Photo: Bobby Doherty/New York Magazine; Patrick McMullan (Upham)

On November 29, 2010, federal agents in San Francisco arrested a 33-year-old New Yorker named Samuel Phineas Upham, setting in motion the chain of news reports that are responsible for Google’s auto­completing his name in the following ways:

PHINEAS UPHAM TAX

PHINEAS UPHAM ARREST

PHINEAS UPHAM INDICTMENT

The case against Upham, who goes by “Phin,” was laid out by Preet Bharara, the financial-crime-fighting U.S. Attorney. The indictment alleged that Phin tried to cheat the IRS by conspiring to hide over $11 ­million in Zurich at the Swiss bank UBS, and helped his mother, Sybil Nancy Upham, sneak the money into the United States. It said Nancy Upham, with the aid of UBS advisers, started a sham Liechtenstein nonprofit, the Rivaro Foundation, in 1993, then a sham Hong Kong corporation, Grand Partner International Limited, and, when UBS began cooperating with the IRS, moved the accounts to a bank in Liechtenstein without a U.S. branch. In 2005, Nancy directed Phin to go to Zurich to secretly retrieve some of the money in cash. He went, in 2005 and 2007, bringing back amounts as large as $300,000.

Nancy pleaded guilty and was sentenced in April, paying half the hidden money in penalties and receiving a three-year suspended sentence. Phin was both more and less lucky. In May 2012, Bharara dropped the charges, but the Google stain remains. Bloomberg’s headline, one of the most prominent in the search results, said Phin was “accused of helping Mom hide money,” and so even with the Jason Bourne–like cachet of having traveled around Switzerland with a bag full of cash, Phin still seemed, to those who Googled him, like a 33-year-old errand boy for his mother, herself an inept financial criminal. It was an especially cringe-inducing Google Easter egg for someone like me, who’d gone to ­college with him.

I’d known Phin slightly while at Harvard, where we both studied philosophy. A graduate of the Collegiate School, he dressed preppy and was a member of the Harvard chapter of the Ayn Rand cult. In the one seminar we shared—led by libertarian philosopher Robert Nozick—Phin bloviated weekly, reminding me even then, before I knew that his mother would hide from taxation more money than I will make in a lifetime, of the serpentine crew of rich kids who tried to send Chris O’Donnell up the river in Scent of a Woman. I wasn’t poor, but no one in my family knew how heavy a bag with $300,000 in it felt.

So as a taxpayer and a jealous prole, I watched his downfall with special interest, and even set up a Google Alert to keep abreast of developments. The first hits came in February 2012. “Phin Upham appointed Head Finance Curator of Venture Cap Monthly,” said one press release. Other accolades came through periodically—little appointments he garnered at this or that magazine or website. Writing professionally isn’t easy, I thought, briefly impressed.

Online, Phin’s financial journalism found a nice complement in philanthropy. My e-mail pinged with a press release issued when Charity News Forum named him “Philanthropist of the Month” in November. Another told me he was writing for something called Philanthropy Chronicle, an online charitable-­giving portal I had never heard of. What’s more, he was rekindling his passion for analytical philosophy, publishing a collection of essays from The ­Harvard Review of Philosophy, the undergraduate journal he once edited. And he was even combining philosophy with philanthropy, leading the small staff of the website PhilosophyBookReview.com to “bring philosophy writing to underprivileged youth by making it part of nonprofit educational programs in developing nations.”

But something was wrong with these sites, which in every case looked flimsy and temporary, especially when you got beyond the first page. Venture Cap Monthly listed a number of prominent writers as “authors,” including the Financial Times columnist Christopher Caldwell, Fast Company journalist Danielle Sacks, and Slate critic-at-large Stephen Metcalf. Caldwell and Sacks write about business, so I could imagine—­barely—that by contributing to an obscure site, they might be slumming for a paycheck. But I couldn’t make any sense of the presence of Metcalf, who had written a ­scintillating essay about the films of Tom Cruise, I remembered, but nothing that would interest a venture capitalist.

