On Monday evening, the president and first lady spent the better part of two hours at a cocktail party at the West Tisbury home of Broderick Johnson, a lawyer, Clinton administration official and former lobbyist who served as a senior adviser on Obama’s 2012 campaign, and his wife, Michelle Norris Johnson, an NPR host.
And on Thursday, the first couple attended a soiree at the waterfront home of Brian Roberts, the Comcast chief executive, who has given tens of thousands of dollars to Democratic candidates and party committees.
On the golf course, the president’s partners included Washington power broker Vernon Jordan, World Bank President Jim Yong Kim, and Robert Wolf, an Obama donor and a key Wall Street ally. At a news briefing Wednesday, deputy press secretary Josh Earnest declined to comment when asked whether Obama had used the vacation to hold conversations about his forthcoming pick for the next chairman of the Federal Reserve.
The president has had plenty of time to unwind with his family: Saturday he spent the morning on a private beach with first lady Michelle Obama and their daughters. Then he was off to the golf course in a foursome that included Larry David, the “Curb Your Enthusiasm” comedian.
But he has also involved himself in a long-standing Vineyard political culture that reflects the island’s position as a summer retreat for members of the wealthy liberal elite.
The president’s personal political connection to the island goes back several years. As a fresh-faced potential senator, Obama spoke at a race-relations forum in Edgartown in 2004, and three years later, he returned for a fundraiser in the early stages of his presidential campaign. Several friends – including senior adviser Valerie Jarrett and Charles Ogletree, one of Obama’s former law professors – have summered on the island for many years.
Obama was treading a well-worn path for up-and-coming Democratic politicians in search of support and financing on the island.
For several years, the Democratic Senatorial Campaign Committee has held an annual summer retreat on the island, an invitation-only event for prominent donors to meet candidates seeking their support for the next election cycle. Other political events are lower-key.
On a recent Sunday, a small group of high-profile African American summer residents gathered at the home of Valerie Mosley, a global wealth strategist who was appointed in 2010 to Obama’s board of advisers on historically black colleges and universities.
They were there to listen to Charlotte Golar Richie, who hopes to become Boston’s first black female mayor, speak about her background and why she is running for the job at a fundraiser organized by Ogletree.
Calvin “Kern” Grimes, president of Boston-based Grimes Oil, said that he decided to open his checkbook after listening to her because he thought she was a “qualified candidate” and that “she has to raise a lot of money because the other candidates have a lot already.”
“It was very good, very successful,” he added. “She raised a lot of money”.
Grimes and radio executive Skip Finley said small-scale political fundraisers are very common on the island.
“Some [are] to raise a little money, some a lot of money,” Finley said, “but always to connect with tastemakers, new and early adopters, to gauge popularity in intimate settings and often to get there before [rivals] thinking of running for whatever slot.”
As for the island’s attraction to the rich and powerful, Finley said it was refreshingly egalitarian: “No one expects you to shave or iron your clothes. You can leave a lot of that kind of thing back over there in America, as we say.
“Folks will nod in acknowledging or recognizing you but otherwise leave you alone.”