Hillary Clinton’s Westport Lover

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.

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.

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 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

The story on Hillary Clinton’s romance with David Rupert was overshadowed by Globe stories about Paul McCartney, Jackie Onassis, even Annette Funicello.


Click here for “06880+”: The easy way to publicize upcoming events, sell items, find or advertise your service, ask questions, etc. It’s the “06880” community bulletin board!

33 responses to “Hillary Clinton’s Westport Lover

  1. Wow – “I own a house that someone who dated Hilary Clinton slept in.” Wonder if that increases the property value?

  2. Now this is a house that needs to be preserved for future generations. Dan – could you connect Mr Schachter with Morley Boyd to get the preservation/deed restrictions process started.

  3. I would just be happy if the property value might not decrease
    Here slept a pathological liar and a woman who defended a sexual predator

  4. We were friends and neighbors of David and his wife Judy O’Brien. We attended his memorial service after his untimely death. Arriving late, we were seated near the back of the church. Just as the doors were closing, Hilary Clinton, then Secretary of State, slipped in and sat in the back row. Just before the service ended, she slipped out. I don’t believe this was ever reported in the press, but my wife and I found it rather touching.

  5. Dan:

    I am truly a big fan. I like a lot of the issues you put in the public area for comments of locals — and a few people who left years ago and need to vent A LOT — but this story of who Hilary slept with 40+ years ago is just caca.

    If every politician knows that every aspect of their lives will be exposed, from the time they cheated on a 4th grade spelling test to their first love affairs, no one will go into the profession.

    It’s bad enough that either the power positions corrupt or sleezy people are attracted to the profession, but we get what we get.

    I personally have many, many issues with Hilary Clinton, but I find the alternative scarier. And I don’t care about her sex live at all. And her sex life 40+ years ago is not an important issue at this juncture of America’s political future. It muddies the water for no added value.

    I know this town is crazy to make Westport connections for every issue on the planet, but really….on a slow news day, please do the CAN YOU BELIEVE HOW THIS GUY PARKED pictures. This is not worthy of you.

    Stephanie Bass

    • Yet earlier this year you thought a 10 year old story about a random encounter with Trump was worth commenting on – and not with the same “why does it matter” attitude? Hmmmm.

      • Couldn’t agree with you more Jerry. Let’s treat this story for what it is– an interesting tie-in between a candidate running for the highest office in the US and her former ‘first true love’ who resided in Westport for many years. And……… the fact that tabloids covered this in 1999 after the book about Hillary came out makes it good for a few laughs. Let’s lighten up a little………. as one comment suggested- nobody was ‘outed’ here–

  6. It’s difficult for me to believe that this article from the past deserves merit.
    So what’s next? Details about “Jackie O Branded A Thief!
    Let’s make an effort to raise the bar in this particularly unique political time.

    • Chillax people. Dan posts all sorts of things that have relatively tenuous connections to Westport, many of which fall into the “I wouldn’t die unfulfilled if I hadn’t read that” category but also in the “isn’t that interesting” category. This is just one more in a long history of posts.

      It’s not like Dan is “outing” Hillary. It’s not a secret that she had a relationship with Mr Rupert. It was in a book. It’s been reported on before. As best I can tell, a great many northeast college kids were engaged in similar activities in the late 60’s so there is little shock value for anyone, least of all sophisticated Westporters.

  7. Dan:

    Are we allowed to call each other assholes on this site?

  8. Stephanie…are you volunteering?

  9. Nancy Hunter Wilson

    Dan, did you ever consider that this juvenile post could be read by the Rupert family? What do you gain? You’re a smart guy from a smart college. How does your team deal with their coach sending this crap out into the “world”?

    I’ve never been so disappointed.

  10. Looks to me like there’s a lot of “I’m with her” thin skins here. Read today the press has been pressured by her campaign to lay off her health issues. Hmmm…I also saw that “Hillary’s Health Concerns Serious, Say Most (71%) Doctors Polled by the Association of American Physicians and Surgeons (AAPS)”….Hmmm wonder what’s up with that?

    • Peter Gambaccini

      What’s up with that is that the AAPS is known to be a politically conservative organization and that 71 percent figure does not represent all American physicians. In other words, that entire story is bogus.

      • The Association of American Physicians and Surgeons – AAPS – is a non-partisan professional association of physicians in all types of practices and specialties across the country.

        Since 1943, AAPS has been dedicated to the highest ethical standards of the Oath of Hippocrates and to preserving the sanctity of the patient-physician relationship and the practice of private medicine.

        Our motto, “omnia pro aegroto” means “all for the patient.”

  11. Bonnie Bradley

    Wow! Ease up guys. Dan is a really nice & kind person. We all have our quirky moments….. Give him a pass on this one.

  12. Hi Dan-

    Thank you for another interesting story about a person we all know with a Westport connection.

    Too bad that preconceived notions ( right and left ) color the way this story is seen and set you up as a target.

  13. Dan, Lad….you keep it up. Your blog is terrific. People today seem to be over the top politically correct. The world is as it is….let’s enjoy the entertainment value of your topics and resultant comments…I love it.

  14. Since this concerns someone who could be (and in this case is uniquely qualified to be) the President of the United States it seems a demeaning and juvenile post. Like all women in our society Hilary Clinton deserves to be treated with dignity. Measure this story on the standard of how blog worthy each of our intimate relationships would be. Measure it on the embarrassment such an invasion into a relationship would cause. So what if tabloid media had the story. Why add to the filth generated by an incompetent media manipulated by one the grossest, most corrupt monstrosities our declining culture has spawned?
    ( I guess I didn’t hold anything back on that one.)

  15. Mary (Cookman) Schmerker Staples 1958

    Dan, I find your reporting very interesting. All you did was report on an interesting historical note. Others are the ones who have turned the post into a political heyday. As far back as I can remember people were still talking about where George Washington ate and slept and it was reported that he probably ate a meal in a tavern in Westport. So, thank you for reporting on this footnote to history.

  16. Maybe the house should be added to the Jennings Trail?
    Lighten up everybody. Thanks Dan, always something interesting on 06880 and I also know I don’t have to read the ones I’m that do not interest me!

  17. Just saying, I think this post is interesting information and has that “where Westport meets the world” flavor to it. I’m always fascinated how Dan weaves interesting connections of world events including this crazy election time and somehow, just somehow comes up with a connection to Westport. Plenty of info (good and bad) out in cyberspace on both candidates — who Hillary’s boyfriend was in college is hardly racy information – anyone remembering their college years can relate to a passionate, hormonal love affair I would hope. Just an interesting connection imho especially with a photo of the house. I’m sure Dan’s kids think he’s very cool.