Now each ping made me a little more suspicious. None of the articles by or about Phin mentioned donations, which I expected would be a major aspect of philanthropic work for someone who came from a family rich enough to hide $11 million from the Feds. And when I looked at Charity News Forum (another curiously bare site, more like a derelict blog), I saw that Phin’s name was listed as a contributor alongside a few semi-­prominent voices in philanthropy, as well as … the journalist Ron Rosenbaum? That seemed odd, given that Rosenbaum doesn’t write regularly about philanthropy and is best known for a book about Hitler.

Back at Venture Cap, I clicked on Caldwell’s and Metcalf’s names and found they led only to brief excerpts and links off the site. Neither had ever contributed a full story. Only the name “Phin Upham” linked to actual full-length writing—and it was all terrible stuff, much of it seemingly recycled from high-school term papers. I found another press release from six months earlier also announcing his appointment to Venture Cap. When I went to the street address listed for the magazine’s offices, I discovered that 64 Prince Street did not exist—or, rather, that it is a back entrance next to an Indian restaurant.

All of these pop-up websites had a few things in common. They praised Phin Upham; they listed him among other distinguished figures; and, in naming them, seriously overshot the mark. One economic site listed him with Nobel laureate Alvin Roth and another with Fed chairman Ben Bernanke and Google co-founder Sergey Brin. Phin shared the marquee on a philosophy site with the late Stephen Jay Gould. And the site that boasted that Phin would be promoting philosophy education in developing countries claimed New Yorker editor David Remnick as an “author.”

By now I knew that I had found a vast web ecosystem built almost entirely out of bogus claims and associations. I counted 33 sites in all, most with their own logos and unique design. Someone had worked hard to create these sites, however shoddy or amateurish their content seemed, and yet they were worthless except as vehicles for Phin Upham’s reputation on the web—­perhaps worthless even in that way, since it didn’t seem possible they’d fool anybody for very long. If Phin paid for these sites, then it would appear that the manner of his contrition exactly matched the manner of his mother’s crime. She made up fake entities to hide their money, then he made up fake entities to salvage his reputation.

At this point, I was in full bloodhound mode. I downloaded the raw HTML code of each site and looked for evidence of a common author. I found it: They all used similar metadata to guide search engines: ­something like “{phin, phineas, samuel, phin upham}.” In the registration, some sites listed the same address, “123 Bay Forest Drive, New York, NY 10011,” and a ­contact name, “Xander Fields.” But the address doesn’t exist, and the phone numbers led nowhere. And I couldn’t find any Xander Fields.

But when sleuthing through the metadata, I noticed other names thrown in incongruously: Joe Ricketts, Helen Lee Schifter, Irena Briganti, Antonio Weiss, and Luke Weil. I also noticed the same Wikipedia editor, Belkin555, had tidied the entries of several of them. A few were powerful people with no apparent scandals to cover up: Joe Ricketts was the founder of TD Ameritrade, and Antonio Weiss runs investment banking for ­Lazard. Others, judging by the unforgiving kliegs of a Google search, had left much messier trails on the web.

Helen Lee Schifter, the first Google result informed me, was accused of carrying on an affair with the artist Brice Marden. One article, “Social Climber Beds Wrong ­Woman’s Famous Husband,” said Marden’s wife had approached Schifter in a West Village bistro, called her a tramp, slapped her, and received a spontaneous standing ovation from the other diners. (Schifter insists their relationship was platonic.) Irena Briganti is the vice-president of public relations for Fox News, and Gawker calls her “the most ­vindictive flack in the media world.” And then there’s Luke Weil, 33, whose father, Lorne, made a fortune in the off-track-­betting industry. In 2006, according to the Observer, Weil, who now works as a VP of his dad’s company and once sued the makers of the Born Rich documentary to force the removal of his own too-candid interview footage, assaulted a music producer with a broken liquor bottle and battered his then-girlfriend, Patrice Jordan, and was sentenced to a year in jail.

