Nine months ago, the new Homeland Security secretary, Jeh Johnson, received a request from the White House. President Obama wanted him to personally take on perhaps the administration’s toughest political assignment: looking for creative ways to fix America’s immigration system without congressional action—or executive overreach.

Just four months into the job, Johnson had been prepared to take on tough security issues: Bombs on planes. Deadly diseases. Radical Islamists carrying U.S. passports. As the Pentagon’s chief counsel, Johnson had routinely dealt with contentious national security matters, finding himself in the midst of sensitive political fights like whether and how to close Guantanamo Bay, allowing gays in the military, and the rapid expansion of America’s killer drone program.


He wasn’t prepared for a crisis of purely political making.

Just days earlier Obama had been labeled the “deporter in chief” by a top Hispanic leader and ally, furious over the inaction by a president who seemed trapped between the demands of his supporters to allow millions of long-time residents who lacked documentation to stay in the country, and the seemingly endless foot-dragging of Republicans.

That request to Johnson would prove critical: a moment when the president set on the path of a much more ambitious change than the narrow changes in civil enforcement policy he and his aides had initially explored. In the remaining months of 2014, Obama would come to support a sweeping executive action to allow millions of undocumented immigrants to stay in the country, as Congress lurched from willingness to consider changes to strained immigration laws to refusing to tackle the issue at all. Meanwhile, interest groups from the Congressional Hispanic Caucus to the Business Roundtable, from K Street’s shrewdest lobbyists to the most hard-nosed union bosses, intervened to try to shape the direction of the order.

At several key points, Obama wavered under pressure from members of his own party, worried about an electoral collapse that happened anyway when the votes were counted in the midterm elections earlier this month. Throughout, Johnson worked, largely in secret on the grand plan that finally became public this week, convening a small group of former Capitol Hill aides with expertise on immigration to work with Homeland Security officials to draft a policy that all expected would provoke not only fierce opposition from conservatives but from liberals who thought Obama should go further. It was a consuming task: in all, sources said, the immigration issue ate up fully half of the Homeland Security secretary’s time in recent months, with Johnson —a high-powered corporate attorney in his previous life — writing the final presidential memorandum himself.

By the time Obama went before the American people to unveil his plan in an Oval Office speech to the nation Thursday night, the White House and DHS had exchanged dozens of drafts and endured months of starts and stops, punctuated by a sharp electoral defeat for their fellow Democrats. Still, they went forward, with the president finally telling aides of his decision in the Roosevelt Room of the White House on Monday night.

Johnson, for his part, seemed anxious to be done with a journey he portrayed as a political lesson.

“I was new to immigration law and policy…when I came into this job,” Johnson said this week. “Before that it was law of armed conflict, national security fiscal law. I’ve been disheartened and disappointed with how volatile the issue has become in American politics. I hope that people will look at immigration reform from a common sense point of view, what makes common sense, what’s practical, what’s pragmatic.”

Summer of miscalculations

Three months after Obama’s first overture to Jeh Johnson, Republicans had not given up on the idea of an immigration plan of their own. At least, some argued, there was a political opening to forestall any independent action by the president. June 12 was the day that Rep. Mario Diaz-Balart (R-Fla.) planned to unveil to House leaders an immigration bill that, he was convinced, many Republicans could get behind.

