He’s won the CPAC straw poll two years in a row. (Very) early primary polls put him leading among likely contenders in New Hampshire, Iowa and Ohio. And pundits are already calling him the 2016 front-runner.

But as the 2016 election season looms, questions remain about whether or not Kentucky Senator Rand Paul can win over one key constituency: those mostly Manhattan moneymen and women who bankroll Republican presidential candidates.

Interviews with over a dozen top GOP donors and people close to Paul say that he has been aggressively courting that crew, making several trips to New York for meetings with would-be presidential campaign contributors.

Compared to previous nominees like Mitt Romney, John McCain, and George Bush, Paul, an ophthalmologist by training, lacks an easy familiarity with, say, the language of private equity or the condition of the slopes at Deer Valley. His backers say that Paul has the potential to rewrite some of the encrusted left-right divide that has gripped presidential contests for generations. His views on criminal justice reform, voting rights, drug laws and the national security state, for example, put him to the left of most national Democrats.

“Everybody agrees that the Republican brand hasn’t been getting the job done,” said one donor close to Paul, who like others interviewed for this article requested anonymity in order to speak freely about a political process that is still far from settled. “He can be a transformative candidate though, the kind who can fix a lot of what is wrong with the party.”

But that doesn’t necessarily play out particularly well at the Hyatt Regency’s breakfast buffet. This is a crowd that cares about the economy and taxes first and foremost, and doesn’t put much stake in many of Paul’s pet projects.

“Israel is frankly going to be one of his challenges,” said one strategist close to several elite Manhattan donors. Paul has made a point of scaling back many of the nation’s commitments abroad, although he has gradually been getting more hawkish in his defense of the Jewish state. And in private rooms, donors say, he has talked about how scaling back aid to other countries in the Middle East would mean that they would be less able to interfere with Israel’s affairs.

But this explanation, like others, takes time. And although members of the money class say that Paul can sound convincing when he rolls out his libertarian-leaning worldview, they wonder if the context of a presidential campaign is the best place for nuance.

“People like him. He speaks his mind in ways other politicians do not,” said one financier who was a major backer of Mitt Romney. “But the question is, does he have the legs to go the distance? If he is the nominee, I will support him no matter what, but right now I can’t say I know him well-enough.”

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