My City Hall rabbis Kiley and Tidman also arranged for me to meet a guy named Jack Connors, who along with three partners had founded Hill Holiday, an advertising and communications firm, several years earlier. Jack was a confidant of Mayor White, an informal but influential advisor on communications strategy. If I was going to be in the press office, I had to have Jack’s blessing.
For the second time in a few weeks, I put on new underwear and a new shirt, jacket, and pants that finally fit. I set off anxiously to meet someone who was so far above me in terms of polish, panache, and duende, I might as well have been a scared mouse in the corner. When I met Jack, I again had the feeling that the person I was meeting had appraised me and concluded, “you’ve got to be kidding me.”