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As the lead piece in a Colloquy entitled The First Amendment and the Paratroopers' Paradox, this article argues that today's free speech theory is largely grounded in 18th Century fears of government's tyrannical censorship. This theory is ill-equipped to deal with a distinct tyranny in 21st Century America, a tyranny playing upon the public's insatiable appetite for amusement. Those who venture to develop free speech principles to suit a new cultural environment are the First Amendment paratroopers of our time, the ones who realize that we cannot retain our old constitutional prerogatives in a transformed world. The Paratroopers' Paradox: To save itself, the traditional First Amendment may destroy itself.