IMMIGRATION POWER PLAYERS White House Jeh Johnson, secretary of Department of Homeland Security: Barack Obama tasked Johnson with fixing the immigration system. He became so engrossed with the job that he wrote the final legal memorandums for the executive order himself. Neil Eggleston, White House Counsel: Eggleston was a lead negotiator for the White House. He was in meetings with the stakeholders before Obama announced the July pivot to executive action. Obama called Eggleston ‘his guy’ on immigration reform, and he was. Esther Olavarria, senior counselor to the secretary: The former aide to Sen. Ted Kennedy, who advised the Massachusetts Democrat on immigration, served as the point person for Capitol Hill and outsiders at the Department of Homeland Security. Cecilia Munoz, director White House domestic policy council: Worked closely with the Hispanic pro-reform groups and helped build out the coalition of supporters to include civil rights groups and others. Valerie Jarrett, senior advisor to the president: Obama confidant tasked with wrangling downtowners and advocates to stay on message. Eric Holder, Attorney General The Justice Department played a key role in the review to ensure the executive actions are legally defensible, and has a point-person in place to coordinate its response to the anticipated legal onslaught. Capitol Hill Red-state Senate Democrats: Nervous about the political impact on their reelection bids, red-state Democrats such as Kay Hagan of North Carolina and Mark Pryor of Arkansas called on the White House to stop executive action on immigration. Obama did, but most lost their races anyway. Sen. Angus King (Ind.-Maine): The Maine independent, who votes mostly with Democrats in the Senate, called the White House chief of staff over the summer hoping to persuade Obama not to take executive action. The call from an ally sent the White House into crisis mode. Rep. Mario Diaz-Balart (R-Fla.): The Florida Republican worked aggressively this spring to pull together a bipartisan immigration reform deal, but his efforts were thwarted by Rep. Eric Cantor’s primary loss and the border crisis over the summer. Rep. Luis Gutierrez (D-Ill.) Perhaps the loudest voice in Congress for immigration reform, Gutierrez repeatedly criticized Obama over deportations and pushed for executive action for months — keeping the issue in front of the president. Capitol Hill Janet Murguia, President and CEO, National Council of La Raza: Murgia called Obama the “deporter in chief” at a March gala, setting off the events that ended in executive action. Mary Kay Henry, President of the Service Employees International Union (SEIU): Henry is a key labor advocate who pushed Obama to stay the course and move ahead with executive action before the election. Richard Trumka, President AFL-CIO: Trumka, who heads one of the most powerful labor unions, made statements going back to 2013 that Obama should take executive action on immigration reform. Behind the scenes, the union was for delaying executive action until after the election.

For more than a year since Obama’s re-election, in which Hispanic voters had turned out in unprecedented numbers to vote against a Republican nominee who came out hard against undocumented immigrants (Mitt Romney even memorably called on them to “self-deport”), Republicans had flirted with — and invariably backed away from — proposals for comprehensive immigration reform. Any bill that could be seen as granting legal status to people who entered or stayed in the country illegally was a non-starter for many conservatives. Senate Republicans like John McCain and Marco Rubio had eventually, carefully, stuck out their necks just far enough to get a comprehensive reform bill through the Democratic-controlled Senate. But the Republican-controlled House was another matter. GOP leaders saw the need for some sort of action, but rank-and-file conservatives were deeply skeptical or outright opposed.

Enter Diaz-Balart, the Floridian whose Hispanic background and solid relationships with conservative members of the House GOP conference made him well-positioned to broker a compromise. In May and early June, Diaz-Balart spent his evenings quietly shopping a PowerPoint presentation of a border enforcement and legalization bill to his colleagues. He poll-tested the proposal. He recruited a whip team of roughly eight lawmakers and they secured soft commitments from at least 120 Republicans, enough to pass Democratic support, according to multiple sources familiar with the process.

He had planned to sit down with House leaders on June 12, ask for a week to firm up the numbers and secure their commitment to bring the bill to the floor — from which he hoped it would pass with a bipartisan majority. Behind the scenes, he kept the White House informed of his actions. Obama held out hope that Diaz-Balart might succeed where so many others had failed, agreeing to delay the release of a narrow batch of executive actions on immigration to avoid antagonizing conservatives at a delicate moment in Diaz-Balart’s negotiations.

But then, just two days before the meeting, Eric Cantor, the House majority leader who had gingerly supported certain immigration reforms, lost the Republican primary for his Virginia House seat to an insurgent candidate who hammered him for his supposed softness on immigration. “Eric Cantor saying he opposes amnesty is like Barack Obama saying he opposes Obamacare,” thundered Dave Brat, an obscure college professor who challenged the powerful majority leader. Beating Cantor, Brat claimed, “is the last chance” to prevent undocumented immigrants from pouring into the country.

