After the meetings, Cohen would adjourn to his office at Trump Tower to plan next steps with Michael Caputo, the Republican strategist plotting Trump’s gubernatorial campaign. But Cohen surprised Caputo by talking about his own political aspirations. He told Caputo he had always wanted to run for mayor of New York City, a race he said he could win if Trump was governor.

At one point, Cohen floated the idea of a Trump-Cohen statewide ticket, an idea Caputo considered as absurd as Cohen running for mayor. “He kept bringing it up,” Caputo said. “It went from Michael Cohen interested in running for mayor to, well, ‘I’ll run for lieutenant governor under Donald Trump.’ I didn’t want to disabuse him of it, because he was our liaison. I felt like, ‘Yeah, okay Michael.’ ”