Ms. Makler began looking for a new job in New York. She said she heard nothing from Mr. Cailan until September. “Yo! Are you officially in NYC?” he texted. She responded, reminded him of the details of the encounter and wrote: “This all boils down to how I no longer think it wise to work for you, let alone look you in the eye.”

He responded apologetically. “I did not intend to take advantage, but understand that I used poor judgment,” he said. “I hope you can forgive me. You are a rockstar of a professional and you are going to be great.”

Mr. Cailan’s star continued to rise. He was named a brand ambassador for Bordeaux wines; the Usual landed on Wine Enthusiast magazine’s list of “America’s 100 Best Wine Restaurants 2019,” and he made it a destination for winemakers’ dinners and “industry nights,” after-hours gatherings for restaurant workers, where professional connections are made and wine flows freely.

That is how Ms. Fernandez met him. She was on the bottom rung of the wine world, having moved from an academic career in public health. She said Mr. Cailan seemed supportive and capable of treating women with professional respect.

Around 1 a.m. on June 14, Ms. Fernandez received a text message from Mr. Cailan. She had been trying to get him to taste some wines she was representing, so she agreed to meet him in the bar at Atoboy, a restaurant near where she works.

“As soon as I got there, I could see he had no interest in the wines,” Ms. Fernandez said, noting that he appeared intoxicated. They talked shop, until he suddenly leaned over and kissed her on the lips.

When they left the bar, Ms. Fernandez was mildly intoxicated, and when Mr. Cailan invited her to his apartment to taste more wines and watch television, she agreed. There, she said, he started kissing her aggressively and trying to slide his hands under her dress. Ms. Fernandez immediately pulled back. “That’s not going to happen tonight,” she said she told him.