Frank’s First Ladies: Sinatra & Jackie, Nancy, & Eleanor

Eleanor Roosevelt and Frank Sinatra at a 1947 Democratic Party fundraiser where he shows off a statue of FDR and then a decade later. She also appeared on his television show.

He started as an avid Democrat and ended as an active supporter of Republicans and through those ensuing decades the legendary entertainer Frank Sinatra befriended three very different women who happened to be married to Presidents.

The Reagans enter the 1981 Inaugural Gala with Sinatra.

The Reagans enter the 1981 Inaugural Gala with Sinatra.

Reagan cuts in on Nancy and Sinatra dancing at his birthday party.

Reagan cuts in on Nancy and Sinatra dancing at his birthday party.

The most recent of the trio was Nancy Reagan. And while some thought their friendship was often flirtatious, the truth was they shared many common friends in the entertainment industry and had both been long-term residents of Los Angeles, where the singer-actor had initially met the Reagans.

Just as he had for Jack Kennedy, Sinatra produced Ronald Reagan’s 1981 Inaugural Gala and included a special song, Nancy with the Smiling Face. 

Nancy Reagan singing the original song To Love a Chold with Frank Sinatra at the book'launch party on the White House lawn

Nancy Reagan singing the original song To Love a Chold with Frank Sinatra at the book’launch party on the White House lawn

Sinatra was a guest at the surprise 71st birthday she hosted for the President, his first in the White House, a month later.

There’s a famous picture of Reagan cutting-in on Nancy and Sinatra dancing.

A year later, Sinatra was back and performed with Nancy, both singing the song, To Love a Child, in an events tent on the White House lawn, written especially for the event, a kickoff for a new book the First Lady wrote the introduction to by the same name, part of an effort to help the Foster Grandparents program.

It wasn’t until after John F Kennedy was elected president in 1960, avidly supported by Sinatra who made the first conscious effort to enlist famous Hollywood names in support of a presidential candidate, that Jacqueline Kennedy first came to know him.

Sinatra escorts Jackie Kennedy to the 1961 Inaugural Gala he produced and then again in 1977 to an Italian restaurant in New York after she attended his concert.

Sinatra escorts Jackie Kennedy to the 1961 Inaugural Gala he produced and then again in 1978 to an Italian restaurant in New York after she attended his concert.

While a photograph of him escorting her into the 1961 Inaugural Gala, which he produced, became so widely circulated that it seemed like they were practically intimates, the suggestion of a chummy dynamic was misleading.

In fact, during a formal luncheon held in the first year of the Kennedy Administration, the First Lady was distressed to learn that Sinatra had wangled a way into the event as if it were a hotel fundraiser rather than an invitation-only honor.

The degree to which Sinatra was or was not involved in abetting the President’s extramarital affairs remains a matter of speculation, lacking any firm documentation which proves or disproves it entirely, but whatever Jackie Kennedy might have thought about this – or whether she even heard about it or believed it is a matter of pure conjecture.

Born in 1929, however, Jackie Kennedy was born into that bobby-soxer generation of young women who swooned over “Frankie Boy” in the Forties and a strong suggestion that she, at the least, loved his music was proven in October of 1978.

Marking her independence in a way she never before had as a public figure, the by-then Jackie Onassis was employed in her first salaried job in 22 years, as a book publisher editor.

While it was ostensibly to lure Sinatra into inking a deal with her as editor to write his memoirs (which didn’t happen), the real excitement for the former First Lady that night was to escorted by the star to his own concert, at Madison Square Garden.

After the show (she went to a second performance later that week), the two famous faces were snapped alongside one another by a pack of paps as they made their way into an Italian restaurant, joined by several Sinatra associates and actress Jane Fonda.

During their night out on the town in 1977, Jackie Onassis and Sinatra were joined by Jane Fonda who crammed into the car with them.

During their night out on the town in 1978, Jackie Onassis and Sinatra were joined by Jane Fonda who crammed into the car with them.

To what degree they might have remained in touch is unclear, but the efforts of gossip columnists failed to convince anyone there was a romance developing.

When Sinatra learned with the rest of the world that the former First Lady was battling cancer in the winter of 1994, he sent her massive flower bouquets and encouraging notes, hailing her as “America’s Queen.”

If there was a touch of flirtation to the friendship Sinatra enjoyed with Nancy Reagan and Jackie Onassis, his relationship with the older Eleanor Roosevelt was a sort of motherly reverence.

Sinatra had first become drawn into politics as an avowed supporter of President Franklin D. Roosevelt, and actively campaigned for the incumbent Chief Executive for his third term, in 1940. In truth, however, his personal convictions on civil rights were more closely aligned with the more liberal First Lady.

