Nesbitt, who started and heads an airport parking company, doesn't come to the Vineyard, although the friends hope to get him here sometime. But on Obama's other annual getaway, in his home state of Hawaii, they're all together again.

Nesbitt and Whitaker also turn up frequently in Washington, sometimes at unexpected times. The day after Obama struck a deal with Republicans in April to avert a government shutdown, he paid a quick, unannounced trip to the Lincoln Memorial on the National Mall to show that the nation's parks and monuments were open for business. Whitaker was at his side, and the two bounded cheerfully together up the imposing stone steps.

The core group met and cemented their relationship through various Chicago connections, including ties at the University of Chicago, where Nesbitt and Michelle Obama's brother attended business school together. Jarrett first met the Obamas in 1991, when she hired Michelle, then engaged to Barack Obama, to work in Chicago Mayor Richard Daley's administration.