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The Fast Rise And Fall Of Jesse Benton, Rand Paul's Most Loyal Lieutenant

Benton went from young organizer to Paul family member and presidential campaign manager in a matter of years. After his indictment on Wednesday, people in and around Rand Paul's campaign say the campaign is a mess.

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The federal charges announced Wednesday against Jesse Benton mark a jarring, high-profile flameout for the long-serving Rand Paul adviser and top-flight Republican operative who was hailed until recently as a rising star in the party — a grim political trajectory that many in Paul's orbit now tell BuzzFeed News their candidate seems doomed to follow.

In interviews Wednesday with more than half a dozen people close to Paul — including current staffers, top fundraisers, and key allies — Benton's indictment was cited as evidence of deeply rooted problems in Rand Paul's campaign, from organizational dysfunction, to personal failures of judgment by the candidate himself.

Benton, who runs the pro-Paul super PAC, was indicted on Wednesday for concealing payments to an Iowa state senator in exchange for the senator's endorsing Ron Paul in 2012.

One of Paul's aides called the situation "a total mess" and added, "I don't think there's any coming back from this." A fundraiser and personal friend of the candidate, meanwhile, said the Benton episode has convinced him that Paul is "not running a campaign worthy of the presidency of the United States." Another friend and informal adviser said of the candidate's presidential bid, "It's over." (All the sources quoted here requested anonymity to speak candidly without risk of losing their jobs, or their personal relationships with Paul. Benton did not respond to an interview request.)

The indictment against Benton is not the first speed bump the candidate has hit on his road to the White House this year. The myriad problems plaguing Paul's presidential campaign have been extensively chronicled in recent news reports, which detail the libertarian's long way down from GOP "it" boy of 2013 to flailing also-ran of 2015.

In response to this latest crisis, a spokesman for Paul released a statement Wednesday afternoon suggesting the Justice Department was "politically motivated," and stating, "These actions are from 2012 and have nothing to do with our campaign."

But inside Paul's already fractious campaign, the news has set off a flurry of finger-pointing and recriminations. In the immediate wake of the indictments, several sources who spoke to BuzzFeed News tried to pin the blame for the fiasco and its fallout on various rivals within the organization — passing along unconfirmable accusations and unprintable rumors about each other on a not-for-attribution basis. One question came up repeatedly: Why was Benton entrusted with such a vital position — to raise the big-dollar donations at the super PAC — when he was still being investigated by the FBI, and at serious risk of an indictment?

The answer stems from Benton's own unique ascent within the first family of American libertarianism — and those closest to Paul say it's emblematic of the broader problems posed by the candidate's complicated personal and political entanglements with the movement.

Benton first met Rand's father, Texas Rep. Ron Paul, in 2007 while working with a libertarian political consultant whose modest office sat in the back of a Korean deli in northern Virginia. Drawn to Paul's dovish foreign policy views and fiscal conservatism, Benton began volunteering for the candidate's long-shot presidential campaign and was eventually added to the payroll. At the same time, he fell in love with Paul's granddaughter, Valori, and a year later they got married.

From there, Benton embedded himself in the national liberty movement as a professional super-activist, and in the Paul family as a preternaturally attentive in-law. When Rand decided to launch an insurgent U.S. Senate bid during the 2010 race in Kentucky, Benton moved into the candidate's basement and spent every waking hour either working for the campaign or taking part in family dinner and game nights. The living situation wasn't ideal. Rand and his family were lean-framed health nuts who kept the temperature in the house high, and ate austerely portioned meals; Benton was stocky and sweaty and, as he would later tell colleagues, perpetually hungry throughout his stay.

Still, the comfort level he achieved with the family came in handy during the campaign. Benton was, for instance, one of very few people on Rand's staff willing to tell him that the necktie with the large, open-mouthed fish pattern was not very senatorial and that he should probably stop wearing it in public. More substantively, when Rand became consumed with an Ahabian quest to explain to the national news media — in one painful TV hit after another — the logic of his objection to a certain section of the Civil Rights Act, Benton relied on his knowledge of the Paul family dynamics. He encouraged Rand's wife, Kelley, to intervene, knowing she was the only one who could get through to him. (She did.)

When Rand ultimately won the Senate race, Benton — whose talent for grassroots political warfare had mobilized an army of libertarian activists and tea partyers — became the natural choice to head Ron's 2012 presidential campaign. And when that campaign unexpectedly caught fire, defying the expectations of 2012 observers, Benton was catapulted into the lucrative realm of A-list political consulting.

