[Scott McClellan is] a knuckleheaded Socrates, each day struggling and failing to talk his way out of a paper bag.

It's this verbal haplessness that has made Scott McClellan—a pleasant, low-wattage, old-before-his-time young fellow, with, at 38, a wife, no children, and "two dogs and four cats"—the living symbol of this White House's profound and, perhaps, mortal problem with language and meaning.
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He's what the Bush people like to call a straight shooter. Very much the kind of young person whom older people like (this is a certain sort of high status in politics in general and in southern politics in particular—dweeb as acolyte).
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My guess is that nobody in the inner circle thought it very important that he couldn't talk, that he had to plod and often struggle through every sentence. Not being able to talk—not being quick enough and facile enough to shape language to your precise and urgent needs—might even have been a further sign of his straight-shooter qualities.
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His lack of verbal acumen, his lack of dexterity with a subordinate clause, becomes another part of the way to control the White House message in a White House obsessed with such control.
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His inability to finesse the administration line, to tickle its logic, to prettify it, to seem smart about it in the least—and with virtually every one of his prevaricating and dissembling and truth-avoiding utterances becoming the morsels of the daily blog diet—means the media has to struggle even more to justify how it ever believed these num--skulls.
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It is so bad, and so constantly public—every misspoken word, every stutter, every repetition, repeated mercilessly across the information universe—that he can only hope that it's gotten bad enough for him to get a sympathy vote.
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[The Administration's] whole theory, to the extent they theorize, is to keep it simple, stupid—in fact, to mock the people who make it complicated. The problem is that Scott McClellan isn't really a bully. He's rather a pantywaist.