Following FDR’s death, Sinatra drew especially close to Eleanor Roosevelt, displaying not only an awed admiration for her personally but hailing her for drafting the Declaration of Human Rights while she worked as an American representative at the newly-formed United Nations..

A tactical and savvy politician who became even more politically overt after she left the U.N. during the Eisenhower Fifties, Eleanor Roosevelt was nevertheless not immune to Sinatra’s charm.

Eleanor Roosevelt talk-singing with Sinatra on TV, 1960.

Eleanor Roosevelt talk-singing with Sinatra on TV, 1960. (

So much so that she agreed to fly cross-country simply to appear with him on a television special in February of 1960. As her public relations representative later recalled of the trip and the taping:

“We arrived in Los Angeles in a cloudburst. An attendant handed me a big umbrella, saying, ‘Will you take care of the little lady?’

Mrs. Roosevelt towered over most people, including me. We both burst out laughing.

Friends met her at the airport and I caught up with her that evening at the studio. She was finished in ten minutes. She had studied her part.

One thing bothered her. She was to walk to a bench on the set on a magnificent white silk panel about twenty yards long. She was worried about soiling it. A production man assured her that it would be thrown away after the show. This offended her sense of thrift. Could she have it? Of course, he said, and it was sent to Hyde Park–for what purpose I couldn’t guess.”

From all accounts, the last time Eleanor Roosevelt and Frank Sinatra were together was in October of 1960, when they made a joint radio appeal on behalf of JFK’s presidential bid.

Here’s a clip of Eleanor Roosevelt on the Frank Sinatra television special. It’s a bit less smooth than the usual sort of performers Sinatra was accustomed to co-starring with, since her “performance” is really a matter of a spoken word exchange, a version popular song “High Hopes” that was more talk than sing:

And here’s a rarely-seen clip of a press conference before a concert fundraiser for Reagan during the 1980 presidential primaries, including entertainer Dean Martin – who almost steals the show, Ronald and Nancy Reagan, Frank Sinatra and his wife Barbara:


Categories: Eleanor Roosevelt, First Ladies, History, Hollywood, The Kennedys

Tags: , , , , , ,

14 replies

  1. Just a small correction: February 6, 1981, Reagan turned 70, not 71.

  2. This is fascinating Carl. Sinatra’s relationships with these women crossed party lines and appears to have been genuine. I don’t think he was an opportunist but rather a sincere liberal at heart with strong beliefs, even later in life when he was friendly with Nancy Reagan. His support of FDR and his later support for Mrs. Roosevelt and her work, and then his support for JFK in 1960 seem to indicate that. I had no idea that he and Jackie had become friendly–and Jane Fonda no less!–I thought when he had the falling out with JFK and RFK that was the end of his association with the Kennedys.

    • Your description is absolutely correct. After Reagan, though Sinatra did organize the 89 Bush Inaugural Gala, he dropped from politics. He did make an appearance at the Clinton White House I seem to recall, but no longer expressed his political views. Thanks for writing.

  3. Okay, I have an odd question: Eleanor Roosevelt was born in New York City… where did her accent come from?

    • Not an odd question at all. Her distinctive voice, similar in accent to that of FDR and her first cousin Alice Roosevelt Longworth, now gone from our collective, contemporary experience, was one which distinctly identified the elite class of the Eastern seaboard well into the llatter mid-20th century. Even Jackie Kennedy and her now-equally well-known cousin Edie Beale had a slighter version of it.

  4. What a great article! I knew some about Sinatra with Jackie and Nancy, but nothing about Eleanor Roosevelt. I also enjoyed seeing the photo of Sinatra, Jackie and Jane Fonda. I had seen the Madison Square Garden photo of just Jackie and Frank before, but not the one of them with Jane. (Could you imagine if there had been a car accident that night with THOSE three in a car together?) As always, informative and entertaining!

    • Not until I found that image did I realize Fonda had gone to the concert too. Perhaps she was at the restaurant and they invited her along to the concert! I’ve a picture or two of Sinatra with Pat Nixon as well in other articles on this website but they were not clhummy as was true with thes e other three relationships. Thank you for writing!

  5. Great piece on Sinatra and the president’s wives. Thanks for liking my post on the mother of invention, at Best of luck with your work.

  6. Great post! If my memory (often faulty) is correct, the song Frank sang for Nancy Reagan was actually “Nancy with the Laughing Face”


  1. Speculating on Presidential Sexuality & the first Lesbian First Lady « Carl Anthony Online
  2. Banned Books That Shaped America: The Adventures of Huckleberry Finn | Waldina

Leave a Reply