A Most Proper Con

Just as Rockefeller had insisted on moving to Cornish, Boss demanded the family's 2006 move to Boston. McKinsey had transferred her to its Park Plaza office, and she already had a rental on Beacon Hill. The tension between the couple didn't show as they toured the $2.7 million townhouse at 68 Pinckney. As Reigh chatted with the broker, her parents decided that the five-bedroom house was perfect: It was at once grand enough to befit an executive reportedly making close to $1 million a year, and homey enough to raise a family in.

Rockefeller came to love his new neighborhood as much as his new home. From Hollywood to Wall Street, he had always been drawn to places that represented a sort of cultural shorthand for the best of their kind. He believed Beacon Hill was "the only choice for bluebloods," says a friend. Yet at times his grasp of status symbols seemed both shaky and hopelessly out of date. He once remarked that Chanel No. 5 was his favorite perfume, in a manner that suggested he was smitten most with the brand name. On another occasion, while shopping for a piano, he claimed to a friend that "Moonlight Sonata" was his favorite work. "It's such an overplayed piece, but it seemed like he didn't know any better," the friend says. But he'd learn. He started studying up on the history of the neighborhood and his home's location on the fashionable side of it. Rockefeller came to identify so closely with the community that he created a new e-mail address for himself: clark@beacon-hill.net.

On Beacon Hill he found people who were intrigued by his pedigree, but who tried hard not to show it. After meeting him on the street or at a party, where Rockefeller always introduced himself by his full name, it was not uncommon for strangers to Google him or mention to friends that they'd met a member of the famous clan. "The good thing about social climbing is that there is a viral aspect to it, where other people do the work for you," says a resident. Even as the boastful newcomer dispensed his stories in a decidedly un–New England way, his neighbors were quick to absolve him with the rationale that people of a certain status are allowed their little eccentricities. It's exciting to have a Rockefeller for a neighbor; his presence reinforces the idea that you live somewhere special. After all, a Beacon Hill without Rockefellers (or the Brahmin equivalent) might as well be the South End.

It wasn't long before Rockefeller was recognized up and down Charles Street. In the morning, he'd visit the Starbucks at the corner of Beacon—passing another Starbucks on the way—to get his tea at the neighborhood's busiest morning social center. At dinnertime, he often took his daughter to the Paramount café. Once, after a server there handed Reigh a children's menu, she handed it right back. "We are adults," she said. "We would like adult menus." Rockefeller also became a regular at Savenor's meat market, where he'd complain when his favorite lamb sausage was sold out. And everywhere he went, he was eager to display what he considered the appropriate local plumage. "He tried so hard to blend in," says one Charles Street shop owner. "But he weirdly stood out. He wore Nantucket Reds, whale-embroidered pants. He was a caricature more than anything."

Rockefeller's daughter won him a degree of respectability that he wouldn't have had on his own. When Boss and Rockefeller began sending Reigh to Southfield, an exclusive all-girls school in Brookline, Rockefeller would see her off to the bus stop, which is in front of the Hampshire House on Beacon Street. Several other prestigious private schools pick up children there, and the stretch of sidewalk has become a place where parents stay to chat after their kids are gone. There, in fall 2006, Rockefeller met a woman who he'd later call his best friend.

Emma (whose name has been changed at her request) is tall and slim. She dresses in designer jeans and peasant tops that make it tough to guess she is in her late thirties. The other parents weren't quick to approach her when she moved to the area with her new husband. "I think everyone thought I was a nanny," she says. "It's very hard to get into a new society. Clark was the first person who started to talk to me and brought me in." They began hanging out at the Starbucks after the buses left.

Over time, Rockefeller pulled into his orbit a host of other local characters who spent their mornings at the coffee shop. The group eventually named itself the Café Society, and its members would discuss art, culture, and politics, just like the Beacon Hill salons of yore. Rockefeller was admitted to more-traditional clubs as well, including the century-old Algonquin, where he was appointed one of 10 directors running a club of several hundred members. He's rumored to have joined the Sports Club/LA (one secondhand story puts him there working out in a Harvard sweatshirt, another college he periodically claimed to have attended).

To his growing list of affiliations, Rockefeller also added a few that revolved, ostensibly, around his daughter. He began reading to children at the Boston Athenaeum, and volunteering at the Clay Center observatory, a $16 million science center on the campus of his daughter's school named for Boston businessman Landon Clay. It couldn't have been lost on Rockefeller that Reigh provided him something of a social advantage. At the very least, she completed the image—certainly more effectively than the whale-embroidered pants did. Those who initially thought Rockefeller was, as one shopkeeper put it, "a weird loner," admitted their minds changed when they saw him with her.

In fact, other fathers on Beacon Hill came to envy Rockefeller's connection with his daughter. They noticed how he'd meet her at the bus stop and carry her on his shoulders all the way home. They would see him taking Reigh to karate classes at Hill House and sticking around to watch when some of the other parents went out to run errands. "Even the people who didn't really know him, knew him as a great father," says a neighbor. "Those of us who are fathers wished we could spend day in, day out with our daughters."

Rockefeller had hit the Beacon Hill trifecta: His name earned him notoriety, his wife's money bought him a residence on a well-regarded street, and he had a busy social life built around his little girl. "He was very much a part of the neighborhood," says a resident. "He was part of the fabric of Beacon Hill." It must have felt as if it could go on like that forever.