Frank Sinatra's copy of the deluxe limited edition of the 1961 official program of the inaugural ceremonies for President John F. Kennedy and Vice President Lyndon B. Johnson.

What you see: Frank Sinatra’s copy of the deluxe limited edition of the 1961 official program of the inaugural ceremonies for President John F. Kennedy and Vice President Lyndon B. Johnson. Sotheby’s estimates it at $3,000 to $5,000.

The expert: Selby Kiffer, senior vice president and international senior books specialist for Sotheby’s New York.

What is this deluxe limited edition 1961 inaugural program worth without the Sinatra provenance? It’s probably something like $700 to $1,000, but maybe that’s a bit aggressive–$600 to $800 for a deluxe limited edition that went to no one of consequence except being a big donor.

How big was the press run? When they don’t state a limitation, my assumption is it’s fairly high. Checking results at auction, the highest-number copy was in the 700s. If I had to speculate, I’d say 1,000 [were printed].

How often does the deluxe limited edition 1961 inaugural program come to auction? Every couple of seasons, but it could come up at sales of political memorabilia, which is a separate area [from books and manuscripts]. There’s probably one available every 18 months.

What makes this version deluxe? The standard version would have been what you or I could obtain if we attended the Kennedy inaugural in 1961. This was made for presentation for donors to the inaugural event, which Sinatra certainly was, or to donors to the Kennedy-Johnson campaign. This was for VIPs, essentially.

How did Kennedy and Sinatra become friends? I don’t know that it’s known when they met, but it’s generally acknowledged that they met through Peter Lawford, being the senator’s brother-in-law and an associate member of the Rat Pack. Both were stars: Sinatra in entertainment, and Kennedy a rising star in politics. Both were charismatic, and both were the sort of people other people want to be around. There was mutual admiration. Sinatra was a New Deal FDR Democrat. He was probably excited to see a younger version of that.

Seems that Sinatra went all-in on Kennedy. He retooled High Hopes as a campaign song… I think Sammy Cahn wrote new lyrics for High Hopes as a campaign song. I think Sinatra saw a winner in Kennedy. He wanted to associate with that, and he believed in him. I think he felt he was a better choice for the country and he tried to convey that through campaigning. Sinatra had several peaks in his career. He could have made a lot of money singing anywhere, and he spent some of those nights on campaign appearances.

Does the 1961 inauguration of Kennedy represent the peak of the Kennedy-Sinatra friendship? I think it has to, because the inaugural balls, the entertainment, Sinatra was put in charge of that. He chose not to treat that as an honorary position. He worked the telephone, strong-armed people, and turned out an amazing cavalcade of stars to perform. The president thanked him for his work. It had to be the pinnacle for Sinatra [who probably thought]: “I helped put him in the White House, and he acknowledged me.”

Can you talk about how their relationship ended? Sinatra, for all his charisma and bravado and his tough-guy exterior, did not like to be disappointed. He anticipated hosting President Kennedy, as he had hosted Senator Kennedy, at his Palm Springs estate in 1962. At the last minute, after making lots of preparations for Kennedy and the Secret Service to be there, he was informed that Kennedy would not stay at his property, but would stay with Bing Crosby instead. It was particularly irksome because Crosby was a Republican.

Why would Kennedy have chosen to stay with a Republican rather than another prominent Democrat in Palm Springs? Crosby may have been seen as safer than Sinatra, who was seen as a bad boy, and who was in the tabloids in a way that Crosby was not. The association [with Sinatra] could prove embarrassing in a way that associating with Crosby would not be.

The end of the friendship is tragic, but I don’t see how it could have been avoided. Kennedy had chosen his brother, Bobby, for attorney general, and was rightly getting heat for that, even though Bobby proved capable. One of Bobby’s main tasks was targeting the mob, and if Sinatra didn’t have mob ties, many believed he had them… This is pure speculation, but maybe Kennedy tried to get a message to Sinatra to the effect of “Look, if it was solely my choice, I’d be with you, but I’ve been advised I can’t do that.” It’s speculation that the president tried to explain it that way. I think it stung Sinatra very deeply. I do think he came to realize that President Kennedy didn’t really have an open choice to stay with him.

