Hillary Clinton’s $2 Billion Money Man

Meet Dennis Cheng, the longtime Clinton aide in charge of raising hundreds of millions for Hillary’s presidential run.

08.06.15 5:01 AM ET

Dennis Cheng, the finance director of Hillary Clinton’s presidential campaign, the man behind what has been predicted to grow to a $2 billion operation, is serious, soft-spoken, unflappable, and fiercely loyal to his boss.

He is never quoted in the press. He doesn’t participate in profiles, won’t be interviewed, and doesn’t head to cable TV to defend Hillary Clinton against the Republican onslaught. In a political-media sphere in which contact with the Clintons can be a golden ticket to every green room of your dreams, Cheng is determined to be unseen and unheard from.

But, if some Republican operatives have their way, he’s about to become the face of Clintonian corruption.

To hear them tell it, Cheng is the Clinton family’s shadowy and silent partner, one who bounces between the various planets in the Clinton universe, tasked with the one job that the Clintons value above all else: gobbling up hordes of cash.

And they plan to make Cheng known to the wider public, hoping that he becomes the face of the interwoven worlds of Hillary Clinton. And if it hurts her fundraising too, well, all the better.

They point to his time as a fundraiser for Clinton’s 2008 presidential bid, his time as deputy chief of protocol in the Clinton State Department, and from there, to the Death Star, otherwise known as the Clinton Foundation.

“Cheng has been at the very heart of the Clinton family money machine for years,” reads the opening graf of a “background report” provided to The Daily Beast that was put together by the Foundation for Accountability and Civic Trust (FACT), a conservative good-government outfit designed as a counterpoint to the left-leaning Citizens for Responsibility and Ethics in Washington (CREW).

“We are interested in the relationship between the Clinton Foundation and the State Department,” said Matthew Whitaker, FACT DC’s executive director. His group has filed freedom of information requests in order to see what Cheng’s role was, if any, in any back-channeling between the two Clinton concerns. “It seems to us that he is the conduit between where official State business interacts with Clinton Foundation business. He is a young guy who has known nothing other than Hillary Clinton and her money.”

“For nearly a decade, Dennis Cheng has been one of the main power players at the heart of the vast Clinton money machine,” said Colin Reed, the executive director of America Rising PAC, a Republican opposition research outfit that has been churning out negative stories on Hillary for several years now.

“He was one of the leaders of the Clinton Foundation apparatus that raised nearly a quarter billion dollars, including money from foreign governments, and remains a key figure of the 2016 operation that’s pledged to raise a record-breaking $2.5 billion.”

The idea of picking out an otherwise anonymous staffer and portraying him as a modern-day Rasputin has a long history in politics. Democrats did it to Karl Rove, Republicans to David Axelrod and Valerie Jarrett. For Clintonites, the coming effort to turn him into a kind of Benghazi in human form is ridiculous, and smacks of the GOP’s knuckle-dragging obsession to turn everything associated with Clinton into somehow being associated with wrong-doing.

“Oh, please,” said John Morgan, a wealthy Florida attorney who recently hosted a fundraiser in his home. “The Clintons would be attacked if they named Mother Theresa their finance chair.”

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Cheng declined to comment for this story. But when this reporter off-handedly mentioned to a source that this story was in the works, it prompted an immediate phone call from a Clinton spokesperson to find out more.

One longtime source, who counts Cheng as a close friend, declined to speak in even the most general terms about him, saying, “I wouldn’t want to do anything to mess up the campaign.” Many of the more than a dozen top donors contacted for this story said much the same thing. “It will be an unnecessary headache if I talk to you,” said one West Coast-based fundraiser for Clinton.

One thing that Cheng’s detractors get right is that he is exceptionally close to Hillary Clinton. And such proximity is necessary considering the gargantuan task ahead of him: helping to raise the campaign’s part in what has been predicted to be a multi-billion dollar operation.

In conversations with a dozen of some of the Clinton operation’s biggest fundraisers, those who have raised a million dollars or more, many repeated the same thing—that when you talk to Dennis Cheng, it is often as close as you get to talking to Hillary Clinton.

“He has just been with her for such a long time,” said one New York Democrat who has raised over $100,000 for the campaign. “Here’s a guy who moved seamlessly with her over to the State Department, who moved seamlessly over to the foundation. People perceive that making Dennis happy is making Hillary happy, and there are only a handful of people in that orbit you can say that about.”

