Four former presidents have resought the White House (and more have tested the waters). Only Grover Cleveland, in 1892, succeeded. Would Obama do the same? Born in 1961, he could be a viable candidate not just in 2016 but, theoretically, in any election through the 2030s. "It's less driven by his age, and more by the margin of defeat," says Fleischer. A landslide loss in November 2012 would rule him out forever. "But if it's a close loss," Fleischer says, "Barack Obama is gonna get asked regularly: 'Are you running?' 'Will you rule out running?' 'Has he been Shermanesque yet?'?"
If Obama were tempted to campaign again in 2016-and here the hypotheticals really begin to pile up, although they are intriguing-the primary battle could be every bit as pitched as a general-election rematch. Vice President Joe Biden has repeatedly refused to rule out a run, telling NBC this month, "I am never ready to close the door on anything." And there's always the possibility of another Hillary Clinton candidacy. The secretary of state said in October that she would not run again for president, but her husband enjoys fanning the flames of speculation. "You'll have to ask her," he said this fall. "If she wants to come home, I'll be happy. If she wants to serve, I'll be happy. But she has to decide that." Clinton would be 69 in November 2016; Biden would be 73. Obama? Just 55.
Annual Earnings: $400,000
Likelihood: Don't count on it