Among those involved the 2016 money sweepstakes, theories of Paul’s struggles abound. Some point to his anti-establishment posture, which has alienated some in the business community — much of whose support has gone for Bush. Others say his more dovish foreign policy stances has turned off Jewish Republicans, many of whom view him as insufficiently pro-Israel. Still others say he’s found competition from Cruz, who like Paul has branded himself as a free-market thinker. Others contend that Paul’s unpolished style might be working against him as he seeks out the support of wealthy Republican benefactors, While attending a California donor conference sponsored by Charles and David Koch, two of the nation’s most powerful Republican donors, Paul was criticized for dressing casually in jeans, slouching in his chair and giving rambling answers to questions. One person briefed on the Kochs’ thinking said Paul’s star has faded in their eyes, and that it’s now hard to see them providing substantial financial support to the Kentucky senator.
At times, he’s seemed to be more on defense than offense. Earlier this year, Paul had a private meeting with casino mogul Sheldon Adelson, who’s given millions of dollars to pro-Israel causes. During the meeting, Adelson provided the Kentucky senator with assurances he wouldn’t spend money explicitly to defeat him. To some, it’s not entirely surprising he’s struggling to win over the party’s donor elite. In 2010, when he upset the political world by defeating Senate Republican Leader Mitch McConnell’s handpicked candidate in the Kentucky Senate primary, Paul’s deepest well of support came from his party’s activist set. It’s those conservative activists, many believe, whom Paul must win over in 2016. “The worst thing for a presidential candidate to be is something it’s not,” said Nick Everhart, a former Paul adviser who worked on his 2010 campaign. “If small donors are his place in the field, that’s got to be where he is.”
Still, at times the rejection has stung, especially when he’s tried to win over his home state’s moneyed class. A few months ago, Paul invited Joe Craft, a Kentucky coal company executive and his fiancée, Kelly Knight, to have breakfast in the Senate dining room. But the couple, who rank among the most prominent Republican givers in the state, had bad news for Paul: They wouldn’t be getting behind his presidential bid. In a brief interview, though, Knight recalled giving Paul a consolation prize of sorts. The Crafts would, she told him, “strongly support him in his Senate reelection campaign.”