Sinatra was clearly hurt by the snub, but he hung onto this program and he mourned Kennedy’s death, even though he went on to campaign for Republicans… People do change their politics. Sinatra did campaign for Ronald Reagan, who was also a former New Deal FDR Democrat. I think that progression–as people get older, the move from one party to another is not unusual. It could be his political choices were based on the man rather than the platform. Just as he found Jack Kennedy more convivial than Richard Nixon, he may have found Ronald Reagan more convivial than Jimmy Carter. I do think the continuing involvement–he found in it something similar to the adrenalin rush he could get from performing. If you’re Frank Sinatra, you’re a pretty important guy, but you’re not the president.

But Sinatra kept the program until he died, despite how things ended between him and Kennedy. I think he recognized it was a great moment for him and a great friendship. Some friendships don’t last, but the memory does last. The assassination of Kennedy the following year may have contributed to him keeping this. There are other Kennedy items in the sale. I think he regretted that the friendship blew up or ended, but I don’t know that he regretted the friendship.

The condition of Frank Sinatra’s copy is described as “extremities just rubbed, a bit shaken”. Could you elaborate? Any book, if you put it on a shelf, the corners especially tend to get rubbed or worn in something 60 years old. “Just rubbed” means a bit of wear and tear, maybe at the top of the spine where you put a finger to pull it off the shelf. It’s fairly straightforward. “Shaken” is related to the pages, the substance of the book itself, to the binding. It was printed to be a paperback and inserted into the binding to delineate it as a limited edition. The binding is not always the best quality. Literally, if you hold it in your hand and shake it, you’d see the pages were moving. Nothing is sewn into the binding, but nothing is loose.

What does the wear say about Frank Sinatra’s copy of the book, and what does it say about how often Sinatra or his wife might have taken it down from the shelf to look at it or show it to friends? I think it [the wear] is partly that, and partly–I don’t want to be harsh about it–though it was coveted at the time, it was not of the highest quality of manufacture. [The condition reflects] the quality of heavy use and mid-quality manufacture. Let’s put it that way.

The estimate on Sinatra’s deluxe limited edition copy of the 1961 inaugural program is $3,000 to $5,000. That strikes me as a little low. How did you choose that sum? It’s higher than any copy we’re aware of that has sold. Whenever you have a celebrity–and we learned this with the Jackie O estate auction–when there’s special interest with the provenance, it’s best not to build it into the estimate. It’s best to let the marketplace determine where it goes. We say the fact that it was Sinatra’s should increase the value three- or four-fold. In the event of a sale, it may see an increase of more than that.

Are there any notations or inscriptions in Frank Sinatra’s copy the book? There are no notations, but I also think it’s a matter of… during the inauguration, you want to be seen as listening, not taking notes. And it’s pretty chock-a-block. It’s dense. There’s not a lot of space left for notes.

What’s the world auction record for one of these deluxe 1961 inaugural programs? Our estimate is already higher than the highest price. We’re saying that of the copies that have been for sale, this is worth more than any of them. The current record, and this is not quite a one-to-one comparison because it included other material from the 1961 inauguration, such as invitations, it was copy 776, signed by Mr. Foley as chairman of the commission and given to Edward J. Sullivan. It sold at another house for $2,745. Obviously, what we want when people look at the catalog [is to think] “That’s low, I can get it.” We want to pitch the estimate so it’s appealing and will create competition among bidders.

Why will this piece stick in your memory? I’m a huge Sinatra fan. I’ve listened to Sinatra for four decades. And I love association copies–something that underlines a friendship in a tangible way, This is tangible evidence of friendship between two of the greatest figures of 20th century America. It’s really evidence of the culmination of the friendship and probably a highlight for both of them. Kennedy got into the White House, and Sinatra was acknowledged as very important in achieving that goal.

How to bid: Frank Sinatra’s copy of the deluxe limited edition 1961 inaugural program is lot 109 in Lady Blue Eyes: Property of Barbara and Frank Sinatra, a sale that takes place at Sotheby’s New York on December 6, 2018.

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