Republican Billionaires Just Can’t Seem to Buy This Election

Republican Presidential Candidate Jeb Bush Campaigns In Tampa
Photo: Brian Blanco/2015 Getty Images

You’d think buying an election would be easy. This is, after all, the rough pitch that political consultants deliver when persuading donors to part with their money. (It’s also the primary theme of Bernie Sanders’s presidential campaign.) The formula traditionally goes like this: Out-raise the competition, bludgeon them with attack ads, and watch the votes roll in. In the five years since the Supreme Court enshrined unlimited campaign contributions to organizations not directly affiliated with candidates, money has poured into the political system. And yet spending the cash haul effectively has never been more difficult.

Take the 2012 contest between Mitt Romney and Barack Obama. Celebrated political strategist Karl Rove assured a murderers’ row of Republican megadonors that, with enough funding, his super-pac could put Romney in the White House. “I had every expectation we would be the victors,” says Home Depot co-founder Kenneth Langone, who gave half a million dollars to Rove’s American Crossroads. In the closing weeks of the campaign, Crossroads circulated a top-secret presentation to a small group of billionaires that projected Romney could win a “mandate” if they contributed an additional total of $25 million to fund a “surge” of negative ads. A handful ponied up, and on Election Night, they assembled in Boston certain they would be watching their investment pay off.

Instead they watched Rove’s infamous Fox News meltdown as their $117 million grubstake went up in smoke. To many of the billionaires it felt like a mugging. A few days after the election, New York hedge-fund manager Daniel Loeb, who’d helped finance Rove’s surge, tried to sue Crossroads and Fox News for misrepresenting the facts. “Loeb felt this was like an investment bank committing fraud on a road show,” a friend of his told me. After conferring with a securities lawyer, Loeb discovered that there are no investor protections in politics. He never filed a suit. (And Loeb declined to comment.)

Rove’s 2012 crash is having profound effects on the 2016 Republican primary. To begin with, George W. Bush’s Brain is no longer considered much of a brain. “I gave Rove $500,000. What did I get for it? Nothing!” Langone told me. Two of Rove’s most generous 2012 funders, Texas billionaires Bob Perry and Harold Simmons, have since passed away, and their heirs have turned off the cash spigot. “Everyone is still shocked Romney lost,” says Simmons’s widow, Annette. “I haven’t committed at all.” So far this year, Crossroads has raised just $784,000, according to the Center for Responsive Politics. Rove insists he’s still a player. “We’ll be involved in the Senate races,” he told me. “Depending on who the presidential nominee is, we may be involved in that, but that’s a long way off.” What Rove is not is anywhere near the center of the Republican Party. “But for his perch on Fox News, Karl would be in political Siberia,” says a top Republican strategist. “The going joke is that he must have a picture of Roger Ailes in his underwear to keep his contract.”

It’s not just that Rove is personally marginalized. Donors have awakened to the realization that topflight consultants can earn millions from campaigns regardless of whether they win. “It bothers a lot of people that politics has become a cottage industry. Everyone is taking a piece of this and a slice of that,” says California winemaker John Jordan, a former Rove donor. “Crossroads treated me like a child with these investor conference calls where they wouldn’t tell you what was really going on. They offered platitudes and a newsletter.”

Working under the assumption that they can support a campaign better themselves, donors are building their own organizations, staffed by operatives who report to them. “A lot of people who felt betrayed in 2012 set out to build political structures,” says Kellyanne Conway, president of the pro–Ted Cruz super-pac Keep the Promise I, which is backed by hedge-fund billionaire Robert Mercer. Mercer is a prime example of the new breed of activist donor. This presidential cycle, he has donated more than $30 million to a quartet of pro-Cruz super-pacs. A computer scientist by training, Mercer is also part owner of a political data firm called Cambridge Analytica, which boasts on its website that it employs “psychographic profiling” to recruit voters. As a result, Mercer’s pacs have shunned the traditional strategy of saturation TV coverage. Instead, Mercer is focused on targeted radio buys, digital outreach, and field organizing.

The savviest GOP candidates have capitalized on this shift. In fact, Cruz’s campaign fund-raising apparatus seems designed to let donors roll up their sleeves. Cruz contributors can specify how they want their money spent, much in the way universities allow benefactors to earmark their donations for a new science wing or aquatics center. “If you’re a donor, you can say, ‘I want to see this money used for Iowa,’ ” one strategist told me. “It’s a way to entice donors. They look at it like fantasy football.”

The new billionaire-backed operations style themselves as models of superior sophistication. During the last Republican primary, Sheldon Adelson bankrolled Newt Gingrich’s campaign essentially by writing blank checks with little or no oversight. Compare that to the super-pac funded by Chicago Cubs owner Joe Ricketts, who has his own political staff and demands accountability. “I’m used to saying the Ricketts’ spend their super-pac money like it’s their own money — because it is,” the family’s political adviser, Brian Baker, told me.

Or look at the network being built by Elliott Management founder Paul Singer. In 2014, Singer created the American Opportunity Alliance, a group of roughly 40 Republican financiers who gather regularly for secret meetings with candidates. This fall, Singer threw his weight behind Marco Rubio and urged his members to do the same. In the general election, Singer will be a player with America Rising, the opposition-research firm headed by Romney’s dark-arts wizard Matt Rhoades. Instead of funding TV ads, Rhoades’s group offers Singer more predictable returns: It is narrowly focused on digging up dirt on Democrats, for example by sending video trackers to events in order to build a library of unflattering material.

It’s all about retaining control. In October, billionaire investor Carl Icahn announced he was launching a $150 million super-pac to lobby for corporate tax reform. “At the risk of being immodest, we have one of the best records on Wall Street. And I like doing things myself,” he told me. “Too many cooks spoil the soup.”

John Jordan now supports Republican candidates through his own super-pac, which applies the lessons he’s learned from winemaking. He, too, is backing Marco Rubio. “I know really well how to sell things. I make my own ads,” Jordan said. “The quality of ads produced by most of the ad-makers is just so bad that they’re ineffective. Have you looked at Jeb’s ads? They’re terrible! It’s unforgivable.”

Perhaps Bush is the perfect case study: The candidate who has underperformed the most is the one with a 2012-style campaign, who steered all his major donors into one super-pac. That organization, Right to Rise USA, is run by the grizzled strategist Mike Murphy, who succeeded in bundling a $100 million war chest and is now finding himself on the receiving end of donor backlash. Last month, for instance, a group of major Bush supporters held a conference call to vent about Murphy after he outlined his strategy in an interview to Bloomberg Politics. “These guys got rip-shit,” said one person briefed on the call.

But the most important lesson the billionaires are learning this year is that they aren’t much better at politics than Karl Rove. Well, not true. There is one billionaire who seems to have contemporary Republican politics figured out. “This is no longer a meteor going through the sky,” Langone told me, observing Donald Trump’s dominance over the race and sounding just shy of panicked. “He’s been in the lead 116 of 120 days.”

*This article appears in the December 14, 2015 issue of New York Magazine.