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I watched online as a college classmate went from disgrace to redemption in months. That’s when I found myself deep in the world of black-ops reputation management.


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:


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 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.


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