Rabbi Irving Greenberg, who was the president of the Steinhardt Foundation for Jewish Life for a decade, said he repeatedly rebuked Mr. Steinhardt for using belittling language toward both men and women. That tension was a factor in his deciding to leave the job in 2007. (After this story published, the Steinhardt family and foundations released a statement, which can be read here.)

Mr. Steinhardt could be harsh with men, but his comments to women focused on their appearance and fertility, Rabbi Greenberg said. When Mr. Steinhardt talked to women, the rabbi said, “the implication was that they were not on par with men.”

He said that the comments were made in a bantering, not threatening, tone and that he never saw Mr. Steinhardt directly proposition anyone. Still, he said, “I understand that the women felt more shaken or threatened than I recognized at the time.”

Ms. Katz said she was hoping Mr. Steinhardt would become a funder of her work at Hillel when she met with him in his Fifth Avenue office in 2015 to interview him for a video Hillel had commissioned about Jewish entrepreneurs. But she said that as the filming got underway, he repeatedly asked if she would have sex with the “king of Israel,” which he had told her was his preferred title for the video. He then directly asked her to have sex with him, she said.

When she turned him down, he brought in two male employees and offered a million dollars if she were to marry one of them, she said. After the filming ended, Mr. Steinhardt told her it was an “abomination” that a woman who looked like her was not married and said he would not fund her projects until she returned with a husband and child, said Ms. Katz, who has not previously spoken publicly about the incident.

Through his spokesman, Mr. Goldin, Mr. Steinhardt denied most of the details of Ms. Katz’s story and said he did not “proposition” anyone. Mr. Goldin said Mr. Steinhardt was not aware that Ms. Katz was courting him as a donor when they met.

Ms. Katz said she was shaken and reported the comments the next day to Eric D. Fingerhut, the chief executive of Hillel. He apologized and promised that she would not have to meet with Mr. Steinhardt again, she said. Hillel confirmed generally that Ms. Katz reported the incident but would not comment on specifics.