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In December 2012, four Democratic and four Republicans senators, known as the Gang of Eight, began drafting a comprehensive immigration reform bill that would provide a pathway to citizenship for the more than 11 million undocumented immigrants living in the United States. One of the first and most important negotiations was over who would qualify for that pathway. Would all undocumented immigrants be eligible, or would some be left in the shadows?

Democrats sought to grant them all access to the long road to citizenship. Sen. Marco Rubio, the most conservative Republican in the group, wanted to require undocumented immigrants to have lived in the country for five years in order to be eligible. And so the negotiations began.

Rubio’s presence in the gang was crucial to passing reform. Elected in 2010 on the tea party wave, the senator from Florida had credibility among conservatives; the other seven members hoped he would provide cover to other Republicans to support the legislation. Rubio, in turn, needed a bill that was conservative enough to sell to his fellow Republicans.

Rubio had plenty of leverage. If he walked away at any point, the bill would be doomed. But Rubio and his staff also had to gauge what would be acceptable to the right, so that he wasn’t left twisting in the wind when the bill was put to a vote. The other Gang of Eight senators—Republicans John McCain and Jeff Flake of Arizona and Lindsey Graham of South Carolina, and Democrats Dick Durbin of Illinois, Chuck Schumer of New York, Michael Bennet of Colorado, and Robert Menendez of New Jersey—and their aides worked hard to make the bill’s provisions palatable to conservatives, even if the changes were largely cosmetic. “He was basically the backstop, [the] vetoer,” one Democratic aide recalls. “Nothing could get done without his approval.”

But when it came to who was eligible for that path to citizenship, both sides initially dug in, according to several Democratic aides who were present at the negotiations. Then Rubio blinked, agreeing to a compromise closer to the Democrats’ proposal. And he made an additional and unexpected concession: The bill would allow immigrants who had already been deported to return to the United States and get on the road to citizenship.

Rubio “gave up a lot, probably for something he should have still held firm,” says one aide. “And it’s not clear if that was because he was a bad negotiator or he had a good heart.”

“He was basically the backstop, [the] vetoer,” one Democratic aide recalls. “Nothing could get done without his approval.”

For Rubio, now a leading contender for the Republican presidential nomination, his work on the immigration bill—perhaps the most notable effort of his short Senate career—remains a matter that could blow up his candidacy, even though the bill never became the law. (In June 2013, it passed in the Senate with a bipartisan majority, but then-Speaker John Boehner, yielding to right-wing opposition to the measure, would not bring it to a vote in the House.) To conservative Republicans who favor a tough approach to illegal immigration, Rubio’s participation in the Gang of Eight is disqualifying. To moderate GOPers, who see the need for their party to expand its appeal among Latinos, a fast-growing and critical voting bloc, Rubio’s work on the bill is a selling point for the general election. Rubio’s challenge has been to try to win over both sides, a difficult task given that conservatives find him too liberal on immigration and reform advocates view Rubio’s subsequent attempt to distance himself from the Gang of Eight bill as a betrayal.

On the issue of eligibility for the path to citizenship, Democrats wanted all undocumented immigrants to qualify, no matter when they had arrived in the United States. Why leave some immigrants behind, they argued, and let them become a future problem? But Rubio, in private talks, initially called for the five-year requirement. He pointed out that the Dream Act—a 2011 bill, authored by Durbin, which would have allowed undocumented immigrants who grew up in the United States to gain legal status—included a five-year requirement, one aide remembers. And when President Barack Obama announced an executive action in June 2012 to allow young, undocumented immigrants, known as Dreamers, to stay in the country, he also used the five-year standard. (In 2014, when Obama would announce a second executive action to expand the number of undocumented immigrants who could avoid deportation, it likewise had a five-year mandate. That initiative is currently tied up in the courts due to Republican opposition.)

As one Democratic aide put it, Rubio had a “good argument,” which could have ultimately carried the day, given his leverage in the group. But in the course of the negotiations, Rubio gave up on the five-year requirement.

Rubio “gave up a lot, probably for something he should have still held firm,” says one aide. “And it’s not clear if that was because he was a bad negotiator or he had a good heart.”

He and the other senators agreed that undocumented immigrants needed to have been present in the United States by December 31, 2011, to be eligible—just 1.5 years before the bill would be approved by the Senate. So the Democrats fared better in this compromise than did Rubio. But then the Democrats got an even better bargain. In return for the December 2011 deadline, Rubio and his GOP colleagues agreed to allow some undocumented immigrants who would have been eligible to apply but had been already deported to re-enter the country and begin the citizenship process.

“We were shocked, frankly, that they—the Republicans—were willing to accept that provision,” another aide recalls. Under Obama, the pace of deportations had accelerated. By the end of 2012, his administration had deported about 1.6 million undocumented immigrants, separating families and threatening Democrats’ standing among Latino voters. The prospect of reuniting some of those families made the provision an important victory for the Democrats in the gang. By the end of the negotiations, it became clear to Democrats that Rubio had never been a hardliner when it came to the pathway to citizenship—his concern was more with how it looked to other conservatives.

The Rubio campaign did not respond to a request for comment.

