“She was a very beautiful girl with her head on her shoulders,” Mr. Zampolli said.

Mr. Zampolli said that he secured an H-1B visa for the eventual Ms. Trump, calling the process “very very easy to do.” She moved into the same Union Square apartment building where he had lived and became friends with his girlfriend, a Hungarian model named Edit Molnar.

Mr. Zampolli said the photographer of a nude photo shoot of Ms. Trump that surfaced last month on the front page of The New York Post had incorrectly dated the pictures 1995, which raised questions about whether she had worked in the United States before possessing a work visa. “I spoke to the lawyer that did the visa, my understanding is that she came in ’96,” he said, adding “I had nothing to do with the green card.”

In a subsequent email, he wrote: “If u write something about model taking picture w/ nothing on Yes this is part of the business is like An actor in movies that as an intimate scene …. I Am sure POTUS Regan or Governor Svarzeneger [sic] do have intimate scene in their movies.”

In 1998, Mr. Zampolli introduced the future couple, but it was not his lone stab at matchmaking. In 2006 Mr. Zampolli, then the president of ID Models, arranged a meeting between Mr. Burkle and a reporter from Page Six, the gossip page where Mr. Zampolli boasted that he and his models had appeared “close to 54 times” in one year.

Mr. Zampolli suggested to Mr. Burkle that a better relationship with the newspaper could improve his treatment. Among other items, Page Six infuriated Mr. Burkle by describing him as someone known for flying around on his Boeing 757 with models and considering buying a modeling agency that he would perhaps run with Mr. Clinton.

Mr. Zampolli organized the meeting. It didn’t go well, with Mr. Burkle ultimately alleging to the F.B.I. that the writer had tried to shake him down in return for better coverage.