The rumors that the Obamas will be vacationing on Martha’s Vineyard this summer have been spreading since April. Locals are famously ho-hum about these kinds of things, but even they admit that this could be an unusually crowded August on the island, with three sets of Democratic Party royalty descending at once.
The Clintons are expected to return to Edgartown, where they have often stayed at the home of Richard Friedman, a Boston real-estate developer. Caroline Kennedy will be at her mother’s former estate in Aquinnah. And while the Obamas’ plans are still unannounced, most people expect the First Family to settle on Oak Bluffs, at the northeast end of Martha’s Vineyard.
A few Vineyarders say they know whose home it’ll be. “The rumor is that it’s Wayne Budd,” says one, referring to the prominent Boston lawyer who was associate U.S. attorney general under the first President Bush. “He has a very large house with guesthouses that would be perfect for the Secret Service and his staff.” Budd has denied this, and a wealthy friend of the Obamas who claims to have been provided a photo of the chosen house says that the Oak Bluffs rumor is wrong. “The picture I received looks like it could be West Chop,” this friend says, referring to a neighborhood across the harbor. “But West Chop is totally white—so totally white that it would be a surprise.”
Even if the Obamas do choose West Chop, they’ll surely spend considerable time in Oak Bluffs, a town known for attracting most of the upper-class black professionals who stay on the island. As liberal as it is, the Vineyard is about as racially integrated as a college dining hall—blacks and whites get along fine, but they generally don’t socialize. “There’s not a lot of overlap between black and white,” says radio executive Skip Finley, who started vacationing in Oak Bluffs in 1954 and has been living there full-time for the past decade. “I don’t think anybody’s insulted by it. I’m certainly not.” It’s an arrangement that springs largely from the self-segregating impulse among black Vineyarders, who have come to the island to connect with each other. “We have people here who are black and upscale and racist,” Finley continues. “They don’t want to be around white folks, and they don’t have to.” By choosing to vacation in and around Oak Bluffs, the Obamas would be throwing a spotlight on one of the most demographically unusual towns in America.
In 1912, a former slave named Charles Shearer opened the first summer inn in Oak Bluffs that catered specifically to black patrons. Only a few dozen blacks visited the island at the time, but over the years Oak Bluffs has become the summer meeting place for scores of what could be called the Only Ones—black professional and social elites who travel in worlds where they’re often the only black person in the room. The Only Ones typically break into fields or companies that admit few blacks, move into neighborhoods where few blacks live, and send their kids to mostly white schools. They are not running from their own—they’re chasing after the best they can get. They aren’t assimilationist; they’re ascensionist.
Senator Edward Brooke, Congressman Adam Clayton Powell Jr., Ethel Waters, Paul Robeson, and Dr. Martin Luther King Jr. all made visits to Oak Bluffs. The novelist Dorothy West moved to the island in the forties, working for the Vineyard Gazette first as a file clerk and then, for decades, as a columnist who wrote about the prominent blacks visiting the island. Today’s summer vacationers come from the worlds of academia (like Harvard professors Skip Gates, Charles Ogletree, and Lani Guinier), media (NPR correspondent Charlayne Hunter-Gault, former ABC News anchor Carole Simpson), film (directors Spike Lee and Reggie Hudlin), and politics (Valerie Jarrett, who hosted the Obamas in 2007). “If you’re upper-middle class and black, this is your spot,” Finley says. “You’re going to find a way to spend a little bit of quality time here on this island.” In Oak Bluffs, the Only Ones become one of many. “I went to a garden party last weekend,” Simpson says, “and you would not believe the occupations of the people I met there. It’s like all the African-American East Coast professionals have chosen this place to socialize with each other.”
Not all blacks stay in Oak Bluffs; Vernon Jordan lives about fifteen miles away, in Chilmark. And the social scene in Oak Bluffs doesn’t exclude white islanders. Craig Hockmeyer, who owns a bicycle shop in nearby Vineyard Haven, says he spent many nights at Lola’s, which was, until its recent closing, a central part of the Vineyard black universe. “A bald white honky like me could go in there and feel totally comfortable and dance the night away with all the rich black folks, not a problem at all.” Still, Vineyard whites understand that blacks in Oak Bluffs take their socializing seriously. “I think the African-American summer community is more active in terms of the social network,” says Ron Mechur, a local real-estate appraiser. “They do more things, host more affairs, and support one another as friends. The white community doesn’t do as much, and they’re not as connected.”
