Conway met Trump in 2006, when she served on the condominium board at Trump World Tower in Manhattan. She said Trump seemed surprisingly hands-on, showing up at meetings to hear the residents’ concerns. She thought then he was much kinder than his public persona suggested.

He called her over the years, following a familiar prompt: I saw you on Hannity. I saw you on CNN. What do you think of this?

In March 2015, Conway said, they met to discuss his presidential bid. She declined to work for him, thinking: I’m not sure if this guy would ever care about polling. She worried about how the public would perceive their partnership. “Like, ‘What are you doing there?’ ” she said. “Riding on a plane? Whispering in his ear about what he should say to women?”