From 2006, an interesting take:
If by some miracle [Obama] hits the lottery and wins in ’08, well, then it is win-win-win. He’s a young man with a future. But the future recedes. He needs to run now. And lose. And win by losing.
Context here:
When just a week ago Barack Obama showed a bit of ankle and declared the mere possibility of his running for the presidency, the chattering classes swooned. Now that every columnist in the country has given him advice, here’s mine: He should run in ’08. He will lose in ’08…
And the loss will put him irrevocably on a path to the presidency. Obama’s political challenge is to turn his current fame and sizzle, which will undoubtedly dissipate, into something concrete. In physics, it’s the problem of converting kinetic energy into potential energy: Use the rocket fuel behind his current popularity to propel him to a higher national plane from which he would eventually move almost laterally to the presidency….
Obama should be thinking ahead as well — using ’08 to cure his problem of inexperience. Run for the Democratic nomination and lose. He only has to do reasonably well in the primaries to become such a compelling national figure as to be invited onto the ticket as vice presidential nominee. If John Edwards, the runner-up in ’04 did well enough to be made running mate, a moderately successful Obama would be the natural choice for ’08.
The Dish 