In your questionable zeal to make Sean Hannity appear more foolish (he really does not need any help), and obfuscating your motives through charitable giving, you have succeeded in further trivializing torture.  You are aiding in turning water-boarding into a parlor game.  No matter how many seconds Hannity would survive the water, it is unlike any water-torture our "enemies" would have received, in that they would never know it would stop.  You got suckered into a game, Mr. Olbermann, and the result will be that waterboarding will become mundane, even thinkable.  It should not be; it should remain a thought and picture that we should all recoil from. 

  You should not want him or anyone waterboarded, nor should the gleeful commenters on blogs discussing your offer.

  Even the debate on whether or not torture "works" is rather beside the point.  That cannot be proven; there will be opinions everywhere, and no objective truth.  It essentailly does not matter; it is against our laws, against international law, and it is wrong, and immoral.  Stop playing cutesy with fox news pundits; you degrade yourself, as well as the issue.  What you are doing smacks a little of revenge, which is the one mostly unspoken motive of torturers and the authors of torture.