Lunch With Ambassador John Loeb

Diane Clehane & John Loeb

Despite the dreary weather (Will spring ever stick around?), I made my way to Michael’s yesterday to check in with the power lunch crowd. Now that I’m doing the column twice a month, I really look forward to my Wednesday visits to 55th and Fifth. This week, I was thrilled to bump into an old friend – and former boss – Laurel Touby who I met in this very dining room 13 (!!) years ago. At the time, Laurel was running Mediabistro, the popular media-centric site she founded which besides curating and covering news on the business of media, ran a lucrative job search arm of the site, offered courses and held events for aspiring media-ites at a time when it was becoming clear the future was digital. Brilliant Laurel later sold mediabistro to Jupiter Media for $23 million. Since then, she has been focused on investing in emerging technologies and talent. She is one of the smartest women I’ve ever met, and I’ll always be grateful to her for introducing me to the Michael’s crowd.

Before we made our way to our respective tables, we chatted for a few minutes with another Michael’s regular, Michael Gross, mostly recently EIC of Avenue magazine, who has now decamped back to familiar stomping grounds. Michael told me he is hard at work on another book but told me its subject is top secret. For now. Stay tuned!

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I was looking forward to this week’s lunch with Ambassador John Loeb and was more than a little intrigued when, ahead of our date, his new book, Reflections, Memories, and Confessions, arrived at my house last week. Besides its considerable heft – I kid you not, the book weighs six pounds – it is a stunning chronicle and something of a personal scrapbook of an extraordinary American life. In the course of the hundreds of interviews I’ve conducted over lunch at Michael’s, I’ve met plenty of people whose lives were worthy of the big screen treatment, but Ambassador Loeb’s story would make a riveting mini-series. Think Winds of War or Rich Man, Poor Man – although the ambassador’s version might be called Rich Man, Richer Man.

How did Loeb turn out such a heavy (literally!) body of work? “I spent 20 years thinking about it – stopping and starting with it,” the ambassador told me when he joined me and his publicist, media maven Judy Twersky, at my usual perch (Table 27). “Then, I spent two years very focused on writing it at home in Purchase [in Westchester County].”

The charming and dapper ambassador, who turns 89 years young today, descended from the founders of two major Wall Street firms, Lehman Brothers and Loeb, Rhoades. Having lived in New York City for most of his life (he told me he had just sold his Upper East Side residence on this very day). Loeb now spends most of his time at his estate in Westchester County where he lives with his wife, Sharon, and works from his home office with a small staff (of three!) assisting him with his business interests (including a vineyard and licensed wine business), philanthropic works and engagements (Loeb will be speaking at the University Club on June 11th and in Newport, Rhode Island at Touro Synagogue on August 18th).

Loeb’s parents were John L. Loeb Sr. who the New York Times called a “pillar of Wall Street” and Frances Loeb née Lehman of the Lehman Brothers dynasty. His grandfather, Carl Morris Loeb, a Jewish immigrant from Germany, founded Carl M. Loeb & Co. which became Loeb, Rhoades & Co., one of the largest and most powerful investment banking houses of the twentieth century.

His family’s fascinating history along with Loeb’s reflections on the power, prestige, and privilege which defined his life – and spurred a lifetime commitment to public service and civic responsibility is chronicled in the over 700-page book. (I usually read an author’s book before interviewing them, but I confess, this time I skimmed it.) I was surprised to find as much as personal anecdotes about the ambassador’s family life as I did in the book. Loeb talks candidly about his wives – most notably his current wife and great love, Sharon Handler, an international attorney, who he married in 2013. He also devotes a chapter to his daughter, Alexandra Driscoll, and his son, Nicholas Loeb, honestly depicting the ups and downs of a father-son relationship. I was surprised to discover Nicholas was the man I knew best from Page Six, who in recent years has made headlines for his contentious relationship with his former fiancée, actress Sofia Vergara.

Loeb’s early years are also covered in great detail in the book (which is available on Amazon – there’s also an ebook). He attended Hotchkiss (which he hated) and Harvard (which he loved) and paints a compelling picture of growing up within those privileged environments while battling the ugliness of anti-Semitism. The ambassador told me stories of growing up in Greenwich, Connecticut where neighbors “had to commit not to sell their house to Jews.” Of his college years, he said, “At the time, Harvard had many clubs that would not take Jews, now my nephew is Porcellian [The university’s final all-male club], and the president is black.” Loeb’s own experiences with anti-Semitism has spurred on much of his charitable work — all written about extensively in the memoir.

In asking questions about Loeb’s impressive tome, it was hard to know where to begin, so I was glad when the ambassador began to tell the story behind the photograph that appeared to be taken outside of Buckingham Palace that appears on the endpapers of the book. “It was taken in 1949 when my family was invited for tea,” he explained as he sipped his pea soup. “The Loeb Rhoades office had stayed open in England during the war,” he said, and because of that, the British government – and the Royals wanted to express their appreciation. That invitation opened the door to a whole new social circle to the young Loeb. “There weren’t a lot of single men my age after the war, so I became very popular – especially during ‘the season,’” he laughed. “I started to get invited to ‘deb parties’ which were not just attended by young women, but everyone from great grandparents to young children. I met a lot of people.”

