"His style in the press conferences was interesting. Not terribly popular with the reporters (too much a contemporary, yet too difficult to understand ...), he carried himself nonetheless with a cool grace which seemed indifferent to applause. ... There was a good lithe wit to his reponses, a dry Harvard wit, a keen sense of proportion in disposing of difficult questions ... Yet there was an elusive detachment to everything he did." (PP, 45)
Back in Kennedy's day, public officials would hold press conferences with their mistresses at their side. The journalists simply wouldn't comment. The press conference itself would not be transmitted or recorded in its entirety. The journalists would filter out the parts that were to remain between the official and the journalist.
So we're seeing an important difference in the rhetorical conditions faced by Kennedy and Obama. But we're also seeing a real difference in style. Kennedy was "too much a contemporary, yet too difficult to understand". Obama, who we must say is well-liked by reporters, is also a bit too contemporary. In fact, he may be younger in spirit than most of the Washington press corps. He may even be less square.
But this will get him in trouble it seems. Jon Stewart could never be president because he would not be able to detach himself from a comedic resonance. Once the word "living" had been (inadvertently) emphasized, popular culture sends you looking for a reference to the occult. As it turns out, the White House is associated with the occasional séance. (Hillary Clinton is said to have conducted one or two in her time.) Obama could have left it at that. He could even have said, "Unlike some of my predessors..." But he accidently (and apparently wrongly) took a good-natured, chummy-with-the-press-corps jab at Nancy Reagan by name.
In the room, that would not have been a problem. But on "national TV" it looks terribly mean. (Jon Stewart is not on national TV in that sense: he's got a "demographic".) If he had been Kennedy, it would have remained between Obama and the reporters.
I like this gaffe because it explains why Obama reads prepared statements so often. When he's in public, he's exposed. More so than presidents have been in the past. As a symbol of this, remember that he held his acceptance speech behind bulletproof glass. I found his delivery too detached. He did not connect with his audience, he did not share his feelings of victory with them. He did not, finally, seem happy. But he had also just felt, I think for the first time, the full chill of his Secret Service protection. It descended on him like a cheese bell.
Off his script, Obama spoke not like a late-night talk show host but like a Harvard professor who watches late-night talkshows and tries to be funny in the classroom. "If one had a profound criticism of Kennedy it was that his public mind was too conventional, but that seemed to matter less than the fact of such a man in office because the law of political life had become so dreary that only a conventional mind could win an election" (PP, 49). So we must hear about the puppy (has anybody thought compare this theme to Checkers?), but, it must be granted, in a manner supported by a pretty crisp sense of irony. There is something cooler about a president who likes to talk about basketball than one who likes to talk about football, but it's still sports. It's conventional.