In mid-2011, Tucker Carlson’s digital media outlet The Daily Caller was looking for money, and it turned to one of the biggest conservative donors in the country. The conservative news site hit up aides to New York hedge-fund manager Paul Singer with a pitch for its new nonprofit arm, The Daily Caller News Foundation.

Singer’s team rebuffed the request. But emails obtained by The Daily Beast show that Daily Caller staff, including its co-founder and publisher Neil Patel, circled back with Singer’s family office on numerous other occasions over the subsequent four years asking for meetings and courting Singer’s financial support.

Carlson stepped down from day-to-day operations at The Daily Caller in late 2016, and now hosts a prime-time Fox News show. But last week, he and Singer’s paths crossed once more. Amid an all-consuming national debate over impeachment, Carlson devoted significant airtime to attacking Singer, his hedge fund Elliott Management, and the beneficiaries of his sizable political contributions.

Those many beneficiaries are a who’s who of Republican politics—just this year, Singer has donated $1 million apiece to Republicans’ House and Senate super PACs—making Carlson’s broadsides against Singer, delivered as they were on America’s leading conservative television channel, particularly noteworthy. It shows how dramatically the ideological center of gravity on the right has shifted in the Trump era in Washington, with prominent conservative voices pitted, occasionally, against their would-be patrons of yore.

Carlson’s segments on Singer focused in particular on Elliott’s minority stake in the sporting-goods retailer Cabela’s. Carlson alleged that Singer’s fund forced the company’s sale, costing thousands of jobs in the town of Sidney, Nebraska. Both Elliott and the mayor of Sidney disputed Carlson’s reporting, which portrayed Singer as almost single-handedly responsible for the town’s destruction.

“Why is it still allowed in this country? Because people like Paul Singer have tremendous influence over our political process,” Carlson said in one segment. “Singer himself was the second biggest donor to the Republican Party in 2016. He’s given millions to a super PAC that supports Republican senators. You may never have heard of Paul Singer. But in Washington, he’s rock-star famous.”

For Singer, the denunciation must have seemed particularly disorienting. As emails obtained by The Daily Beast show, it had been less than five years since Carlson’s news outlet last came to him looking for cash. Asked for a comment on the emails, a Singer adviser essentially accused Carlson of coming after the billionaire hedge-funder in retaliation for declining the fundraising appeals.

“There was no principle at stake here,” the adviser said. “This is how a protection racket operates—you pay Tucker or you become a target. And he now has a much bigger platform to pursue his vendettas.”

Carlson says he doesn’t even recall his company asking Singer for money. “I don’t remember having anything to do with that. I don’t think that I did,” he said. “But it wouldn’t matter anyway because, as I’ve said many times, my views about pretty much everything have changed dramatically in the past 10 years, based on the evidence. America’s changed and so have my views.”

The Daily Caller’s appeals began in June 2011, when Patel reached out to Singer’s office to arrange a meeting with Carlson. “We think what we are doing is having a big impact, especially on a per dollar basis,” he wrote. “We are also building out a real business with a direct ad sales team. Therefore, unlike most political dealings, an investment with us offers some hope of a return and maybe a very good one. We would love to discuss this at your convenience. Tucker comes up about once a week to host Hannity and I end up there regularly too so let us know if you are up for it.”

Later that year, internal Singer office emails indicate that a different Daily Caller fundraiser reached out to request a meeting between Singer and Carlson. “I called the woman back and she is kind of pushy,” a Singer aide wrote. “I asked her to send me a one pager on the project and she told me that it is so sensitive that they do not want to put anything into writing to send around (it’s something to do with going after Obama and the left)... I don’t think my ‘no’ was forceful enough.”

The pitches continued throughout late 2011 and early 2012. After a lull, they picked up again in late 2014 and early 2015. In one email, a Daily Caller representative assured Singer’s office that “funding is 100% deductible and there are no disclosure requirements.”

Patel told The Daily Beast in an email that he didn’t recall specific fundraising pitches sent to Singer’s team, and wasn’t aware of Carlson’s Fox News segments last week. But he added that he’d “be happy to pitch Paul Singer or anyone else short of a Jeffrey Epstein type character for funding to support the great work that Daily Caller News Foundation is doing to train young journalists.”

In the years since his departure from the Caller, Carlson has become arguably the most prominent voice in media for a new brand of conservatism that hews more toward policies embodied by the Trump presidency—a more restrictionist immigration policy, skepticism of free trade—and largely opposed by significant segments of the business community that have traditionally provided Republicans with much of their financial support.

His identity, fellow conservatives concede, reflects the change that the Republican Party has undergone as a whole in the age of Trump. Onetime “rock stars,” as Carlson put it, who previously financed or supported many of the conservative movement’s commanding heights now find themselves at odds with those holding power—both culturally and politically. And it’s created a tension between the donor class and the institutional leaders who have hit them up for money in the not so distant past.

“The reality is, political coalitions have just radically, radically changed since 2014,” according to Liz Mair, a Republican consultant and Trump skeptic. “You can find evidence of this in talking to family and friends and the man on the street, but you can also see it just as easily in looking at the media. The question is, will it prove to be a four- or eight-year aberration or is this indicative of a broader political realignment that will last for decades or longer?”

Carlson’s criticisms of Singer show just how big a shift the conservative movement has undertaken. Even as he was funding a push for the legalization of gay marriage during the Obama years, Singer rarely drew the ire of prominent Fox News hosts like he did last week.

In an interview Wednesday with Ned Ryun, a conservative activist who runs the nonprofit American Majority and a sister dark-money group, American Majority Action, Carlson agreed that no “self-respecting conservative” should take money from Singer or the political donor network associated with libertarian billionaire Charles Koch and his late brother David.

In a remarkable break with conservative orthodoxy of the past decade, Ryun even suggested that it might be time to roll back Citizens United, the 2010 Supreme Court decision that allowed corporate entities to spend money directly on political activity.

Among those very corporate entities is Ryun’s advocacy group. American Majority Action has spent extensively on politics, according to a review of its tax filings, even occasionally exceeding generally accepted thresholds on such spending by a nonpartisan advocacy group. In 2016, nearly 85 percent of its budget went toward “direct support” for political candidates, far more than the 49 percent that is generally seen as the upper limit for organizations barred by law from making politics their primary purpose.

American Majority Action is also largely funded by high-dollar anonymous donors. In 2017, one such contributor gave the group $500,000—its entire reported income for the year. Ryun said in an interview Monday that he doesn’t think his donors “give a rip” about anonymity, but said his policy is to keep them anonymous.

As for Citizens United, Ryun told Carlson, “I get some of the arguments for it, but it has also empowered the vulture capitalist class to buy a lot of politicians, and buy a lot of think tanks, who are advocating and implementing policies that are antithetical to the interests of the American worker.”

Singer is ground zero for that political influence, in Ryun’s view. So he said he was surprised to learn, given his vocal support for Trump, that he himself was featured in a six-figure donor pitch sent to Singer’s office in the heat of the 2016 Republican primary campaign. The $250,000 fundraising ask came from a nascent anti-Trump group run by Mair called Trump Card LLC.

Singer never financed Trump Card, and Ryun says he had nothing to do with it. But the pitch identified him as one of two “consultants who have expressed interest in assisting with this project.”