Bill de Blasio. Image by Getty Images

New York City Mayor Bill de Blasio’s 2015 trip to Israel was not as bulletproof as he first thought.

De Blasio, under fire at the time from local news outlets, first broached the subject of a visit to the Jewish state as part of a summer 2015 family excursion that included speaking at the Vatican, telling several aides he would “defy any purveyor of conventional wisdom to beat a Vatican – Holy Land trip for bulletproofness!” according to a trove of internal emails released on May 24 as part of a public records request.

De Blasio first emailed his advisors after receiving an invitation to speak at an event attended by Pope Francis.

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“So the current thinking is to compress all our overseas travel into a week or so, anchored by this Vatican event,” the mayor messaged aides on May 25, 2015. “So that would mean one trip including Israel and the Vatican — I wonder if the tabloids would be able to criticize THAT :)”

The mayor did not end up traveling to Israel until that October. That trip took place during an outbreak of violence, causing him to cancel a planned meeting with Palestinians in the West Bank and later say he did not “want to pretend to understand the nuances of the situation.”

Israeli businessman Baruch Eliezer Gross paid at least $25,000 to fund the trip, which was cleared by the city’s Conflicts of Interest Board, but still became fodder for the very tabloids he said would not be able to find a way to criticize him.

The mayor’s office did not respond to an immediate request for comment.

Contact Ben Fractenberg at [email protected] or on Twitter, @fractenberg

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