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. 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.”

The 2006 incident with the immigrants seeking to avoid deportation illustrates Obama’s past reluctance to act unilaterally and calls attention to the on-and-off relationship he has had with leaders in the Latino community.

As Obama recalls in his book “The Audacity of Hope,” a group of Chicago community advocates visited his office seeking legislation to legalize the status of that small group of Mexican immigrants. Obama didn’t want to provide special dispensation to a select group and sent an aide to decline the request, leading to a confrontation.

That year, Obama also angered Latino leaders when he voted to erect a 700-mile double fence along the U.S.-Mexico border. The measure passed the Senate 80-19, over the objections of many Latino groups who saw it as an enforcement-only alternative to a comprehensive immigration overhaul.

Over time, Obama would build a varied immigration record:

—He backed compromise legislation in 2007 from Sens. Edward Kennedy, D-Mass., and John McCain, R-Ariz., to overhaul immigration laws. Whether his support for a labor-backed change to the legislation contributed to the bill’s demise remains a point of debate.

—During the 2008 Democratic presidential campaign, Obama took the side of pro-immigrant forces in supporting driver’s licenses for immigrants living illegally in the United States. That stand distinguished him from Hillary Rodham Clinton, who opposed them.

—Obama galvanized Latino voters with promises to take up an immigration overhaul during his presidency’s first year. But once in office, he backed off to deal with the recession and launch a health care overhaul.

—Under his watch, deportation numbers began to rise. Immigration groups protested; Obama argued he could not act unilaterally to reduce deportations.

—In 2012, as he campaigned for re-election, his administration announced a plan to defer deportation for certain immigrants who entered the country illegally as children. Since then, the program has deferred deportation and provided work permits for nearly 600,000 immigrants.

—He backed bipartisan comprehensive immigration legislation passed in the Senate in 2013 and held out hope the Republican-controlled House would follow. This past June, Obama was finally convinced the House would not vote, and he promised to act on his own shortly after summer’s end.

—This month, Obama decided to wait until after the elections, saying he worried his actions would be undermined by campaign politics and damage any prospects of future legislation.

For Obama’s executive actions to be embraced by Latino and immigrant advocates, Murguia said, the number of people helped must far surpass the number of deportations under his administration — 2 million-plus, already.

“If he does 3 million or less, then years from now it could be said he deported as many people as he protected,” Murguia said.

White House officials caution that without a change in the law, Obama’s actions are limited.

“Whatever we do is going to be imperfect,” Palmieri said, “and is not going to be as big as we need.”

(AP)