The chief way that two seem alike to me is that their need for public adulation drives them to behave badly. And they seem obsessed by the predecessors who continue to haunt them, cool men who earned the public's fascination without begging for it.
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Nixon, of course, refused to let go of JFK. They knew each other well and were friendly enough when they both arrived in Congress. As Senators, their paths began to diverge. When 1960 happened, Nixon bitterly resented losing The Presidency to a man whose glamor he couldn't match. Then JFK became a martyr, and there's no winning against the dead. Yet Nixon couldn't end the rivalry. At one point, JBKO pointed out to him that he would do things her late husband never would, like grow old with his wife and give his daughters away at their weddings. But Nixon couldn't see it that way. He let envy eat him alive. In Being Nixon, Evan Thomas writes of President Nixon ordering a low-level bureaucrat fired simply because she kept a portrait of JFK framed on her desk. (His aides secretly refused to do it.) In The Final Days, Woodward and Bernstein give us a Watergate-era Nixon drunkenly arguing with Kennedy's White House portrait.
So what is it about Obama and Kennedy that their successors can't escape? Is it the easy elegance? Their Ivy League educations? The natural wit? Their acceptance among the media elites?
Or is it the sunglasses?
I'd love to hear someone like Tim Naftali weigh in on this. Prof. Naftali knows the Cold War and Nixon so well, and he's a recognized expert on Watergate, which has landed him on CNN a time or two since the Trump/Russia investigations began. (Prof. Naftali, if you read my blog ...)