Here's a possible answer, and it's something you see again and again in today's pundits. It's not enough for them to be getting six-figure salaries to spout their opinions; to be feted at cocktail parties; invited on TV chat shows; sucked up to by star-struck underlings; and constantly told by colleagues how incisive and witty their latest effort was. No, they also need to feel that they are brave and heroic in holding their opinions, too.
To look into the mirror and see a brave and heroic pundit staring back, of course, you need to flatter yourself into believing that you're challenging entrenched ideas and the people who hold them in some way, even if you aren't. This impression can be created in several ways. One is to simply dream up a whole class of people, claim they hold "extreme" opinions based on nothing at all, and set yourself up as a lonely warrior against them -- preferably while standing shoulder to shoulder with other lonely heroes of moderation like John McCain and Joe Lieberman. That's David Broder's preferred approach. Another way is to dream up a whole series of nefarious but nonexistent motives driving colleagues' opinions, so that you can deprive those colleagues of credit for those opinions, and position yourself as, again, braver and more heroic than they are -- even though you agree with them. That is Klein's approach -- and I submit that at bottom it's all about vanity.
Klein issued a challenge in his post that has already been deftly parried by Boo Man. So here's a challenge for Klein: Back up your arguments with facts and evidence. Produce one example of someone whose comments betray the fact that they're tacitly rooting for American failure. Quote this person. Explain why this person's quotes should be interpreted that way. If you manage to get that far, then maybe consider finding a second example, and even a third. That doesn't sound all that hard, does it?
Of course Klein had a chance to be truly heroic back in the Fall of '02 and Spring of '03. He could've used his prominent soapbox to be one of the few major pundits to stand against the war. While he claims now to have been opposed to it, his public record doesn't really reflect that. Sure he had some misgivings and made the shockingly bold suggestion that Al Gore may not be entirely insane, but he didn't really come out against the war.
There were few heroes with access our mainstream media then and Klein missed his chance to be one.