from Congresswoman Carolyn Maloney and Caroline Kennedy fell through.
"Is our strategy working?" Black asked then-deputy mayor Dennis Walcott and legislative aide Micah Lasher, after reading a New York Times story about her nomination on the morning of Nov. 16. "Do we have to take another course? Or hold steady?"
One email listed a spreadsheet of elected officials, plus an aide to U.S. Education Secretary Arne Duncan and former New York City teachers union president Randi Weingarten, with notes stating whether or not these individuals would be helpful.
"All our focus needs to be on getting allies to come out in support and on getting you prepared for a tip you as soon as possible," Lasher said. "We will make a few more base-covering calls, but clearly the political community will do what they will do. We will be fine."
At one point, Black suggested an endorsement from Ivanka Trump but City Hall declined to pursue it. She did win an endorsement from Gloria Steinem.
The emails were released on Thursday after City Hall lost its last attempt to keep them from going public. Two lower-level courts had ruled against the city, and the state's highest court declined to hear an appeal.
The original request to release the emails came from Sergio Hernandez, who was an intern at the Village Voice in late 2010. When the city declined his request, he was represented by a legal clinic at Yale University and then by a Manhattan law firm working pro bono.
Hernandez, who is now a business editor at The Week, said he also filed Freedom of Information requests to figure out how much money the city spent fighting the case. He said the total was $25,000 as of the end of 2012 and he is seeking to find out how much the city has spent since then.
"I'm actually more surprised that they spent so much time and effort trying to prevent the release than by anything that's actually in the emails," he said.
"It's interesting to me that not one of the people they reached out to have much to do with education or schools or anything that really would have lended credence to Cathie Black's qualifications for the job," he added. "It's an interesting sort of window into the mayor and his offices thinking during this sort of fiasco."
He also noted that there was not one direct exchange between Bloomberg and Black. See the emails below.