If President Obama lost to Romney in November, do you think there would be any possibility down the road for him to pull a Grover Cleveland and win the presidency again? He is a relatively young man and still the most charismatic Democrat at a national level. Could he plausibly win again down the road or would the narratives of him as a defeated one-termer and party pressures make it too much of a challenge?That's a fun question, isn't it?
Let's see. The defeated (or early retirement) presidents since the two-term limit were Johnson, Ford, and Carter. What do they have in common? Johnson resigned in the face of a nomination battle; Ford and Carter barely managed to get themselves renominated. So none of them is really a good comp for a defeated Barack Obama. Going back before the 22nd amendment...Truman, too, was hardly a lock for the nomination had he chosen to run in 1952.
I don't really know anything about Hoover's renomination in 1932, but of course his defeat in November was a wipeout. Coolidge presumably wanted to stay retired. Wilson couldn't have had the nomination in 1920 even if he wanted it (which he probably did). Nor could Taft, I assume, if he had tried in 1916.
That gets us back to the closest thing to Cleveland's comeback, the Teddy Roosevelt effort in 1912. And before that...well, I guess before that is Cleveland himself.
So there's really nothing at all similar. The defeated or retired presidents in the 20th century either had serious opposition within their party or lost a blowout or really wanted to be retired. There's no way of knowing whether Obama would want a comeback, but assuming the presidential race remains close, he would pass the other two tests.
On the other hand. Michael Dukakis didn't do that badly, but I think Democrats were pretty united against inviting him back. The same is probably true, although not quite as definitely, about John Kerry and Al Gore; it's hard to tell how much of their choice not to run again was personal and how much was a calculation of the politics. Hubert Humphrey came close, but didn't quite win the 1968 nomination. There's also, for whatever it's worth, the Democrats' habit of nominating first-time candidates (in every recent open nomination except for VP Gore and former VP Mondale, and Mondale hardly ran in 1976). So there's at least a bit of evidence that the post-1968 Democratic Party doesn't like retreads.
Put it all together, and the obvious answer is: who knows? I wouldn't entirely rule it out, though. Presumably the conditions that would make it most likely would be a very close loss in November, perhaps even one with some controversy involved, followed by a further economic downturn; it's hard to see Obama as a strong 2016 candidate if the economy does well for President Romney (of course, it's hard to see any Democrat winning in that case).
I suppose it's also worth mentioning that he wouldn't necessarily have to do it in 2016, when he'll be 54. In 2028, he'll just be a little bit older than Mitt Romney is now. But presumably his best chance would be losing a close election this fall, then Romney winds up an unpopular president, and then running next time.