The Only Ones deal with glass ceilings at work, unfortunate misunderstandings in their neighborhoods, condescension from blacks who think their education or class makes them inauthentic, and identity crises in their kids. When they get to their Vineyard vacation homes, they want to escape that casual, institutional, and intra-black racism and be around people who help them feel less anomalous. Trey Ellis, who wrote the script for The Inkwell, the notoriously bad film about the black Vineyard experience (Ellis himself called it terrible), says, “The black part of the Vineyard is like, I would imagine, being gay and going to the Castro. It’s this mecca where you can be yourself and be with people who have so much in common with you. No one has to feign some street cred when they’re playing tennis.” It’s a source of communion and of pride. “When you see a beautiful black family with their kids, it makes you feel really good about being black,” says Chrisette Hudlin, wife of Reggie and a lifelong Vineyarder who travels there every summer from L.A. “As a person who’s high-achieving and striving for the best for their family, you’re looking at these other black people who have the same goals, and it makes you feel good as a black person. You don’t feel out of place.” Several Only Ones say there’s nowhere in America that makes them more proud of black people.
This is particularly true among parents, who talk about the importance of introducing their children to other black upper-class families so they can know they’re not as peculiar as they might feel. “Black kids need to be around successful black families, because other blacks from humble beginnings want you to apologize for being successful,” says psychiatrist Carlotta Miles. “On the Vineyard, you don’t need excuses or self-consciousness or defensiveness.” Drew Dixon Williams grew up in Washington, D.C., where her mother, Sharon Pratt, served as mayor, and she spent summers on the island. “It’s sort of embarrassing to say this, coming from Washington,” she says, “but I used to say with a straight face—because I was too young to know better—that I would get my black experience on Martha’s Vineyard. I didn’t have to be defensive about not being black enough or being black in the first place. We were all from The Cosby Show.”
“The black part of the Vineyard is like being gay and going to the Castro. You can be yourself. No one has to feign street cred when playing tennis.”
Black Vineyarders say the island is one of the most liberal, open-minded places they’ve ever been. “On the racial stress test, I’d put the Vineyard at Canadian,” Reggie Hudlin says. Still, there are stories. Sheila Johnson, the billionaire ex-wife of Bob Johnson (together they co-founded BET), was once said to have been at a tennis tournament when a white woman asked if she would mind introducing her maid to some black people.
And while the Only Ones embrace each other, they can be dismissive of other blacks. “If you’re too Southern Baptist, too dark-skinned, too street, you might not be insulted by a white person but you may be insulted by a black person,” says Columbia law professor Patricia Williams. “It resembles the way in Britain race and class are inflected. If you’re a Nigerian prince and you speak the queen’s English, you’re okay, but if you’re an island hoodlum, then there are no bounds to the expression of racism.”
This kind of race-inflected class conflict flared up in the early nineties, when thousands of partying black undergrads moved the traditional Fourth of July party from Virginia Beach (from which they had been ousted) to Martha’s Vineyard’s South Beach. There were wild bacchanals full of public drunkenness, girls strolling around wearing very little, and guys ogling them with camcorders glued to their eyes or snakes wrapped around their necks. “Those parties were loud and raucous and not the typical Martha’s Vineyard crowd at all,” remembers one longtime black Vineyarder. “It was a different sort of person coming—the difference between Ebony and Jet, or between Marvin Gaye and Biggie.” To the Only Ones, the influx of hip-hop-blasting, beer-guzzling blacks felt like an invasion. As another person remembers it: “People had more grills in their mouth than their ride, and it blew up the island.”
A series of community meetings were convened. “No one said ‘Where all these loud niggers coming from?’ But that was the vibe from black and white Vineyarders.” In 1997, a solution was implemented that was simple and subtle enough to fix the problem while avoiding charges of racism: The ferry from Woods Hole changed its policy to eliminate standby passengers and to make reservations nontransferable. Party promoters could no longer buy tickets in bulk, and most students wouldn’t think to make a reservation months ahead of time. The parties moved elsewhere, and the Vineyard went back to business as usual.
The arrival of two presidents and a secretary of State will be an invasion of another sort. Some Vineyarders are nervous about the motorcades and traffic; others are preparing for a summer stimulus package. Many blacks from Oak Bluffs are elated that the Only One–in–Chief may be joining them. “People are going to lose their minds!” Tonya Lewis Lee says. At the same time, there’s also a bit of wariness among the wealthiest ones, an uncertainty whether Obama will affirm them. “Obama is more a man of the people,” says a Vineyarder who’s part of black high society. “He doesn’t seem to identify with affluent black people. His wife definitely doesn’t; she is basically a ghetto girl. That’s what she says—I’m just being sociological. She grew up in the same place Jennifer Hudson did. She hasn’t reached out to the social community of Washington, and people are waiting to see what they’ll do about that.”
It’s probably unfair to expect Obama to make new friends on this vacation. “They’re not trying to meet the billionaires,” says one person who knows the president well. “The Vineyard’s a place where everyone sheds their professional skin, and out there he does, too.” In the past, Obama has spent time playing golf with Vernon Jordan, swimming off South Beach, playing basketball, sitting on Jarrett’s porch while reading and watching the ferries, and taking the girls for ice cream on Circuit Avenue. “He’ll be Mr. Dad, as opposed to Mr. President,” Charles Ogletree has said. Surely he deserves it.