The moral, I think, is that some things are better left alone. Such as Shepard Fairey's original Obama poster.
Unfortunately, his make-over for TIME seems to play on the Machiavellian idea that a clever, charismatic and left-wing Obama (when was the last time TIME fronted a peace sign?) exploited a couple key issues, turned himself into a pop icon, and scored the presidency out of it.
Reading the pop art cover re-do left-to-right, I see an upward-looking guy who mostly took opposition to the Iraq War (occupying about the top quarter of the illustration) and more talk about alternative energy, wrapped those issues in a patriotic package, and then leveraged the early support of the peace movement (lower right) to curry favor -- in light of the public's profoundly low regard for Washington -- to score enormous cash from the teeming hordes (see crowds right of the dollar sign ... and lower left, too).
What this shallow illustration seems to bypass, however, is how Obama really won the presidency, which -- beyond all the packaging, and the cultish fans, and the war issue -- was his demonstration of judgment (on issues as diverse as talking to foreign leaders; being more assertive regarding Pakistan; and not finessing the scale of the economic meltdown) as well as his calm and steadiness under fire.
Besides TIME's own Obama-envy and the blatant play to a younger demographic, the illustration, as much as anything, seems to telegraph Fairey's own desire to cash in on the original artwork -- another reason for the poster-within-the-poster on Obama's collar just under his chin, not to mention the enormous dollar sign.
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(illustration: Shepard Fairey. Cover, TIME's Person of the Year issue. Dec. 29, 2008)