Those around him said Benton seemed to relish his new status. He bought a million-dollar house in Louisville, Kentucky. He slimmed down considerably, and swapped his baggy suits for a newly stylish wardrobe. He cultivated relationships with influential journalists, and won many of them over with his easygoing accessibility and authentic earnestness — traits rooted in the idealism of the protest campaigns he often worked on (and not commonly found among the more cynical political mercenaries in his industry).

Benton's peak came when then-Senate Minority Leader Mitch McConnell — one of the most powerful Republicans in Washington, and someone who could have had his pick of campaign managers in 2014 — tapped him to run his re-election bid in Kentucky. Suddenly, Benton was being profiled in National Review, and musing about how, "Once we win this campaign, there's going to be a substantial portion of Team Mitch that's going to fuse with Team Rand… it's going to make a really dynamite team."

At the same time, Benton was privately boasting that prospective 2016 presidential campaigns were knocking down his door. He told some colleagues that Sally Bradshaw had tried to recruit him to Jeb Bush's team. He told others that the Rubio camp was talking to him. (Officials at both campaigns declined to comment when BuzzFeed News asked for confirmation, both saying they didn't want to publicly discuss internal staffing decisions.)

While Rand was enjoying his moment as the darling of the national media — "the most interesting man in politics," as one Time magazine cover famously declared him — Benton seemed to be enjoying his own moment in the spotlight.

"I don't know what I'll do in 2016," one Paul aide recalled Benton cavalierly telling him at the time. "I'll work for [Rand] — if he can come up to my price."

Looking back on it now, several of Benton's colleagues in Rand's orbit said the bravado was likely an act of misdirection. Unbeknownst to outsiders, investigators were looking into whether Ron Paul's 2012 presidential campaign had illegally paid tens of thousands of dollars to Iowa state Sen. Kent Sorenson to get him to retract his endorsement of Michele Bachmann during the primaries, and give it to their candidate instead.

Two sources in Rand's inner circle said the senator himself was worried the investigation might soon reach Benton, and consequently hesitated to promise him a perch in his likely presidential campaign. One source speculated that Benton was upset by the perceived disrespect, and that all his bragging about other job prospects was a form of venting. Another source interpreted it as Benton's way of keeping his market value high while he angled for a backup job.

In any case, Benton kept up the outward displays of confidence in August 2014, when Sorenson pleaded guilty on two federal charges and news of the federal investigation became public. Benton was forced to resign as McConnell's campaign manager. According to of Benton's colleagues, immediately after his departure from the campaign, the strategist bought a new Audi, and a gold Rolex for his wife.

One of the colleagues was concerned by the the extravagance, and urged prudence. "Dude, you don't know where your next paycheck is coming from," he recalled telling Benton. "This is not the time to splurge."

By now, it was early in the fall of 2014, and Rand Paul was still widely considered a top-tier presidential prospect. But the investigation prompted some of the senator's more experienced, establishment-friendly allies to worry that other ticking time bombs might be wedged into his organization. Some encouraged Rand to use the news of the investigation as a catalyst to "audit" his entire team — checking to make sure that none of his aides were harboring secrets that might disrupt his 2016 campaign if they became public.

"If nothing else, I thought it would demonstrate leadership at the time of a crisis," said one of the advisers who advocated for this plan. "Particularly with people so close to him, if he would be proactive and not just defend Jesse it would show that he's leading. I thought it was a real opportunity."

Rand ultimately passed on such advice. He didn't cut professional ties with Benton while the aide was under federal investigation. Earlier this year, the senator installed his niece's husband at the head of his super PAC, tasking him with the high-stakes job of high-dollar fundraising all through 2016. The move was widely viewed by his staff as a compromise meant to shield the campaign from any fallout from the Iowa investigation, while also satisfying family loyalty.

But some of his advisers and allies argue now that while his sense of loyalty is admirable, the risky bet he took on Benton was reckless. "Rand obviously feels great loyalty to Jesse," said an adviser. "He helped him get elected in 2010. He's family. Would I have done the same thing? No, I wouldn't have."

For now, Benton's future in Paul's 2016 organization is uncertain — but he may very well have a second act in him. One senior official at a rival presidential campaign told BuzzFeed News Benton was "an extremely talented operative" who would "absolutely bounce back." In fact, the official said, he would gladly hire him — "once this indictment stuff blows over."

McKay Coppins is a senior writer for the BuzzFeed News politics team, and the author of The Wilderness, about the battle over the future of the Republican Party.

Contact McKay Coppins at mckay@buzzfeed.com.

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