There is one thing Mike Pence does that drives all the Republican megadonors wild and gets them worked up enough to write $50,000, $100,000, even quarter-million-dollar checks: He listens, intently.

He looks you in the eye and asks you personal questions: How is your oldest son doing after returning home from deployment to Afghanistan? He appears interested while you talk about your bright idea to improve the Health and Human Services Department.

On a particularly swampy day in Washington, D.C., this past September — mid-80s and stagnant humidity, hot enough to sweat through the Joseph A. Bank standard two-button the vice president favors — Pence drew almost 100 people to meet his older brother and encouraged them to give him their money.

Greg Pence, 61, who shares his 59-year-old brother’s shock-white hair but has a longer face and slightly beadier eyes, is running for the vice president’s former congressional seat in Indiana’s 6th District.

At the Pence brothers’ fundraiser, hosted at the National Restaurant Association’s lobbying headquarters, a few blocks northwest of the White House, Mike Pence worked the room full of Washington lobbyists and moneyed Hoosiers. He took on small groups of two and three donors at a time, giving a few minutes to each one and making sure to hit them all. But when Pence turned to speak with an individual donor, the room melted away. Suddenly, it was just the two of them — nobody else — Pence locked in a very serious but warm gaze.

Greg appeared a bit more shell-shocked — this is his first serious foray into politics, and he hasn’t done a lot of so-called grip-and-grins. His wife, Denise, however, was a natural, darting between groups.

Mike Pence, the younger and more charismatic brother — a political animal comfortable among the rich and powerful — is a side of the vice president that the public rarely sees. Onstage, his Reaganesque winks and nods look canned, corny. But in person, it all comes across as genuine. This is how he taps into billionaire bank accounts.

A political animal comfortable among the rich and powerful is a side of Mike Pence the public rarely sees.

In a town made up of opportunists — people who look over your shoulder mid-conversation to see if there’s someone more important than you that they need to attend to — Pence has the political bedside manner of some of the best in the business (think Ronald Reagan, Bill Clinton, and Joe Biden). But unlike the “I feel your pain” Clinton, Pence invites more of a one-way conversation: He sits there and takes it all in, rarely interjecting.

A month of observing the vice president on the donor circuit and more than a dozen interviews with Republican political operatives, donors, activists, and congressional staff reveal a new vision of Pence halfway through the Trump administration’s first term: the GOP’s “donor whisperer.”

September started with a jaunt through Florida, fundraising for Republican U.S. Senate candidate Rick Scott, then a trip to Nevada to raise money for the Republican Governors Association. Stops in Tennessee, Michigan, and other critical states for Republicans followed. When he wasn’t on the road raising cash, Pence was working the fundraising circuit in Washington, D.C., outside the White House.

Pence didn’t fall into the fundraiser role by accident. At the beginning of the year, senior White House staff approached President Trump and told him he’d have to let Pence do the heavy lifting on gathering contributions. The White House, and the GOP, needed somebody who would hit the stump every week and could pour days and weeks into endlessly soliciting donors — grooming and maintaining relationships that would turn on the money tap. Trump laughed and readily supported putting Pence in charge of that, recalled one Republican familiar with the conversation who agreed to speak on background. The president had never wanted to do the fundraisers anyway. He prefers the intimacy of gabbing with trusted friends or the validation of raucous campaign-style rallies. Plus, Trump is a germaphobe.


A week after his brother’s fundraiser, Pence is down the street at the Trump International Hotel. It’s the end of month, and the weather has flipped on its head, the heat and humidity replaced by a weeklong downpour. Pence, alongside the president, is raising money for House Republicans at a top-flight fundraiser. Trump is the big draw, and he doesn’t disappoint, delivering wild and disjointed comments on trade. But serious donors, like New York billionaire industrialist and investor Andy Sabin, came looking for Pence.

Sabin paid $50,000 to get in tonight, and he wants to “bend Pence’s ear” — grab him for a minute for his pet issue: a plan for the future of the GOP.

After a few minutes, Sabin finally gets Pence alone for a minute and makes his case: The Republicans need to remember why Teddy Roosevelt made them so popular a century ago. They have to get back in the conservation game. Pence nods, he’s listening. After a minute, he asks for more information, and Sabin says he has a briefing paper, “A Return to Our Conservation Roots.” The paper outlines conservative environmental moves that, Sabin says, would appeal to moderate voters. Pence is interested; he’ll have his staff review it. “Send it to me,” Pence tells Sabin.

It’s not a guarantee that Pence will just do whatever Sabin wants, but (most) donors don’t think that way. Rather, it’s a promise that he will consider it, and that’s enough for a heavy-hitter like Sabin.

Getting a single message to sink in with voters is vastly more expensive than it was in the previous midterm election battle, four years ago.

Pence’s money-raising skill in this field has its own drawbacks, as do all things prodigious in Donald Trump’s presence. When the vice president launched his own super PAC last year, just a few months after taking office, it raised a few eyebrows. He started hosting high-dollar dinners at his residence, and a joke began circulating among the politically connected about who was running for president in 2020: Trump or Pence. After the New York Times published a pair of articles revealing Pence’s hyperactive fundraising, he anticipated the rage of the president, who doesn’t ever want to be upstaged — so he jumped out in front of it, calling the reports “disgraceful” and an affront to the entire Pence family.

But the stories of Pence’s mad fundraising weren’t wrong; they were dead-on: Pence’s chief political operatives, Nick Ayers and Marty Obst, had been shopping lunches and dinners with the vice president to donors across the country. One donor the pair contacted last year said he was quoted a price of $75,000 for an exclusive lunch or dinner with Pence (the details were still being hammered out). The donor declined the offer but also thought little of it. That’s par for the course in D.C.


