Six years ago — shortly after Seth Schachter moved to Westport — someone knocked on his door.
The daughter of an elderly neighbor across the street did not offer a welcoming apple pie. Instead she asked, “Do you know who lived in your house?”
Seth had no idea. She said she’d be back in a few minutes.
The neighbor’s daughter returned with a copy of a 1999 Globe story. (The supermarket tabloid, not the well-regarded Boston newspaper.) It showed a photo of Schachter’s new house — next to the White House.
Globe photos of David Rupert’s house, and Hillary’s.
Turns out that 17 years ago, Gail Sheehy wrote Hillary’s Choice. The biography of the then-First Lady included an account of the “tempestuous” relationship between Wellesley College student Hillary Rodham and David Rupert, a government major at Georgetown University (where, coincidentally, a classmate was Bill Clinton — who had not yet met his future wife). Rupert and Hillary met when she spent her junior summer in Washington.
After the book came out, reporters hoping for more scrambled to find the First Lady’s former boyfriend. They found him on Rustic Lane, off Greens Farms Road — in the house Schachter now owns.
The reason Rupert was such a catch — and why satellite trucks raced to Westport — was because of Sheehy’s provocative writing. She said that Hillary kept the relationship “secret from some of the people in her life.”
She added: “Rupert was every bit as abrasive and competitive as Rodham.” But “he liked her spunk.”
David Rupert and Hillary Clinton, while they were dating. The Globe called him a “Jim Carrey look-alike.”
By 1969, Sheehy wrote, their long-distance relationship was suffering. However, Rupert “discovered something unexpected about Hillary: get her away on a weekend, and she could be playful.” (He did not tell Sheehy whether his girlfriend “inhaled,” but urged the author to “read between the lines.”)
Rupert felt he was Hillary’s “first true love.” In another book — Bill and Hillary: The Politics of the Personal, author William H. Chafe calls Rupert “her second serious boyfriend.”
And the Globe story quotes a neighbor of Rupert’s — presumably from Westport — as saying, “He was the man who made a woman out of Hillary.”
As a student at Yale Law School, Hillary made weekend trips to Bennington, Vermont, where Rupert had moved. But their differences grew, as neither was willing to relocate to accommodate the other.
In the Globe‘s words, “they would argue about politics, the Vietnam War — and make up with passionate love.”
Rupert and Hillary dated for almost 3 years. Her college friend Nancy Pietrafesa told Chafe, “they had an intense love affair.”
In the final stages of their relationship, Rupert told Sheehy, “I never stated a burning desire to be President of the United States. I believe that was a need for her in a partner.”
David Rupert, around 1999.
Instead, he headed toward the non-profit sector — “all very noble, but not where Hillary wanted to go.” He earned a master’s degree in management — from Yale, ironically — and became an executive with both public and private organizations.
(The Globe story called Rupert “pretty darn successful himself … happily married and living in a $500,000 house in Westport, Connecticut.”)
Back then, Rupert knew of Hillary’s relationship with fellow Yale Law student Bill Clinton. In fact, they started going out while she was still dating Rupert. “If you care for him, then go for it,” her boyfriend told her about Clinton.
Which brings us back — almost 30 years after they split — to the 1999 Globe coverage. A headline teased “Hillary’s Affair with Jim Carrey Look-alike.” The story compared Rupert’s Rustic Lane house with hers — at 1600 Pennsylvania Avenue.
The full Globe story, with all its details.
The Globe noted that when Chelsea Clinton discovered a photo of Rupert in her mother’s album, Hillary called him “a very special friend from a lot of years ago.”
I knew David Rupert. I spoke with him a few times about his brush with fame. Mostly, he was amused. I pressed him for details about his former girlfriend, but he kept mum.
He lived long enough to see her become not only First Lady, but also senator from New York and Secretary of State.
But he did not live to see Hillary Rodham Clinton become the 1st woman nominated by a major party to run for president of the United States. (And, no doubt, for Rupert himself to be rediscovered by the media). He died in May of 2009, at 61.
Which makes Seth Schachter’s Westport house just a minor — but very intriguing — footnote to American history.
The story on Hillary Clinton’s romance with David Rupert was overshadowed by Globe stories about Paul McCartney, Jackie Onassis, even Annette Funicello.
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