Politico reported Tuesday that two of Obama's top advisers were on the wrong side of the emotional issue six years ago when the Clinton administration forcibly took and then sent Elian to his father in Cuba.
Eric Holder was a deputy attorney general at the time while Greg Craig was a lawyer representing Elian's father.
"I don't think that the Cuban-American community is going to put their trust in Obama in terms of Cuban politics," said Jaime Suchliki, who runs the University of Miami's Institute for Cuban Studies.
Politico said Obama's appearance in Miami last week drew picketers and Miami Mayor Manny Diaz, an independent, refused to endorse Obama.
Some observers see Elian Gonzalez as a higher-profile issue in the 2008 election now that Fidel Castro is no longer in power but Democrats are hoping that younger Cuban-Americans will look to the economy and other issues as their primary campaign concerns.