Lavish spending is part of Yiannopoulos’s brand, yet another bird he flips at correctness and decorum. In the midst of his Free Speech Week debacle, he told a reporter that he would hold a press conference on a nearby island, arriving on a speedboat while wearing a $15,000 fur coat. While Macris acknowledged that Milo Inc. is an “aspirational brand,” he said that luxury spending only accounted for less than 0.3 percent of the budget, and the fancy dinner parties were less than 0.5 percent. “I can assure you,“ he said, “the notion that every night, he and I are guzzling thousand-dollar bottles of Champagne and jetting around to penthouse suites—maybe next year, I don’t know.”

Milo Yiannopoulos follows police offers after his free speech rally at UC Berkeley on September 24th. By Justin Sullivan/Getty Images.

Meanwhile, Yiannopoulos has fallen short of some of the goals he promised for his ambitious, multi-pronged company. The Dangerous Books imprint has only published one book, which Yiannopoulos has not gone on tour to promote, and Free Speech Week was a P.R. disaster. Macris insisted the company is on schedule: “In fact, we are set to publish our next book, FATWA, by Pam Geller, on November 1.”

As for social media, the world where he first made his name, some have noticed that the investments don’t match the somewhat anemic content. “If he was pumping out a daily YouTube episode or some big, well-produced content, I’d be like, ‘O.K., money well spent,’” the frustrated associate told me. “For $10 million, you better be putting out, five times a week, quality content. Instead, he has a Facebook page where he steals memes and videos that he reposts with his logo on them.”

In backing Yiannopoulos, the Mercers appear to have made a calculation that backing the most audacious flamethrower, however flawed, will provide the most profound return on their investment. His antics, no matter how dreadful, could be construed as a form of free media, which makes up for any inefficiencies in the way he runs his business. The question, however, is whether their support of him ends up playing a tacit role in the overall devaluation of the far right. It’s a legitimate question, and one pondered at the very top of the far-right totem pole. A year ago, before his dalliance with Donald Trump began, Steve Bannon expressed physical discomfort to the writer Ken Stern about behavior in the deepest dredges of the movement. Whether he was horrified by the tenor of the conversation or the substance, Bannon, a Harvard M.B.A. and Goldman banker, knew that it was bad for business. If the far right wants to move beyond a fringe movement and into its own mini-industry, it needs credibility.

Yiannopoulos, for his part, seems unbothered. He is currently scheduled to go on tour in Australia, and given the logistics of running his company—including the problem of paying one’s employees—the Mercers are viewing this as a final test for whether Milo Inc. can ever be sustainable with the personality at the helm. “They are taking profit seriously,” said my source with knowledge of their funding activity. “It’s not just a front group for political opinions, but only time will tell if people think they can still get something out of Milo.”

Meanwhile, several other young conservative groups are hoping for some Mercer largesse to fund their own projects, with a select few voyaging to their Owl’s Nest home to meet with the family and try to lock down a deal. “They should be doing stuff with conservatives who have a millennial audience,” advised Cernovich, listing several up-and-coming conservative younglings: Charlie Kirk, Steven Crowder, Lauren Southern, even, perhaps, Tomi Lahren. “They heard about Milo and really jumped on the Milo train, but I don’t think they’ve heard about these other people.”

Yiannopoulos’s salvation may be his social cachet within the limited slice of the conservative world he inhabits: no one is as notorious, charismatic, or as much of a train wreck as he is. The industry professional compared Yiannopoulos to Kanye West in that regard—“Part of the Kanye fun is waiting to see what he’s going to say next, or when is he going to screw up next”—and, moreover, no one is ready to supplant him. “You couldn’t pick somebody out of Breitbart and go, ‘YOU’RE going to be the next Milo!’ It doesn’t work that way . . . And if you tried to do it, everyone would go ‘yeah, you’re not really Milo.‘”

The way the Mercers see it, however, may be that Yiannopoulos will be but one trial balloon in their attempt to accelerate the culture war, and if he fails, they can always fund another. Ten million dollars, after all, is but a drop in the bucket to a billionaire. “He runs a hedge fund,” my funding-familiar source explained of Bob. “It’s a hedge.”