Marco Rubio went to virtually unprecedented lengths to sell an unlikely crowd on his version of immigration reform. Rubio, the U.S. senator from Florida who announced on Monday that he will run for president in 2016, did Rush Limbaugh. He did Sean Hannity. He checked all the conservative boxes.

"What you are doing is admirable and noteworthy," Limbaugh told Rubio in January 2013, when he was part of the Senate “gang of eight” that released a bipartisan, comprehensive plan to overhaul the nation’s immigration system. "You are recognizing reality."

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In the end, Rubio didn’t end up convincing himself. Three months later, when he appeared on Limbaugh’s radio show again, Limbaugh attacked him, accusing him of selling out to Democrats and “committing suicide” on behalf of the Republican Party.

Two years later, Rubio rarely talks about immigration reform anymore. He backed away from his own immigration bill and now fully admits that immigration reform in a comprehensive, one-fell-swoop sense is not possible. He took that tone when speaking at a conservative conference in February.

“What I’ve learned is you can’t even have a conversation about that until people believe and know—not just believe, but it’s proven to them—that future illegal immigration will be controlled,” he said in a question-and-answer session with Hannity. “That is the single biggest lesson of the last two years.”

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Rubio’s continued dance with immigration reform will be a key issue through which he’ll have to navigate during what he hopes is an 18.5-month run to the White House as the nation’s first Cuban-American president. The 43-year-old Rubio’s argument is that he is conservative but also electable, and can appeal to constituencies that don’t normally vote Republican — namely Latinos and young people.

“He's not an Ivy Leaguer, but the establishment respects him. He's not an ideologue, but the far right of the party doesn't dismiss him,” said Weston Wamp, a former congressional candidate from Tennessee who supports a path to citizenship for undocumented immigrants.

“All things considered, he's our most polished choice. As the youngest candidate in the field, [he will] have an opportunity to bring millennials to his cause. His empathy for immigrants, however, makes him the best hope for the Republican Party to remain relevant with an enormous demographic shift underway.”

But polling shows that Rubio’s immigration shifts could prove costly with those changing demographics. The polling firm Latino Decisions has measured Latinos’ sentiment toward Rubio over the past two-plus years, and has found that his backtrack on immigration has hurt his standing with those voters.

One example: When Rubio took a “leadership role” on immigration — as he did with the Senate “gang of eight” bill — 54 percent of Latinos surveyed said they would be likely to vote for him. After he stepped back from his own bill and said the focus should be placed more on border security, just 29 percent of Latinos said they’d be likely to vote for him. The amount who said it’d be “very unlikely” they would vote for him in the next election doubled, from 25 percent to 51 percent.

“We find no evidence that Rubio’s candidacy will draw significant Latino support for his candidacy or for his party more generally,” wrote Matt Barreto, the co-founder of Latino Decisions.

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His shifts on immigration have contributed to an overall negative impression of him in crucial swing states, according to Latino Decisions. His favorability ratings are underwater in Nevada, North Carolina, Arizona, Colorado, and even his home state of Florida.

It’s also a problem that he does not support President Barack Obama’s recent executive action on immigration, which could potentially shield up to 5 million undocumented immigrants from deportation. 89 percent of Latino voters supported that action, according to Latino Decisions.

That poll and others suggest there is potential upside, however: One-third of Latino voters either haven’t heard of Rubio or haven’t heard enough to form an opinion. But Barreto said getting those undecideds to his side will take a significant amount of outreach.

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Matt Mackowiak, a GOP strategist and the founder of Potomac Strategy Group, suggested that Rubio could get out ahead by unveiling a plan for an immigration overhaul during the Republican primary. It would show he’s serious and shift the conversation away from his past on the issue.

“It will be easier for him to convince Hispanic voters that he’s committed to solving the immigration problem — because he’s already tried it once — than perhaps someone who hasn’t tried at all,” Mackowiak told Fusion.

Mackowiak said he could make a better argument than candidates like Sens. Ted Cruz (R-Texas) and Rand Paul (R-Kentucky), who have been much more steadfast in their opposition to immigration reform.

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Rubio, the son of Cuban immigrants, has a compelling story to tell, starting Monday night at Miami’s historic Freedom Tower. But he has a long hill to climb — Whit Ayres, a GOP pollster who counts Rubio as a client, said recently he believes Republicans will need to pull 40 percent of the Latino vote to win the White House

He and others believe Rubio can be the candidate to do it.

“He's going to have to walk a fine line, but he's capable of pulling it off,” Wamp said. And our party needs him to or we may not have another opportunity to build a bridge to Hispanics for a couple of decades.”

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Brett LoGiurato is the senior national political correspondent at Fusion, where he covers all things 2016. He'll give you everything you need to know about politics, with a healthy side of puns.