The son of Cuban immigrants, Rubio had long danced back and forth on the immigration issue. In the Florida state House, Rubio used his position as House speaker to keep anti-illegal immigration bills from getting a vote, and he supported tuition assistance for the children of undocumented immigrants. But when he rode the conservative tide in 2010 to win his Senate seat, Rubio used phrases like “illegal aliens,” bashed “amnesty,” and opposed the Dream Act. Once in the Senate, however, Rubio began to position himself as a leader on immigration reform by working on a what was referred to as a “Republican Dream Act,” only to scuttle the effort after Obama announced similar measures through his June 2012 executive action for Dreamers.

Rubio’s Dream Act, though, did signal to Democrats that he was willing to go out on a limb on immigration. So in December 2012, after Obama won re-election with 73 percent of the Latino vote, Durbin approached Rubio during an early-morning workout in the Senate gym to ask him about joining the gang. After receiving assurances that the bill would address border security as well as a pathway to citizenship, Rubio was in.

Rubio’s decision to join the gang was a political gamble, but one that seemed worth taking. At the time, the Republican establishment was calling for the party to mend its relationship with Latinos. In March 2013, the Republican National Committee urged the party to “embrace and champion comprehensive immigration reform” or “our Party’s appeal will continue to shrink to its core constituencies only.” If Rubio could help his party turn a corner with Latinos, it would not only be a big policy win under his belt, but make him a central figure in the party—perhaps even a presidential contender. A Time magazine cover dubbed him “The Republican Savior.”

Once he joined the Gang of Eight, Rubio was a key player, involved in every aspect of the negotiations. When it came to undocumented immigrants, he was “all in” on the path to citizenship, as one staffer put it. In dozens of meetings between the eight members over six months, Rubio never “took anything approaching a hardline on the path to citizenship,” says the aide. “It was always, for him, about ‘how do I sell this?’…It was much more about the marketing perspective, and he was very open in saying that.”

Even as Rubio struggles to stay on both sides of the issue, his role on the Gang of Eight is coming back to haunt him.

Rubio was insistent that it not appear that undocumented immigrants were receiving special treatment. So the pathway to citizenship—which the bill ultimately laid out as a 13-year process from receiving legal status to obtaining a green card to applying for citizenship—was tailored so that it was also open to people who immigrated legally and applied for visas through other channels. Whether the undocumented got their own visas or visas also available to other immigrants would yield the same outcome, but this allowed Rubio to claim that no special treatment was being granted.

Rubio took his task of selling the bill to his fellow conservatives seriously. He went head to head with talk radio personalities, including Laura Ingraham and Mark Levin. One Sunday in April 2013, he went on all five Sunday talk shows plus Univision and Telemundo to promote the bill. Politico called it the “Full Marco.”

But it didn’t work. The conservative media never bought in, and neither did their viewers. To get the bill over the finish line, the gang turned to two other Republican senators, Bob Corker of Tennessee and John Hoeven of North Dakota, to pass the Corker-Hoeven amendment to beef up border security provisions. When the bill reached the Senate floor, Rubio gave a moving speech in its favor. But after it passed on a 68-to-32 vote and the gang gathered for a celebratory press conference, Rubio didn’t show up.

The reform effort subsequently died in the House of Representatives. Though some Democrats faulted Rubio for not lobbying House members to take up the bill, others believe that his political capital had run out.

What irked immigration reform advocates was that Rubio not only stopped advocating his own bill; he stopped supporting it. First, he signaled that the House should not take up the bill, saying that other matters, like repealing Obamacare, were a higher priority. Since then, he has said that though he still supports reform, the comprehensive approach he backed with the Gang of Eight was the wrong approach. Recently, he has distanced himself from important provisions of the bill, such as a measure that would allow undocumented immigrants to successfully apply for green cards after 10 years. He also said he would allow Obama’s executive action for young immigrants to expire, resulting in the deportation of Dreamers.

Instead of a comprehensive bill, Rubio now prefers a piecemeal approach to immigration reform. First, he wants to address border security with more guards along the border, fencing, and a tracking system to find people who have overstayed their visas. Next, he wants to modernize the immigration system, moving toward a merit-based system for visas. Only after all that does he want to deal with the 11 million undocumented immigrants.

Rubio still says he backs a pathway to citizenship for the undocumented along the lines of what his Senate bill spelled out—from legal status to green cards to eligibility for citizenship—but that claim is hard to square with his reversals on key provisions of his own bill. The ambiguity of his position is evidence of the political tightrope he is walking. It allows him to talk up border security in the Republican primary and preserve an opening to stress his support for a pathway should he reach the general election. But reform advocates accuse him of empty rhetoric, given that meaningful immigration reform is likely politically impossible unless packaged with border security measures. “The reason that makes us so furious is that he knows that approach would never pass the Congress,” says Frank Sharry, who runs the pro-reform group America’s Voice.

Even as Rubio struggles to stay on both sides of the issue, his role on the Gang of Eight is coming back to haunt him. Conservatives have attacked him for supporting what they call “amnesty.” One group is relentlessly using the immigration bill to tear down Rubio and promote its preferred candidate, Sen. Ted Cruz of Texas. Details of the Gang of Eight negotiations, demonstrating Rubio’s openness to a pathway to citizenship, will do nothing to help him among this constituency. Meanwhile, his abandonment of the effort has raised serious questions about his ability to appeal to Latinos in a general election. It’s a delicate balancing act, and he’s getting pushed from both sides.