“We were so close,” Diaz-Balart says now. “We were closer than the House has ever been.”

Democratic misgivings

Obama was back at square one. He had no bill to sign. And he was coming under pressure from his liberal allies. Hispanic advocates remained furious with him for waiting so long to do something— anything. Frustrated Senate Democratic leaders prodded him to take unilateral action by the end of the summer — just before the midterm elections — a timeline that White House officials tried unsuccessfully to get the senators to reconsider.

Then, in a face-to-face meeting outside the Oval Office in late June, House Speaker John Boehner informed Obama that not only would his Republican members decline to address immigration, they planned to sue the president, as well, for exceeding his authority in a variety of administrative actions taken in the absence of congressional approval.

A week later, Obama had settled on his course: He would go it alone, and take much broader executive action than the rest of Washington expected. And he would act soon, setting an end-of-summer deadline. Speaking in the White House Rose Garden, the president turned combative as he repeatedly veered from his prepared remarks.

“The failure of House Republicans to pass a darn bill is bad for our security, bad for our economy, and it’s bad for our future,” he thundered. “Drop the excuses.”

But Obama had bigger problems than Republican intransigence.

A shocking influx of tens of thousands of unaccompanied children, sent by their parents from violence-torn villages in Central America, were crossing the southwestern border of the United States, where overwhelmed federal border guards struggled to find ways to handle them. Some news reports mistakenly suggested that the parents were responding to Obama’s promises of leniency; and as the numbers of children grew, even some previously supportive Democrats began getting cold feet about Obama’s plans to loosen immigration rules at a time when they feared it could send still more migrants flooding to the border. The first signs of the impending border crisis had been visible when Obama made his June announcement, but Democrats did not anticipate how it would alter the political landscape.

National Republicans soon launched a campaign to make the border influx a defining issue in the midterm elections. But Obama, at first, was unmoved.

In July, one White House aide dismissed the notion that Obama would pay much heed to the potential damage to Democratic candidates in conservative areas of the country. “My guess is it is pretty minimal,” the official said when asked what effect the fate of his party in the midterms would have on Obama’s decision. “We are going to do what we think is the right thing to do.”

Testing the legal boundaries

As the politics got worse for endangered Democrats, outraged liberal activists were besieging the White House with demands for what should go into his executive orders.

Senior White House officials including counsel Neil Eggleston and domestic policy adviser Cecilia Munoz hosted more than 20 sessions in July and August with business, labor, Hispanic activists and lawyers. There was no shortage of special pleadings.

The Congressional Hispanic Caucus wanted Obama to protect all 8 million undocumented immigrants who would have been eligible for legal status under the Senate bill. Oracle, Cisco, Microsoft and other high-tech players pressed officials to include some of their longstanding requests, such as recapturing unused green cards to bring in more skilled workers from abroad. So-called “dreamers,” the young undocumented immigrants for whom Obama extended administrative relief in 2012, pleaded for similar leniency for their parents. Undocumented farm workers sought a special carve out, too.

That only added to the pressure on Johnson and his small working group back at the Department of Homeland Security, who were struggling to come up with a plan that was legally defensible and yet sufficient to address the political demand. Some advocates, including California’s liberal Rep. Zoe Lofgren, an immigration attorney, drafted extensive memos for the administration laying out their own legal rationales for expanded executive action.

At DHS, however, Johnson and his team were hungry for information to back up their decisions. As time went on, they leaned more heavily on the work of the Migration Policy Institute, a nonpartisan Washington think tank that churned out data that caught the department’s attention. One report offered detailed projections of how each of the different categories of undocumented populations might benefit from executive action — possibilities based mostly on educated guesses from the Institute’s experts.

DHS aides were impressed enough to seek two personal briefings for Johnson from the Institute’s staff.

The process appeared to be humming along.

