I’ve always said that “thumb pointing” comes from sexual “fisting”. The set and angle of Clinton’s fist when he does the “thumb pointing” thing is exactly like the forearm and clenched fist fisting dildo you can find at any of your popular adult book/DVD/toy shops.
Bill was just conveying his desire to “fist” America whenever he used the gesture. I think it’s charming.
Here’s a link to a youtube video of a Kennedy speech, he makes the fist gesture described by the OP, starting at about :20, when he says “That goal …” Later, he switches to a fist with more of a pronounced point, when he says “That challenge …” (In case I mess up the youtube link, you could search for “John F. Kennedy 's speech (Apollo program)”)
To echo Mater Sammich, I have often heard that Clinton intentionally created a style similar to JFK’s. I don’t know if his intentions can be proven, but there’s no doubt that Clinton (based on his age if nothing else) would be extremely familiar with Kennedy’s public speaking persona and the Kennedy connection was played up very heavily in his first presidential campaign.
I really don’t think Kennedy was all that PC, either.