At another such party in 1953 at the ancestral home of the Duke of Wellington, the Loeb had “one of the greatest encounters of my life” when he met Winston Churchill. “I saw this man and thought, ‘He looks a lot like Churchill.’ I went over to introduce myself, but he said nothing. I talked to him, but he just looked at me and smiled.” The revered prime minister may have wanted to chat if he’d only known what an influential role, he would wind up playing Loeb’s life.

The book is filled with incredible stories populated by the many of the world’s most famous and influential people including plenty of tales about Loeb’s relationships with many US presidents and politicians including Ronald Reagan subsequently appointed Loeb US Ambassador to Denmark. During his tenure as ambassador, Danish popular support for NATO reached unprecedented levels, and Queen Margrethe II presented him with the Grand Cross of the Order of the Dannebrog in recognition of his diplomacy. There’s plenty for royal watchers to pore over in the book’s pages, too.

Having been raised to believe that a full life is equal parts education, work, and philanthropy, Loeb inherited the legacy of the Winston Churchill Foundation, founded in 1960, from his father (which was born out of his friendship with Lew Douglas, a former US ambassador to the Court of St. James). The foundation was created in support of Churchill College in Cambridge, England, which was, said Loeb, “The MIT of England.” Loeb had just completed his assignment as ambassador to Denmark in the mid-eighties when Loeb’s father gave him a specific task, “My father said, ‘You love England, so you’re job is to raise money.” He did so splendidly by creating the Winston Churchill Award working with the foundation’s executive director Harold Epstein. “They were down to their last $400,000.” Imagine that. By tapping into his considerable skills of persuasion, not to mention impressive contacts, Loeb managed to raise $2.3 million in short order by honoring a roster of leaders including Margaret Thatcher and H. Ross Perot (who received the award from Prince Charles). How’s that for name-dropping?

Knowing that we shared a love of all things British, I told the ambassador I loved the passage about his 75th birthday party thrown by his then-girlfriend Sharon, at Blenheim Palace, a stunning country house in Blenheim, Oxfordshire, England in 2005. It was the hottest ticket among a certain circle of New Yorkers at the time. Among the attendees: Anne Hearst, Beth DeWoody, Susan Fales-Hill, Mary McFadden, and Kip Forbes. You get the picture. “Everyone was expecting me to propose,” said Loeb smiling at the memory. “And was upset I didn’t, but I did eventually.”

Tucked among all the incredible stories about his life and career, I found his anecdote about meeting the daughters of Janet Bouvier Auchincloss quite funny. In 1951, young Loeb was staying in Madrid with a poor family “and desperate for a pool” when a certain marquis had promised Janet he would introduce her daughters (who were touring Europe that summer) to a bullfighter. When none were to be found, he convinced twenty-year-old Loeb to dress and play the part. “I remember when I arrived Jackie and Lee were slightly inebriated.” The ruse seemed to work –until the next day when the young women invited the faux matador to lunch at the Ritz. “I told them the truth, and they were furious,” Loeb told me. “Years later Letitia Baldridge [Jackie’s social secretary in the White House] said Jackie thought it was funny, but I don’t think she did.”

Lunch at Michael’s

Seen & Heard Around the Room

Michael Waisman on Table One … Interior Design guru Ryan Korban on Two … Andrew Stein and an attractive blonde we didn’t recognize on Three … G III’s Morris Goldfarb on Four … Allen & Company’s Stan Shuman on Five … Hail, hail, the gang’s all here: Dr. Gerald Imber, Jerry Della Femina, Jeff Greenfield, Andy Bergman and Michael Kramer back at their regular perch on Table Six … Paige Peterson on Seven … New York Social Diary’s David Patrick Columbia and Brooke Hayward on Eight … Suzy Halpin on Nine … Security expert and tv talking head Bill Stanton on Ten.

Moving On

MediaVillage founder Jack Myers on Table Twelve … David Slackman on Sixteen … David Poltrack on Eighteen … Producers Joan Gelman and Sandy Pearl on Twenty … Quest’s Chris Meigher and Michael Gross on Twenty-one … Gilt’s Kevin Ryan on Twenty-two … Fashionista blogger Sydney Sadick and her mom (who we thought was her sister!) Amy Kamin on Twenty-six … Laurel Touby and author/investor Zackary Karabell on Twenty-nine.

I’ll be back at Michael’s on May 15th to dine and dish. See you then!

Diane Clehane

Diane Clehane is a leading authority on celebrity and royalty who has written for Vanity Fair, People, and many other national outlets. She is a New York Times best-selling author of five books, including Diana: The Secrets of Her Style and Imagining Diana. She appears regularly on CNN.

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