Cheng came into politics after graduating from Swarthmore College, where he founded the school’s mock trial club and sent the team to the national championships, where Cheng “defended” a fictitious crew of rescued Mt. Everest climbers accused of eating one of their own fallen comrades. (They came in 10th place.)

He interned for Clinton’s 2000 Senate run, and, after a stint at the London School of Economics, he worked on Wesley Clark’s and John Kerry’s presidential campaigns, before coming over to Hillary Clinton’s side in the run-up to her 2006 re-election to the Senate.

And by her side he has largely stayed. During the 2008 campaign, he served as New York finance director, and now serves as one of the few veterans of both that doomed effort and the new campaign.

“That was not a highly functioning place to work,” recalled one former Clinton staffer. “He was probably the most functioning guy there. The only one that seemed like he was on top of his shit.”

From there, Cheng went to work under Clinton at the State Department, where, as deputy chief of protocol, his job was largely to make sure that the proper red carpets were rolled out for visiting dignitaries, and that all scheduled events and meetings go off as planned. He then went to the Clinton Foundation, where in four short years he helped raise a quarter of a billion dollars as the organization was ramping up its efforts before the launch of Hillary’s campaign.

“He is someone who knows way too much to remain in the shadows,” said Keith Appell, a Republican public relations guru who worked in 2004 with the Swift Boat Veterans for Truth and whose firm is helping advise the group releasing undercover videos of Planned Parenthood officials discussing the sale of fetal tissue.

Now he wants Congress to bring Cheng up to Capitol Hill to ask him about the overlap of these various Clinton ventures.

“It is not hard to understand. What you have to do is make the connection between the potential sale of influence by Hillary Clinton and her questionable record as Secretary of State as it relates to the safety and security of the United States. You can anticipate one line of attack to be, ‘Mrs. Clinton couldn’t keep four of her closest associates safe in Benghazi, how is she going to keep the rest of the United States safe.’ Oh, and she is in bed with unsavory characters and taking their money. This is not a hard connection to make and Cheng is at the center of it.”

Part of the coming focus on Cheng, Republicans say, is the hope that if they kick up enough dirt it will begin to make donors think twice about giving to Clinton. So far, at least, those hopes have not been realized. The $47 million that the campaign raised in the first quarter was a record for a non-incumbent, and one that was even more impressive considering that they have only been raising money for the primary in order to avoid seeming over-confident.

The key to Clinton’s record-breaking early hauls, Clinton aides and fundraisers say, is an approach instituted by Cheng that mirrors the data-heavy, no-drama tactics of Barack Obama’s 2008 campaign, instead of the chaos of her own effort. Then, fundraisers who worked for the Clintons say the finance team spent endless hours on the phone schmoozing with donors while the needs of the actual fundraising staff stationed around the country went largely ignored. Now, one veteran of both campaigns told The Daily Beast, “If I call, Dennis calls me back within the hour. Now don’t get me wrong—he only spends three minutes on the phone with me, but he calls me back right away.”

Despite all the focus on online fundraising over the last several cycles, campaigns still largely raise money the way they have for generations: getting their most committed supporters to “bundle” money together from their well-off friends.

Since donations are strictly capped, the more you bundle, the more you rise in the fundraising hierarchy, and the more likely you are to get your phone calls returned from the candidate. In 2008, new donors were often “claimed” by multiple bundlers as being “theirs,” a practice that was encouraged by the campaign.

No more. Instead, bundlers are largely limited to only count toward their total someone they personally solicited to give. The new system fosters more competition, as fundraisers have to hunt the dollars on their own, rather than rely on their own network of bundlers. A computerized system keeps the whole apparatus in place. The directives are clear.

“From the first day he gave us pretty clear marching orders,” said one donor. “Ten checks of $2,700 in the first 30 days. If you wanted to be a part of it, you had to step up. There are very clear benchmarks.”

In order to be on the finance team, you have to bring in the money. No one is grandfathered in due to a long relationship with the Clintons, and titles, roles, and recognition are kept to a minimum.

“You are dealing with some fairly significant personalities here, people at the highest levels of entertainment and business,” said Tom Nides, a colleague of Cheng’s at the State Department and a Clinton adviser. “These people wanted to be treated well, but you need to send a message too. Hillary has a lot of friends, but they are going to be treated equally. You want to see who is going to produce.”

Or, as another top New York donor put it, “You can’t really make it into Hillary’s inner circle at this point. All you can do is raise a lot of money and make Dennis happy.”