Pence can thank the president for the endless drumbeat to collect more Republican cash. Trump is a lightning rod unlike any the party has ever seen before, all of which has driven Democratic fundraising to new heights.

To fight them off, the GOP has raised an incredible fortune. Pence’s PAC alone has raised $2.9 million in the past two years and spent $2.5 million of that money, according to OpenSecrets’ collection of Federal Election Commission figures. Protect the House, the joint fundraising operation run by House Republican leaders and Pence’s team, has raked in close to $14 million and doled out $11.4 million, according to OpenSecrets. And those numbers don’t capture the fundraising Pence has done for the Republican National Committee, the Republican Governors Association, and individual candidates across the country.

But in the age of Trump, it takes an incredible amount of money to break through for a midterm election cycle: Combined, House candidates have raised $1.1 billion for the midterms so far and $626 million for all the Senate candidates. Cash totals like these are usually reserved for presidential cycles.

A Democratic operative working on Senate races blamed the rising cost of business on the 24/7 Trump reality TV show. Political coverage is so omnipresent and schizophrenic (reflective of a bonkers presidency) that getting a single message to sink in with voters is vastly more expensive than it was in the previous midterm election battle, four years ago.

All of which explains why Pence is out, a lot, fundraising. This past May, he did a daylong trip to New York City with Todd Ricketts, the finance chairman for the Republican National Committee. He packed the day with four fundraising events — the first with a small group of about 25 people, the second with 50 people. Then came the actual fundraiser itself, about 100 people. All that was followed by a dinner with Pence and Ricketts for the biggest Republican donors.

Vice President Mike Pence takes a phone call on Capitol Hill on Sept. 5, 2018 in Washington, D.C. Photo by Zach Gibson/Getty

A New York Republican fundraiser described the nonstop effort to raise funds as insurance against the upcoming election. “If that’s the blue wave outside, this is the giant red wall it’s going to crash against,” the fundraiser said.

But Pence and the Republicans have limited time, limited money, and a bigger spread to cover in the 2018 elections than usual. Retirements and departures — the House has seen 50 Republicans move up or move out—are a bad sign for them. The last man to lead a Democratic wave to overtake the House, Chicago Mayor Rahm Emanuel, was in Washington a year ago counseling Democrats on how to build a similar movement for 2018. Top of the list, he said, were retirements. Force Republicans to vacate seats, make it so miserable to seek reelection that they create open seats. It’s easier to win an open seat than beat an incumbent.

The power of having the vice president out on the stump isn’t lost on veteran operatives, and certainly not Pence himself.

All of this, the extensive work with little time, has strained even Pence’s capabilities. On a rainy day in the middle of September, Pence hunkered down with a leader and friend from the pro-life movement. The goal was simple: pick out where they needed to go, and do it fast. He was on a tight schedule, and they also had other business to talk about.

They met with a handful of their top staffers in the basement of the West Wing, in the Navy Mess, the mahogany-paneled dining facility next door to the Situation Room. If the most serious national security measures happened on the other side of the wall, this was a small war counsel of the gravest political importance: How do you marshal the vice president’s limited time for a strategic deployment with less than six weeks until the election?

Florida’s a clear pick: With two major statewide battles — between Republican Governor Rick Scott and Democratic Senator Bill Nelson for Senate, and Democrat Andrew Gillum and Republican Ron DeSantis for governor — make any time there worthwhile. They could pick a swing district and help a House candidate, too. It would be time well spent now, and it would carry dividends into 2020 — which was part of their long-term planning during the meeting.

Pence opened the huddle session by raving about John James, the Republican Senate candidate in Michigan. The vice president became animated in a way he rarely is in public. He was pumped about this kid out of Michigan. Young by political standards, eight years under his belt in the Army, staunchly conservative, and black. But, and this is the big but of campaigning, maybe the race was too far out of reach for his new friend.

Despite not being as big a draw as the president, the power of having the vice president out on the stump isn’t lost on veteran operatives, and certainly not Pence himself. Barry Bennett, a former Trump campaign adviser and veteran Republican strategist, laughed and called it unfair for the lowly fundraisers out there trying to raise a buck. The amateur politician who wins big in November will never forget the time the vice president of the United States stood by their side. “You really develop a nice bank of friends who think they owe you out of it,” Bennett said.

One of Pence’s most cherished memories from his start in politics was when then–Vice President Quayle helped him on the stump in August 1990 at a Holiday Inn in rural Shelbyville, Indiana. Although Pence lost his 1990 race, he had Quayle’s back in an opinion piece two years later as chatter picked up that Bush might dump Quayle from his reelection ticket in 1992. Pence wrote that anyone other than Quayle would amount to a betrayal against conservatives.


When Trump invited evangelical leaders to the White House at the end of August, he warned them of violence if they fail him. “It’s not a question of like or dislike. It’s a question that they will overturn everything that we’ve done and they will do it quickly and violently. And violently. There is violence. When you look at Antifa — these are violent people,” Trump said in audio of the meeting obtained by CNN.

When Pence went out to address the broader Christian right political movement at the Family Research Council’s Values Voter Summit on September 22, he made the same pitch as Trump — but it came out as more of a genuine plea. The crowd loved it.

While the vice president’s call to action may have been a win for the White House, even in moments of success, Pence and his aides know that if he veers too far into the spotlight, he could lose his standing inside the administration, or worse: get replaced on the 2020 ticket.

All of which is why Pence is out working the room at the National Restaurant Association and hundreds of others rooms like it across the country. Trump rallies thousands at a time and banters for 45 minutes, but Pence does best in small spaces with fewer than 100 people.

And while Trump is out whipping up chaos and noise, Pence is in the quieter confines, where $50,000 or so will buy you his ear for a minute or two. And he is listening.