When I Googled the phone number on the press releases for Phin, I found that it also appeared on very-similar-looking press releases for Schifter, Briganti, and Weil—like Phin, they had been appointed to this-or-that editorial board, and the releases praised them for their intelligence and ­generosity. One celebrated Briganti’s work in history, and said she’d studied at Brown; in fact, she’d gone to suny-Albany, where she’d majored in communications.

Whoever he was, it seemed that “Xander Fields” had built a whole Potemkin universe of positive-press websites that amplified made-up praise, often by made-up people, for a handful of rich folks with messy online reputations. I was now deep down in a ­rabbit hole but hadn’t yet landed with a ­satisfying thud. Who was “Xander Fields”?

Pondering that X, I spelled his name with Scrabble tiles and scooted the letters around my kitchen table. The first words I came up with: SLANDER FIXED.

Ten years ago, on our first date, a woman looked at me with terror when I told her that I had Googled her and found the designer-shoe company she ran on the side. The look said: What else do you know? But sometime in the last decade, the ­practice of furiously Googling people stopped being creepy and became standard operating procedure. Today, the market in online-­reputation management is ­estimated to be nearly $5 billion, with hundreds of companies devoted to monitoring, improving, and even policing your online profile. The most famous of them, Reputation.com, advertises on NPR and charges in the low ­thousands of dollars for a basic scrubbing, which involves creating factual but flattering social-media accounts and websites, and more for bespoke guidance about how to protect your reputation online.

That work is not really any slimier than the work of PR firms offline—relentlessly accentuating the positive and hoping no one asks about the negative. But in the digital world, with anonymously registered websites, it’s easier to create natural-­seeming whisper campaigns, positive or negative, and disavow any role in them. Michael Zammuto, president of Reputation Changer, founded in 2010, says he has seen numerous clients try to beat Google by flooding the web with junky self-­glorifying sites. “These strategies never work over the long term,” he says. “There are no shortcuts.”

In the early days of the web, when ­average users and search engines weren’t great at discerning which sites were reliable, it really might have been possible to bury your indiscretions with pop-up web pages that extolled your virtues. But that Wild West of unreliability slowly gained its own kind of law and order, with the web professionalizing, commercializing, and socializing its way out of disreputability.

Now we have a web that users trust more because they think (correctly) that the Google era has weeded out the liars. But what makes the web more credible also makes it more vulnerable since users’ trust is again ripe for manipulation. Weirdly, the Phiniverse thrived on the assumption that people like me would not look at it too carefully. These were white-noise websites, engineered to drown out an ugly signal and designed perhaps less for discerning human readers than for search-engine robots, which organize and curate all the information users discover via search. Bumping just one negative news story off the first page of results with a positive notice might seem like a trivial achievement, but Google’s algorithm is sharp enough now that users assume anything interesting will appear on the first page.

The sites devoted to promoting Phin struck me at first as quixotic, since they were in direct opposition to everything I knew about the web—built on the principle that it could be used to conceal rather than reveal; that it could be tamed, mastered, and tricked. I felt sure that the web of the social-media era had natural immunity to these manipulations. About the big data web of tomorrow, I’m becoming less sure.

Phin maintains one relatively straightforward site, phinupham.com, and its ­registration included a New York phone number and the address of his family’s home, an $8.5 million West Village townhouse. He was confused but friendly when I called him, told him my name, and said we had met in a philosophy class. “How are you doing,” he said, omitting the question mark and clearly not remembering me. “Did we have a call scheduled?”

I told him no, and that I was a ­journalist and wanted to talk to him about all these press releases and accolades. “No,” he said. “I’m not interested.” I said that I had been doing some investigating and that I thought he had paid someone to AstroTurf the web to conceal his past. “I don’t want any part of any story,” he said. “This last year has been very hard on me and my family.” Then he refused to say more.

