Editor’s Note: Oak Bluffs author Thomas Dresser’s book, African Americans on Martha’s Vineyard from Enslavement to Presidential Visit, was published on July 4 this summer and is already in its second printing. The book is on sale at outlets across the Island. What follows is an edited excerpt from the chapter titled Mr. President. It appears with permission.


In the late summer of 2004, Barack Obama, a candidate for the United States Senate from Illinois, agreed to participate in a forum on race relations held at the Old Whaling Church in Edgartown, moderated by his former Harvard professor, Charles Ogletree. The forum is held annually on the Vineyard to promote a deeper understanding of the relations that have evolved between the races. This year, the enticement was Mr. Obama, who had just delivered the ringing keynote speech at the Democratic National Convention in Boston the month before.

Mr. Obama presented himself in a casual demeanor but . . . it was a rousing speech. “If we deal with race in isolation, to the exclusion of jobs or the health crisis, we’ll lose. We need to break out of the either/or mentality,” he said. He closed with the words of the Rev. Martin Luther King Jr.: “Although the arc of the human universe is long, it bends toward justice, but it doesn’t bend by itself.”

The crowd gave him a standing ovation.

Other participants in the forum offered insight and advice on how to advance the cause of racial equity. Prof. Caroline Huxby advocated a goal to excel in science and math, and Dr. Abigail Thernstram suggested that schools must be more proactive. Grassroots mobilization was advanced by Prof. Sheryll Cashin. Prof. Lani Guinier noted that the right to vote is determined by individual states and then echoed Mr. Obama’s comments when she said: “Race is a means for masking class. We use the language of race to avoid what’s happening. We need to learn to talk about race and class in the same sentence, or we will be here fifty years from now talking about the same questions.” More than once the issue of class distinction arose in the discussion of race relations. And just as the issue has to be considered as part of the whole political landscape, the impact of class distinctions figures prominently in a discussion of race relations.

The crowd was energized, enthusiastic and invigorated. So, apparently, was Barack Obama, because he returned to the Vineyard in the summer of 2007 as he was laying the groundwork for his run for the presidency. And one Vineyarder kept a close eye on the future president.

Over three days in the summer of 2007, George Gamble of Oak Bluffs (former owner of Among the Flowers Cafe in Edgartown) ran into the future president. Three times.

On his way home from the beach one sunny afternoon — it was August 29 — George noticed several Secret Service people gathered at Donny Gregory’s bike shop in downtown Oak Bluffs. He suspected they were Secret Service agents because they wore earpieces. George and his daughter in law Kathleen walked into the rental area and heard that Senator Obama was renting bicycles, not just for his family, but for his entire Secret Service contingent.

When the senator offered his credit card, George overheard Mr. Gregory say, “This one’s on me. This is my contribution to your campaign.” Barack’s answer was, “No, you’re a hard-working man, and I cannot accept your offer.” After a few more exchanges, Mr. Gregory accepted his credit card. As Barack turned to leave with his bike, George approached him, shook his hand and wished him well in his bid for the presidency. George was impressed with his firm handshake.

The next day, George was in Edgartown at the stop sign at the corner of Main street and the Edgartown-West Tisbury Road. An “army” of bikers approached, headed into downtown Edgartown, with Barack Obama in the lead. George recognized him immediately, leaned out of his window and greeted him for the second day with a “Hello, Senator.” Barack Obama replied with a friendly, “Hello.”

On day three, Friday, August 31, 2007, George had lunch at Farm Neck. As he was leaving the dining room, Mr. Obama and Vernon Jordan were entering. George held the door for the two men and greeted the senator for the third time in three days. At this point, George began to wonder if Senator Obama recognized him or if Obama might think he was being stalked. Yet these were purely chance encounters.