A debate on Air Force One

On Labor Day, Obama was traveling to Milwaukee, a battleground in recent years with Republicans as they’ve sought to curb union benefits. The president invited a small group of top labor leaders to fly with him to the event. The conversation aboard Air Force One turned to a heated political debate: whether Obama should take executive action on immigration before the November election.

Mary Kay Henry, president of the Service Employees International Union, urged the president to stick with his plans to act by the official end of summer, less than three weeks away. But Leo Gerard, president of the United Steelworkers, argued that Obama should delay the announcement until after the election, out of concern for Democratic Senate candidates who might be caught in the backlash. The conflicting advice, some advocates contend, undermined the unified front that activists were desperate to maintain, particularly as Senate Democrats grew nervous. (Gerard and Henry declined to comment.)

Over the next few days, more and more Democrats began siding with Gerard.

What really worried the White House was that opposition wasn’t limited to vulnerable moderates up for reelection in Republican-leaning states. Sen. Al Franken, a liberal from Minnesota, expressed concerns. Sen. Bill Nelson (D-Fla.), who wasn’t on the ballot, pointedly asked Obama to wait until after the election. And Sen. Angus King (I-Maine), who caucuses with Democrats, declared openly that it would be a “mistake” for the president to do anything alone, ever.

When King personally delivered that message to White House chief of staff Denis McDonough, the Obama team knew it had a problem. If an independent from Maine, a state Obama won by 15 points, couldn’t support the president’s actions on immigration, they really were in trouble. David Simas, the White House political director, asked Guy Cecil, the executive director of the Democratic Senatorial Campaign Committee, for polling on the immigration issue. Cecil gave him polls commissioned by the Iowa and Arkansas Senate campaigns, showing vast numbers of voters who didn’t want Obama to ease pressure on undocumented immigrants without the agreement of Congress.

The White House realized it couldn’t put out an executive order that would get attacked by candidates of the president’s own party. By that Friday night, as Obama flew home from a NATO Summit in Wales, he began calling allies to inform them of his decision to delay action — dealing yet another setback to the immigration reform advocates and the president’s relationship with Hispanic voters.

The anger was palpable as the Congressional Hispanic Caucus squared off with top White House officials in a meeting room steps away from the House floor in September, days after the announcement. The lawmakers viewed the president’s decision to delay action as the latest in a long line of broken promises.

As they sat around a long table in a meeting room of House Minority Leader Nancy Pelosi’s office, more than a half-dozen lawmakers spoke as the caucusgrew impatient with McDonough, Munoz, and other Obama aides.

Democratic Reps. Tony Cardenas and Rep. Lucille Roybal-Allard spoke about the pressures they were under from impatient and disappointed constituents in Los Angeles. Cardenas, in particular, pressed the White House to maximize the number of undocumented immigrants who could be protected under the president’s authority — telling officials that if the number of immigrants covered under Obama’s order turned out to be smaller than expected — say, 3.5 million — he would feel that Obama hadn’t gone far enough.

Rep. Luis Gutierrez (D-Ill.), for his part, was adamant that the Obama administration follow through on executive action by Thanksgiving.

Roybal-Allard wanted to know: Would the formal recommendations from the caucus, which lawmakers had sent months earlier, be included?

They had the memos, the aides responded.

The lawmakers, White House aides promised reassuringly, would be pleasantly surprised by the outcome.

Closed doors at DHS

The drafting process going on in the bowels of the DHS headquarters was a mystery to those on the outside. And that’s the way Johnson — and the White House — wanted it.

Disciplined and direct, Johnson approached his work for the White House like an attorney going to the mat for his clients. Unlike some political figures, he wasn’t interested in buffing up his own image. As an early supporter of Obama’s 2008 campaign, Johnson had credibility in the president’s insular world. No matter what, he wasn’t going to leak details of the president’s plan.

WATCH: President Barack Obama's "one step forward, two steps back" history on immigration reform.

Despite his scant knowledge of the complex web of immigration laws when Obama first handed him the assignment, he took personal ownership of preparing the president’s policy. He held dozens of meetings with outside legal experts, lawmakers and interest groups, including NumbersUSA and Center for Immigration Studies, fierce opponents of legalizing undocumented immigrants.

