Andrew M. Cuomo was about to marry. Donald J. Trump was about to divorce. And the future governor of New York and the future president of the United States crossed paths at Mr. Cuomo’s bachelor party.

The year was 1990 and Mr. Cuomo, the son of Gov. Mario M. Cuomo, was merging with the Kennedy clan — “Cuomolot,” the union was called — just as Mr. Trump was splitting with Ivana Trump in a typical tabloid spectacle.

Mr. Trump did not attend the party, but he sent a lighthearted video clip that played at the Manhattan bar where Mr. Cuomo’s friends and political luminaries had gathered.