Joel Klein, the former leader of the New York City school system, met repeatedly with Jeffrey Epstein in 2013, years after Mr. Epstein was convicted of soliciting prostitution from a minor.
At the time, Mr. Klein had left government and was working in education technology. He said the meetings came about at the request of his friend Mortimer Zuckerman, the media and real estate mogul. Mr. Zuckerman had been considering hiring Mr. Epstein for estate planning, and had asked for Mr. Klein’s advice on the matter, according to Mr. Klein.
Mr. Klein ultimately advised Mr. Zuckerman against the hire, Mr. Klein said in an email to The New York Times. The Zuckerman family declined to answer questions on the record.
Still, according to Mr. Epstein’s emails and other documents released by the Justice Department, Mr. Epstein and Mr. Klein appear to have discussed issues beyond estate planning, including their shared interest in education. Mr. Klein was leading Amplify, at the time a struggling education technology outfit then owned by News Corp. It has since grown into a respected purveyor of curriculum materials in science, reading and other subjects.
For years, Mr. Epstein cultivated a network of high-powered contacts in finance, media, academia, entertainment and technology. But the emails with Mr. Klein and others show he also got involved in K-12 education, during a time he was attempting to bolster his reputation through philanthropy. Mr. Epstein announced investments in charter schools and other education efforts serving low-income children, including a network of high schools affiliated with Bard College.
He frequently exchanged emails about learning and brain science with academics, and was curious about the potential of video games and other technologies to improve student outcomes.
In preparation for one meeting with Mr. Klein, he wrote to a contact in the tech world, “Im meeting with Joel Klein on monday, any edutainment games that you like already out there.”
Mr. Epstein was also attracted to the idea of charter schools, independent public schools that are generally not unionized. In 2012, his foundation announced a donation to the Maya Angelou charter schools in Washington, D.C., which were known for serving low-income children with serious behavioral and academic challenges.
The Angelou schools did not immediately respond Friday to a request for comment.
According to the Epstein documents, Mr. Klein met with Mr. Epstein at least six times in 2013 — at a dinner party in Mr. Epstein’s Manhattan home alongside Mr. Zuckerman and others, and then for breakfast and afternoon meetings.
Mr. Klein did not answer questions about what he knew of Mr. Epstein’s criminal record during the period in which they were in frequent contact. “I never met Epstein anywhere other than at his house in New York, and I had no further contact with him after late 2013,” he said.
Mr. Epstein connected Mr. Klein with Joichi Ito, a prominent venture capitalist and technology expert.
Mr. Klein then wrote in an email to Mr. Ito: “would love to talk to you about what we’re doing at Amplify.”
Mr. Epstein also wrote emails referring to his desire to introduce Mr. Klein to Ehud Barak, the former Israeli prime minister who became a tech investor.
Mr. Klein said he never met with Mr. Barak. He said he met with Mr. Ito because he was a “distinguished technologist.” Mr. Ito would eventually resign from M.I.T. and the board of The New York Times Company because of his Epstein ties.
Mr. Barak and Mr. Ito did not immediately respond to requests for comment.
In a written statement, Amplify, which is now an independent company, said it had not known Mr. Klein had met with Mr. Epstein. A spokeswoman, Kristine Frech, said Mr. Klein left the company in 2015, when it was sold to a group of investors led by the Emerson Collective, the organization founded by Laurene Powell Jobs, Steve Jobs’ widow. Ms. Frech said neither Mr. Epstein nor any of the contacts he provided to Mr. Klein had played a role in Amplify, including as investors.
Before his career in education, Mr. Klein led the Justice Department’s antitrust division under President Bill Clinton. He was appointed schools chancellor by Mayor Michael R. Bloomberg in 2002, and quickly became a leader in the national movement for school choice and accountability.
After stepping down from his public role in 2010, he joined News Corp., whose Amplify education division attempted to sell tablets to schools pre-loaded with curriculum materials and educational games. That effort failed; the tablets were glitchy, and school systems eventually preferred to purchase simple laptops.
In one exchange between Mr. Epstein and Mr. Klein in 2013, the financier invited Mr. Klein and his wife to a birthday party he was planning for Woody Allen. Mr. Epstein asked Mr. Klein for advice on other guests to include, preferably people who were “not ponderous.”
Mr. Klein responded, “Most people are ponderous, I fear.”
Mr. Klein said he did not end up attending that particular dinner. Mr. Epstein’s emails are filled with guest lists for dinner parties that may not have taken place exactly as planned.
Georgia Gee and Kirsten Noyes contributed research
Dana Goldstein covers education and families for The Times.
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