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.
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The Transformation of TV Into an Art Form
The Draw of Dream Worlds in Film
Gosselin, Prince of the Professional Nobodies
A Decade of Defining Moments in Pop-Culture
The Invention of New York's Local Cuisine 
Thirty-Five Short-Lived Looks of the Decade
Two Views of a Swath of the Upper West Side
An Older Generation Moves Into Williamsburg
Ten Years That Changed Everything
A Generation of Overparenting
The Sports Rivalry of the Decade
What Is the Point of the United States Senate? 
