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If Wikileaks hasn’t already gone too far, what should be done to make sure the “media insurgency” Web site doesn’t? Or should any restraints be placed on such activist whistle-blowing at all?

These are questions that come to mind as we read daily news stories about the rogue site’s latest release of classified materials. From conspiracy theories about Apple Computer’s refusal to support the Flash media platform, to video of Afghan airstrikes gone wrong, Wikileaks seems to have a bottomless supply of content that traditional media don’t or can’t use. The problem is determining if this a good thing for public awareness, or a bad thing for privacy and national security interests?

At the moment the question may be academic, as I cannot connect to Wikileaks.org (apparently run out of Iceland). And I suspect no one else in the continental U.S. can either. Or perhaps this is all part of the “stealth journalism” approach, and the site is just lying low for a while. Wikileaks Australian-born founder, Julian Assange, is also hard to put a finger on. He has no fixed address, no known offices, and no paid employees. Assange is a notorious hacker who, as a teenager in the 1980s, caused national governments in Europe and North America no end of pain. In a book he co-authored he implored other hackers to tread lightly but decisively by merely sharing stolen information without doing any damage to the systems they invade. Nice of him. A thief with a conscience; a sort-of digital Robin Hood.

Assange and his Web site present a tough problem to people like yours truly: we want transparency in government and commerce; we want nations and corporations to be held accountable for their sins; but at the same time we don’t want to step on anyone’s privacy rights, or to compromise valid security efforts or place our security and military personnel in more jeopardy than they already face.

Twenty years ago I would have not only approved of Assange’s project, I might have joined him. Today I see things as being a little more complicated than a purely “us-and-them” political struggle. So far Wikileaks has been careful to avoid releasing material that might directly harm anti-terrorist operations or military personnel – as far as we know. There’s the problem: are we or Assange qualified to make that determination?

Of course the military and intelligence communities see any leak of classified material as harmful, whether to their jobs or their personal reputations. So they aren’t the best judge of what is transparency and what is crime. And in the absence of any structured way to approach such judgements we are left with things as they are: Wikileaks is safe until it crosses someone’s perceived line between journalism and espionage.