In searching for a new lead, I returned to where I started: the websites, most of which were registered anonymously or with fake details. I figured that the Phin campaign had improved with time and that whoever had orchestrated it was more likely to have slipped up earlier. The first site registered, just days after Phin’s arrest, was phinupham.com, and there I found a link to a real address: bryce@metalrabbitmedia.com.

Thud. At the bottom of this reputation rabbit hole was a rabbit—apparently a metal one. The e-mail address led me to a stylishly austere website for a PR firm that specialized in online-reputation management. “Bryce” was Bryce Tom, 32, a spiky-haired Californian who had previously run the online-reputation section of Rubenstein Communications and founded Metal ­Rabbit Media in 2011.

I e-mailed Tom and set up a call. He was cagey about what he said but in some ways fairly up front. Metal Rabbit Media, he said, was a boutique shop for the online reputations of very wealthy people. He worked by mining the client’s history of publication and philanthropy, then pumping up the volume to drown out all else. Basic service costs $10,000 a month, Tom said, which could make Phin’s total bill, running from the first website in December 2010, nearly $300,000. (Which made me think: Just who was scamming who here?)

Many of his clients had dark pasts, Tom said, and would come to him to get rid of the problem. He said he began by managing expectations: “The name of the game really isn’t completely getting rid of it,” he said. “But if it’s just a stupid incident, there are ways that you sort of push it down so it’s not the first thing people see when they Google you.” He called the possibility that someone might notice the manipulation “our nightmare scenario” and told me “the ultimate success for us is cleaning up the bad stuff without anybody noticing.”

When I asked Tom for a client who would speak to me anonymously, he said none would. But my list of suspected clients included at least one man I thought might talk, and I e-mailed him to arrange a call. When I mentioned Metal Rabbit, he fell silent, but ultimately he agreed to speak if I didn’t use his name.

I’ll call him Chad. (Unfortunately, his anonymity is blown, since his real name appears on several websites in the Phiniverse.) He is in his thirties and is probably the most sympathetic client imaginable for a company like Metal Rabbit. A foreigner now studying in the United States, he has a distinguished record of public service overseas, including in war zones in the Middle East. But when you Google his name, that record doesn’t quite overwhelm the screeching of a single hate site, which he says a jilted ex-lover posted to expose his alleged affairs. The site is semiliterate and unhinged. Its stated purpose is “TO REVIEW AND STUDY THE DEMONIC BEHAVIOR OF [CHAD],” and it prays that the Taliban will castrate him.

When Chad and I spoke, he was on holiday in his home country, and I could hear a lovely breeze and the swaying of trees on his side of the phone. The woman in question, he said, was his girlfriend from over seven years ago, and the breakup was acrimonious. “She was stalking me and stole a bunch of my shit,” Chad claims. Then, a few years later, Chad says he found the website and felt enough shock and pain to reach out to Metal Rabbit. He couldn’t afford a Phin-scale reputation offensive, but he paid “three or four thousand dollars a month” for a “fire-drill service” that would give his online presence an emergency scrubbing—a positive PR campaign that resembled those conducted by Metal Rabbit’s more scrupulous competitors. Like the rest of Metal Rabbit’s clients, Chad seemed to have an abhorrence for the anarchy of the web and a wildly optimistic faith in reputation gamesmanship—as though bad information online could be swept up with just a PR hack and a digital dustpan.

“Honestly, the only motivation is my kids,” he says. “It’ll be upsetting to them to see their father talked about like this.” He said that he considered suing, but since the site was posted anonymously, he found he had no one to sue. “You don’t understand,” he said. “She writes one blog post, and I have to spend years living with it. This is asymmetric warfare.”

I sympathized with Chad, and could even see worthiness in Tom’s efforts on his behalf. But when I thought about Weil or Phin, I wanted to ask why Tom would act as the servant of people whose characters committed public suicide long ago.

