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.”

Even as the 2016 campaign begins to get going, no top contender yet has laid the groundwork for a national fundraising network necessary to stay competitive in a long primary season. In New York, there remains a definite desire for Chris Christie to regain his footing after the controversy surrounding the closure of the Port Authority, or, failing that, for Paul Ryan or Jeb Bush to jump into the race.

“Jeb is like an old-pair of shoes—you know exactly what they are going to feel like when you put them on,” said one fundraising vet. “In many ways, he is the most logical. He is ready to go.”

One of the unique aspects of a potential Paul candidacy, however, is that unlike Romney, he actually doesn’t need to rely on New York money. When he ran, Ron Paul raised over $50 million, mostly from a grassroots army of true believers. And supporters of Rand Paul think those donors will be there for him too.

“You take the 50 million his dad raised, and what do they need, another 25 million?” said one person close to the senator. “He gets that, he is very real, and very substantial.”

Ties to the army of Paulites can cut both ways however. Congressman Paul was certainly never a welcome figure in Fifth Avenue penthouses, and to some, Rand bears too much resemblance to Ron. And even though supporters of Paul say that he can pivot away from his father while still keeping the core group of supporters—a move similar to one George W. Bush pulled off as doubts lingered about his resemblance to his father, it may not be enough for those who had to cross a barricade of Paul picketers to get to the VIP suite at the last GOP convention.

“I don’t think the people who were for Romney, McCain and Bush will be for him,” said one donor to all three candidates. “But unlike his father, they do not think he is crazy.”

And it is not just his ties to his father that’s giving some potential donors pause. It is also his tendency to occasionally veer off-script, as he did recently with his attacks on Bill Clinton and Monica Lewinsky.

“With Chris Christie, they know what they are getting,” said one person who has met privately with Paul. “With Rand, are you getting the articulate spokesman for the issues or the guys who goes after Bill Clinton when he should be attacking Hillary.”

But if Paul cannot make inroads in New York, his supporters say that there are rooms he can go to that other GOP candidates cannot. Next week, for example, he is heading out to Silicon Valley, where his libertarian-leaning politics are likely to get a better hearing, and where one well-heeled supporter can bankroll an entire campaign.

“Look at guys like Peter Thiel and Marc Andreessen,” said one Paul supporter, referring to the two mega-wealthy libertarian Silicon Valley figures. “They have billions and billions of dollars sitting on the sidelines, waiting to be invested in the right project, and people like that are very excited about Rand.”

For now, nearly every member of the donor class of New York and other wealthy enclaves insisted that the fundraising race was in a holding pattern, as Republicans waited on Christie and Bush, even though Paul supporters have been talking up his strong early polling numbers in an effort to lock-up fundraising commitments.

“People in the Republican Party this year more than anything just want to win,” said one hedge-fund manager and major donor to the cause. “Contributions are going to be a lot less about ideology, and a lot more about practicality.”