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There were about 30, all Mexican nationals desperate to avoid deportations that would separate them from their families. Living in Illinois, they appealed for help from their new U.S. senator, Barack Obama.

He turned them down.

It was one of the first times Obama could have used the power of his office to help defer the removal of immigrants who were in the United States illegally. Eight years later, with his powers magnified as president, such a decision is upon him again, this time with the status of millions of immigrants at stake.

That episode in 2006 represents just one early marker in Obama's complicated history with the politics of immigration. The son of a Kenyan immigrant, Obama has been embraced and scorned by immigrant advocates who have viewed him as both a champion and an obstacle to their cause.

Now, perhaps paradoxically, in their anger over his delay of executive actions that potentially could give work permits to millions of immigrants living illegally in this country, these advocacy groups also hold out hope that when Obama does act, he will be aggressive and leave a mark for posterity.

"Some of the hard feelings could be forgotten at the end of the day if he acts boldly," said Janet Murguia, the president of the National Council of La Raza, a leading Latino advocacy group.

Obama's record on immigration, however, is one of caution and deliberation punctuated by moments of determination amid some broken promises. With the president delaying executive action until after the November congressional elections, some Democrats worry that expectations have been raised beyond what he can deliver.

"If they weren't sky high before, they are now," said Jim Manley, a former top aide to Senate Majority Leader Harry Reid, D-Nev. "I'm not convinced they will meet the expectations of the Hispanic community."

White House officials say the delay will not affect the scope of what Obama intends to do. And they play down suggestions he is looking to build his legacy with the decision.

"The goal is going to be to do as meaningful a package of reforms as is available to the president through his executive authority," White House communications director Jennifer Palmieri said. "I don't think that is going to manifestly change from September to when we do this later this year."

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Obama and Immigration: High Hopes, a Mixed Record