Probably not well.
History likes to divide presidential analysis into two camps, at least in the Czar’s experience.
Sometimes history immediately dumps on the guy: Carter, Fillmore, Pierce, and Buchanan, for example, generally were excoriated while they were still sliding the key under the mat at 1600. One-term presidents, not surprisingly.
Then comes the second camp: usually, but not always, two-term presidents. These guys are analyzed over a longer period of time. If they were recent Democrats of course, the first-to-publish histories are fawning hagiographies about how wonderful everything was. If they were recent Republicans, naturally, we see books demonizing them as child stalkers and cat stranglers or worse.
After a few years, the memoirs come out from the former aides. We learn what jerks and fools the saints were, and how the demons were really caring guys who did a lot for various minorities, and on and on.
To pick a couple, we learned in the late 1970s what a lunatic jackass Lyndon Johnson was in private, and how if any of that had come out in the 1950s, he never would have been president. We also are discovering what a keen intellect George W. Bush really had, and how he managed with great charm and effectiveness behind the desk.
Anyhow, the Czar expects that the Obama presidency will be viewed in a similar manner to the Wilson presidency. No, God forbid that he should suffer illness and be hidden away and manipulated by his wife—the Czar doesn’t mean his presidency will be the same. Just that we will need to sit through 20 years of happy memories, sighs about the bad Republicans, propagandistic biographies, and books with charming titles. Yes, there will be futile fantasies about faces on Rushmore, lavish temple-like memorials on the Mall, and the O logo on the new dollar coin. But this will quickly and quietly fade, with a handful more Barack H. Obama Elementary Schools and the Obama Expressway connecting two random exits together on an existing interstate.
Then the alternative histories will come out, and casual American readers will be shocked to learn that many of the best accounts of what a screwed up presidency this was were written while he was president. The first couple will pop up as best sellers and in 2035, you will see the definitive tome come out at your library, explaining chapter-by-chapter about the corruption, meanness, pettiness, arrogance, and all the other things you see documented at our site as well as thousands of others.
And in the longer reach of history, like Wilson, we will learn what a snake the guy really was, and how he had little problem threatening personal liberty at the expense of his own lust for power. How he viewed himself as beyond the pedestrian laws, and how enemies needed to be punished. And in 2050, like a ways back when kids found all their grandparents’s Wilson shrines, memorabilia, honorific sheet music, and other souvenirs of a different era stuffed in a forgotten basement box, there will be a pause of embarrassment. Why were you all so nuts for this guy?
The sad truth is that your grandparents could at least sigh and explain that Wilson accomplished a fair amount while President, bad and good. Today’s future grandparents will have a really tough time explaining Obama. “We voted for him because he was so good-looking.” And the kids will look at him and ask “Really?”