Island author, Pulitzer-prize winner and self-described “deep-green, feminist, tree-hugging” Geraldine Brooks recalled a thankless trudge through New Hampshire canvassing for then-Senator Barack Obama in 2007. Retreating to a diner on that frigid day Ms. Brooks ventured to canvass the dining patrons as well.

“As I approached a friendly-looking couple, I noticed that they, too, had clipboards,” Ms. Brooks said. “The cafe was filled with fellow Obama volunteers, except for one guy. He turned out to be canvassing for Edwards.”

The remarks kicked off an evening at the Union Chapel on Thursday with a roster of prominent Vineyard Democrats who had gathered for a special fundraiser. The evening began at roughly the same time the President was landing on the Vineyard to begin a 10-day family summer vacation.

Titled Voices for Obama, the fund-raiser, which started at $100 a ticket, featured 10 writers with Vineyard connections who spoke about the President in a variety of literary and lyrical styles.

men talking Greg Craig
Former White House Counsel Greg Craig lent his voice. — Jeanna Shepard

Former White House counsel Greg Craig offered a lawyerly critique of the Republican congressional agenda and strategy, calling GOP Rep. Paul Ryan’s budget plan “a silly and cruel piece of legislation” and the debt ceiling showdown “a manmade economic crisis” designed to humiliate the President.

Alan Dershowitz, who confessed that it was the first time he had set foot in the Union Chapel in his 22 years on the Vineyard, pledged to avoid controversy.

“[Event organizer Tom Lesser] asked me to please not say anything controversial about Obama,” he said. “All right, good night.”

Mr. Dershowitz instead chose to speak about the prospect of Supreme Court openings. He pointed out that four of the justices will be aged 83, 80, 79 and 77 by the end of the next Presidential term.

“We all prefer that the next four vacancies on the Supreme Court be filled by Barack Obama than by any Republican candidate,” Mr. Dershowitz said. “Is there any controversy about that? . . . We have a job. We have to go out and persuade the American people how important the Supreme Court is to the future of the country.”

neck tie suit eye glasses man talking Alan Dershowitz
Pictures by Alan Dershowitz spoke about Supreme Court. — Jeanna Shepard

Harvard Law Prof. Charles Ogletree, who mentored the former Harvard Law Review president in the 1980s, recalled a meeting with the future president when he was at a crossroads in his young career.

“‘Tree,’ as he called me, he said, ‘I don’t know, I’m the president of the Harvard Law Review so you know I could clerk for the Supreme Court. I’m one of the top students in my class academically, I can earn $100,000 a year in salary, but I told the people of Chicago that if I got my law degree from Harvard University I would come back and continue to be a community organizer.’ He said, ‘Can I give up $100,000 and the supreme court clerkship and go back and serve Chicago as I want to do?’ And I said, ‘Barack, yes you can. And Barack hasn’t given me one ounce of credit for it.”

Mr. Ogletree won easy applause from the audience by asserting that the President had married up with First Lady Michelle. He also acknowledged the sour political mood of the country.

“I know everybody’s upset about something,” he said. “We all want to say we think we could have done it differently. . . Really? With this congress? I say give the brother a break.”

Author Richard North Patterson began his talk with something of a stand-up routine, ripping off a number of memorable one-liners, including the claim that Mitt Romney has more positions than the Kama Sutra.

“We’re gathered here on Martha’s Vineyard, also known as the heartland of America,” he said. “After all this is the Island where according to the great historian Michele Bachmann Paul Revere rode to warn that the British were about to abolish marriage between a man and a woman.”

But his talk quickly turned serious.

“We risk becoming a country in full flight from reality,” Mr. North Patterson said before laying out the case for Mr. Obama.

“He stopped the recession, stopped don’t ask don’t tell, saved the auto industry, tackled the tragic anomalies of health care, got Bin Laden, helped enact financial reform, began withdrawing from Iraq and importantly restored the badly-eroded respect for our country around the globe. More remarkably, he did this despite obstruction from a right-wing bent on his destruction even if it meant destroying their own country and the carping, unfortunately, of a left-wing that too often imagines, like a child waiting for the tooth fairy, that he can give them everything they want simply by willing the creation of some liberal nirvana.”

Rose Styron and her daughter, Alexandra, both spoke, the latter reading an essay by her father, author William Styron, about dissolving racism in late-night bull sessions with fellow author James Baldwin. Mr. Baldwin was the grandson of slaves, Mr. Styron of slave owners.

Other speakers included prochoice activist and obstetrician Ken Edelin, who read a Twas’ the Night Before Christmas-metered hagiography of the President that he had penned, while Kate Taylor sang a tune she had written after the inauguration.

Headlining the event and speaking last was Democratic National Committee chairman and Florida Cong. Debbie Wasserman Schultz, who stayed firmly on message in her address to the expectant crowd about the year ahead.

“It’s going to be incredibly important that we all spend the next 15 months living, sleeping and breathing making sure that everyone in America understands the direction that [the President] is trying to take us and the consequences for making the wrong decision,” she said.