George recounted his three exchanges with Senator Obama to a neighbor, who was duly impressed by the sightings. She, too, had seen Senator and Michelle Obama. She approached the Secret Service to ask if they would get Michelle’s attention so she could say hello. “Why?” they wanted to know. She explained that she and Michelle had gone to Princeton at the same time and knew each other well, in the small contingent of African American students. The Secret Service either did not believe the neighbor or did not think it warranted disturbing Michelle.

That August proved a busy time for presidential hopefuls on the Vineyard. Mr. Obama held a fundraiser, as did Hillary Clinton, John Edwards and Mitt Romney. There is a lot of summer money on the Vineyard, and presidential candidates want a portion of the pie.

Mr. Obama won the presidential election on Nov. 4, 2008 . . . on the Vineyard, he secured 75 per cent of the total vote, enticing an amazing 82 per cent of the 12,945 registered voters to the polls. Overall, the Vineyard stood solidly behind the new president.

Rumors flew across the wire services and the Internet in the early summer of 2009. The tease was that the first family intended to take a Vineyard vacation. Excitement reached a fever pitch. Whether it was the lure of the land from his previous visits, following in President Clinton’s footsteps, the search for an idyllic Island getaway or the appeal of an African American enclave replete with Harvard professors, prominent people and a trio of golf courses, the Obamas chose Martha’s Vineyard for their first family vacation as the first family.

. . . The Obamas arrived in a hurricane and left in a storm; it was quite a week. Hurricane Bill — the storm, not the former president — hovered off the Maine coast as Air Force One landed at the Cape Cod Coast Guard Station. The Obamas were transported to the Martha’s Vineyard Airport by helicopter on Sunday afternoon, August 23, 2009. A number of hardy locals lined the street waving and cheering the president’s arrival; one welcoming sign read, “Obama, take a deep breath and relax.”

That was the intent. On Monday, he played tennis with Michelle and a round of golf at Farm Neck and dined with advisor Valerie Jarrett. On Tuesday, he ventured off to Mink Meadows and played nine holes of golf. At lunch on Tuesday, Mr. Obama was spotted at Nancy’s Restaurant in downtown Oak Bluffs, and his order of fried shrimp, calamari, scallops and French fries was posted on Facebook before he could sit down to enjoy the repast at the home of Valerie Jarrett on East Chop.

Once again, serendipitous cyclist George Gamble was on the scene. He heard the rumor that President Obama’s motorcycle was heading to East Chop. Curious, George hopped on his bike and, using knowledge of the back roads, found the home where the president had gone with his party. The Secret Service kept George at a safe distance, and he struck up a conversation with other onlookers. Although he didn’t actually see the president, he considers this his fourth Obama encounter.

On Wednesday morning at 2 a.m., the president was awakened and informed that Sen. Ted Kennedy had died Tuesday night. The weather precluded any attempt at golf or a public outing that day, and the First Family stayed close to home.

Thursday, August 27, the sun was out . . . after a number of false starts, the Obamas were spotted biking in Aquinnah. The First Family toured the Gay Head Lighthouse and agreed to be photographed with the lighthouse keeper’s wife. President Obama managed to squeeze in another round of golf, this time at Vineyard Golf Club. It was noted in the New York Times that the president was casual in his game, and aides were reluctant to reveal his scores.

The Gazette offered a word of caution: “Presidents deserve some quality time away from the pressure of the office and it is to be hoped the Vineyard offers at least a few true vacation interludes between interruptions.”

President and Mrs. Obama flew to Boston Friday evening, August 28, to avoid Hurricane Danny and prepare for the funeral of Senator Kennedy. Mr. Obama delivered a ringing eulogy at the packed service Saturday morning, then returned to the Vineyard Saturday afternoon.

And then it was Sunday, August 30. With niece Suhalia Ng and Sasha and Malia, Mr. Obama made a quick trip to Alley’s General Store and Garcia’s to stock up on candy, gum, and oatmeal cookies. They boarded the helicopter and lifted off from the Martha’s Vineyard Airport at 4:23 p.m., Sunday afternoon. It had been a whirlwind week for the first African American president.