But rarely did they walk away with any sense of Johnson’s thinking.

“He’d be a terrible person to play poker [with]. He could have a cheap-ass hand and you’d think he’d have four aces,” Gutierrez said. “He almost stops breathing when you ask him a question. I feel he gets like, catatonic, like ‘I ain’t telling you nothing. I’m not going to give you any verbal, non-verbal indications of affirmation. I’m not going to let you read me.’”

Johnson’s circle of aides included Capitol Hill veterans like Esther Olavarria, who worked for the late Sen. Ted Kennedy (D-Mass.), a leading champion on immigration reform for decades; David Shahoulian, a former Lofgren aide; and Serena Hoy, who worked on immigration issues for Sen. Harry Reid (D-Nev.). Their former colleagues on the Hill struggled to get anything out of them, too.

“These are people that are not going to overstep,” said a prominent immigration attorney who has known the key players for years.

By one count, Barack Obama, Jeh Johnson and their staff produced more than 60 iterations of the executive order proposal. | Photo by Pete Souza

Obama and Johnson, as well as their staffs, traded draft memos and ideas for months. By one count, they produced more than 60 iterations of the proposals. Johnson’s aides would draft something, then shoot it over to Eggleston and Munoz to examine and return with revisions.

The deliberations had gone on for almost eight months without any major leaks on the policy proposals — a feat that impressed White House aides.

But once Johnson’s tight circle expanded last week, the broad outlines of the plan began to seep out, starting the clock on the White House’s rush to unveil the most sweeping executive action on immigration in history.

“He ran an airtight process,” a senior White House official said of Johnson. “It was an impressive thing.”

Shifting into sales mode

As soon as Republicans realized the president was preparing to act, in the days after the GOP’s big victory in the midterm elections, they took to the airwaves to decry his abuse of authority. He was a king, an emperor, a heavy-handed executive abusing his power. Democrats, for their part, didn’t know enough about the president’s plans to offer any defense.

By this week, a belated White House response team kicked into high gear. Munoz and senior adviser Valerie Jarrett, the president’s closest aide and confidante, quickly ramped up their outreach. They put out calls to high-tech companies, detailing several changes that would make it easier for them to retain foreign workers. They summoned civil rights leaders in an effort to get buy in and work the grassroots. They dropped hints to Hispanic activists that they would be happy with the result.

But even in the lead-up to Thursday’s prime-time address, not all the president’s allies were happy.

The AFL-CIO, for one, was continuing to voice its displeasure over what it was hearing, including a sweetener for the tech industry that was reportedly included. Top union officials reached out to the Congressional Black Caucus to press their case that a provision to allow tech companies to recapture unused visas would harm American workers.

The White House realized it couldn’t put out an executive order that would get attacked by candidates of the president’s own party. | AP Photo

By Wednesday night, the months of political acrimony, second guessing, and behind-the-scenes furor appeared to subside as Obama sat down for dinner with 18 congressional Democrats. Placed next to the menu of crisp fennel cucumber and tomatoes salad, thyme-roasted rib eye and artichoke puree, was a card with talking points on immigration.

If critics raise the amnesty charge, the response should be: “Taxes and background checks aren’t amnesty. That’s accountability. Doing nothing — that’s amnesty.”

If the president’s legal authority is questioned, say: “Every president for 70 years, both Democrats and Republicans, has taken executive action on immigration.”

When Republicans argue for a government shutdown over it, supporters should respond: “Republicans are blocking funding to conduct millions of background checks.”

As the group sipped on a Cabernet Sauvignon from Washington state and a California Chardonnay in a White House dining room, Obama gave his pitch. His legal rationale was sound, his politics solid. House Republicans had plenty of time to take up immigration reform. More than 500 days had passed since the Senate approved its own comprehensive reform bill, Obama noted.

“This is bold,” Gutierrez told the president. “This is courageous, and generous.”

This one critic at least had finally been converted.