According to her daughter, Fritzi, Howard became involved with Castro and viewed herself as a grand player on the stage of history. In an article for Politico detailing their relationship, Peter Kornbluh describes Howard's role as a liaison between the United States and Cuba as "intimate diplomacy," explaining that "her role as peacemaker was built on a complex, little-understood rapport she managed to forge with Castro himself – a relationship that was political and personal, intellectual and intimate.” In order to continue the reconciliation agenda, she set up a meeting between UN diplomat William Attwood and Cuba's UN representative Carlos Lechuga on September 23, 1963, at her Upper East Side New York apartment, under the cover of a cocktail party. With Howard's support, the Kennedy White House was organizing a secret meeting with an emissary of Fidel Castro in November 1963 at the United Nations—a plan that was aborted when President Kennedy was assassinated in Dallas on November 22, 1963.