I recognize several of those things in myself, now when following the political life of today closely. It's kinda too much, and when people you know won't believe you, it's even worse.
Here's some excerpts from one of his books, Heartland:
So then I went to the dinner. It was the first time I met Kennedy, standing there with those laser-beam blue eyes, looking very quizzical. He was curious about me, my age, my political posture. Shook hands, told me he appreciated what I was doing, and asked, "Have you got any more one-liners? This looks like a rough crowd." Bobby just sat on the sidelines and waited. I suppose that even though he was emotionally as loyal as he was to his brother, he was waiting his turn. In the crevices of his mind he was a lot like Hamlet. He must have wondered why it was his lot in life to break the doors down for this guy and to cut all the corners and be an outlaw of sorts and then be rewarded by people saying, "Jack, you're great, but I can't stand that rat who works for you." There had to be a jealousy—which I thought he contained admirably.
Afterward, we went to Kennedy's plane, parked at L.A. International Airport. He was on his way to Palm Springs with Sinatra and he called me to join him on the plane. When I got aboard he asked me to sit up front. The Senator said, "Where was Paul Ziffren four years ago?" I said, "I guess with Stevenson." He said, "Of course, a logical position," and I said, "How do you arrive at a logical position?" and he said, "You just think in terms of survival." Everybody was drinking Bloody Marys. Then Kennedy put his finger to his forehead, pensively, and he said, "Tell me, why do you like Castro?" He never let his ego stand in the way of his curiosity. I told him of my admiration for Castro and that a revolutionary, I thought, appealed to all Americans—well, not quite all, for Americans view South American revolutionaries as a joke, the Russian revolutionaries as a horror, and the American revolutionaries as heroes.
Kennedy asked me about a joke I told on television about him. He was grilling me, knowing the answers, but insisting on my telling them to him literally. I had said on TV that his father had said, "I'm putting you on an allowance. You're not allowed one more cent than you need to buy a landslide." "What does that mean?" Kennedy asked, relentlessly. I told him it meant his father was rich, for one thing. "How much do you think he has?" he asked. So I made a snap decision and said, "Four hundred million." He looked at me as if I were retarded and asked if I knew how much the Rockefeller brothers were worth. "Liquid," he said, "about ten billion." Then he looked at me and said, "Now, that's money!"
More excerpts here:
http://www.maebrussell.com/Articles%20and%20Notes/Heartland%20excerpts.html