Sen. Rand Paul (R-Ky.) is already trying to woo establishment Republicans and big donors. There is no secret why: His band of loyal libertarians is insufficient to deliver the nomination. Most especially in big states, there aren’t enough of them to allow him to win enough of the electorate to defeat candidates with wider appeal.

PINEVILLE, KY- MAY 7: Speaking to miners and company owners, Dr. Rand Paul waits to be toured around a coal company mine May 7 in Pineville, Kentucky. Eye surgeon Dr. Rand Paul Ñ Tea Party favorite Ñ is running for the Republican U.S. Senate seat of retiring U.S. Sen. Jim Bunning. The primary is May 18th. (Photo by Melina Mara/The Washington Post) StaffPhoto imported to Merlin on Tue May 11 16:25:10 2010 Rand Paul (Melina Mara/The Washington Post)

If he wants to rise about the ceiling in support his father, Ron Paul, hit he’ll have to win over a lot of evangelicals, business Republicans, hawks and moderates. The task is daunting because each of those groups will have candidates with whom they feel more at ease. Evangelicals can look to Rick Santorum, Mike Huckabee, Sen. Ted Cruz (R-Tex.), Texas Gov. Rick Perry or Indiana Gov. Mike Pence, all of whom have cultivated good ties and are reliable advocates for the foreign policy and social issues they hold dear. Business Republicans will have choices that may include  a slew of governors, as well as Rep. Paul Ryan (R-Wis.). Many of these Republicans, most especially the donors with deep pockets will ask themselves: Why do I need Paul when I can get Gov. X or Sen. Y?

To get past the first round of drinks at the donor cocktail parties, Paul is going to have to deal with very substantial concerns. When I speak to party operatives, big donors, officials at establishment PAC’s and elected leaders and their staff, a number of issues come up again and again:

Reliability: Paul said the shutdown wasn’t a good idea yet wound up supporting it. He told Silicon Valley execs he was pro-immigration reform, but voted against the Senate bill. The sense that he is too beholden to his core supporters to offer them anything but lip service will be a major concern for party insiders. When has he carried through on promises made to those beyond his core libertarian fans?

Uncertainty: In the last week jarring and embarrassing video of Paul’s comments on WWII, his conspiracy theory about Vice President Dick Cheney and the Iraq War and his emphatic repudiation of the military option for Iran have come out. In an interview that just aired on ABC he blithely repeated his view that we should not rule out containment of Iran — a position entirely at odds with every GOP elected leader and 2016 contender — and  the vast majority of Republican voters. What else is out there that would blow up in his face and give either GOP opponents or the Democratic nominee the opportunity to destroy him? Fear of the unknown is going to paralyze a number of big-dollar donors.

Experience: Like President Obama, Paul has nothing to suggest he has executive skills. Running a medical practice and a Senate office isn’t exactly evidence he can direct the federal government any better than Obama has. Indeed, an ideologue with no executive experience is precisely what these donors have suffered through with the current Oval Office occupant.

Character: Paul has been through a number of mini-flaps including questions about plagiarism and promoting himself as a “board certified” ophthalmologist that may give very cautious insiders pause. Paul’s disdain for government can be seen as refusal to play by the rules that everyone else must abide by.

Judgment: Hiring someone like the “Southern Avenger,” refusing to promptly dump him and then becoming testy with the media will make insiders wonder if Paul has a tin ear. If he can’t spot trouble or hire staff who will not embarrass him, how’s he going to get through an election? (Why in the world did he, for example bring on the co-founder of the unilateral nuke disarmament Global Zero plan when one of his big problems is lack of credibility on foreign policy?)

Extremism: If Paul is seeking to disband the Food and Drug Administration, repeal federal labor laws and eliminate (rather than reform) entitlement programs, party regulars will want no part of him. In other words, how libertarian is he? If he really wants to get rid of drones, the NSA, close Gitmo and contain a nuclear-armed Iran, these GOP players will recoil. They’ve yet to see a substantive, reasonable agenda on a host of bread and butter issues, and until they do, many will assume the apple doesn’t fall far from the Paul family tree.

Rand Paul’s task is made all the more difficult because his core supporters are true believers, hard-bitten libertarians who may regard modulation as betrayal. Compromise is not something normally associated with the crowd who backed his father. And candidly, Paul has never been tested. He is, after all a freshman senator, with no legislative accomplishment who got through  a single election in a deep red state. Up against a bevy of impressive and well-funded opponents it’s not clear how he’ll perform.

In short, some party insiders and donors may willing to meet with him, but most very likely won’t be rushing to support him anytime soon.