Tom suggested a meeting at City Bakery in the Flatiron district. He was recovering from the flu but showed up a few minutes early. His voice sounded congested, and over the course of our conversation, it got softer and retreated further up into his sinuses. We sat upstairs, teapot-to-teapot, and I eased into a conversation about ethics.

“We’re not putting press releases out there willy-nilly that aren’t true,” he said boldly, describing his clients as victims, and himself something like a defense attorney hoping for a hung jury. When I asked Tom if he ever had a client too loathsome to deserve his services, he said, “I haven’t come across a completely unsavory character,” then added, “I would say it’s not my place to judge.”

When I told him I had made contact with one of his clients, he was confused, then spooked. “How?” he asked, with the frightened look of a man who realizes he has left a gas burner on at home. I said I thought I knew the names of several clients, and he appeared stricken while he declined to comment as I listed them, one by one.

“This could be very bad for me,” he said, visibly shaken. “No one’s going to want my business.” We stared at each other in uneasy silence for a few minutes, and I fetched him a nonalcoholic sangria to calm him down. When I returned, Tom had shredded his napkin.

“Just tell me,” he asked as he stood up to go, “did you come upon these names because of something I said to you on the phone?” He said he’d be haunted forever by the guilt of having let a name slip. I told him no. The websites had been evidence enough.

Before we parted, Tom cautioned me that not every suspected client was technically a client. I had named the Hollywood director David O. Russell, for example: Favorable mentions of his recent film The Silver Linings Playbook are all over the Phiniverse, and Russell did have a recent slew of embarrassing press for having allegedly groped his pre-op transsexual niece in Florida. But Tom implied that Metal Rabbit may just have worked on the marketing of that film, and the Weinstein Company confirmed that he handled some of its social media. (Someone who works with Joe Ricketts of TD Ameritrade confirmed that he is a Metal Rabbit client, but insisted he only paid for web design and maintenance, not reputation management; a spokesperson for Weil claimed he had paid Metal Rabbit to “ghostwrite” for sites he said he had no reason to believe were illegitimate; Antonio Weiss, Briganti, and Schifter could not be reached for comment.)

When I asked why Irena Briganti would claim to have attended Brown University if she obviously didn’t, Tom implied that I shouldn’t be too quick to assume that an “Irena Briganti” I found online was a real person. He said that one service his ­company offered was the creation of doppel­gängers—fake Phins or Irenas or Graemes—so that one could never be sure whether the snark on the web referred to the fakes or to the misbehaving real McCoys. I imagined a future in which rich people create dozens of scapegoats for themselves, like Saddam Hussein with his body doubles, and wondered how some data-mining bot might tell the difference.

In the days and weeks that followed our meeting and my short phone call with Phin, both he and Tom told me that they couldn’t or wouldn’t speak to me again, and I made copies of the websites, expecting that Metal Rabbit Media would panic and edit their sites. But for months, the sites all stayed up, even the ludicrous ones that placed Phin’s ponderous musings on Atlas Shrugged and Kafka in the company of Nobel laureates. They were finally edited last week, but it was hardly a thorough track-covering.

Part of me sees this brazen shamelessness as just another expression of the privilege of extreme wealth and its certainty that money will heal all wounds—$300,000 is a lot of money to blow on a failed reputation-­management strategy. But it also happens to be the amount Phin was accused of smuggling into this country.

The persistence of these sites also makes me wonder: Are Phin and Chad the wild optimists about the Internet, or am I? I’d always assumed good information would crowd out bad online and that the arc of progress would bend toward truth. But the Metal Rabbit sites keep piling on, and the original tax-evasion stories are fading into the archives—last week, the fake and the real news items were still struggling for control of that first page of Phin’s search results. Of course, the only guaranteed, durable solution is one that Phin isn’t pursuing: publishing in journals that weren’t invented for his own greater glory, or giving away real money rather than paying others to pretend that he is. In the event that happens, I’m sure I’ll get a Google Alert announcing it.