MS. DIANE REHMThanks for joining us. I'm Diane Rehm. The life of Frank Sinatra was filled with music, women and plenty of Jack Daniels to match. Five years after the biography "Frank: The Voice" became a bestseller, author James Kaplan has come out with his second and final volume on the famous crooner. Kaplan offers a close-up of the man known as Old Blue Eyes, his career highs and lows, his affairs with Hollywood royalty, his exploits with The Rat Pack and his legacy to American culture.

MS. DIANE REHMThe book is titled, "Sinatra: The Chairman." James Kaplan joins me in the studio. I do invite you, as always, to be part of the program. Call us on 800-433-8850. Send your email to drshow@wamu.org. Follow us on Facebook or Twitter. And we will have some favorite Sinatra hits to play for you during this hour. James Kaplan, it's good to see you.

MR. JAMES KAPLANIt's wonderful to be here, Diane.

REHMThank you.

KAPLANThank you.

REHMI must say, this, as I've already said, is your second final volume. In the first, you went through Sinatra's early years. Give us a rough outline of what those early years were like.

KAPLANThe first book is really a story about the rise of a romantic, young troubadour. You know, he's a big band singer until he became so big with Tommy Dorsey that he went out on his own, which no singer had ever done before. And that effectively ended the big band era. The problem was that he made his greatest success early on during World War II with these ballads of longing when all America was thinking about the boys fighting overseas. When the war was over, suddenly, very suddenly, abruptly, American musical tastes changed.

KAPLANSo the first thing that happened, the first bad thing that happened to him after the war was that his records stopped selling. Then, there were about five separate self-inflicted problems that cropped up after that and his career really went down the tubes.

REHMHow long was he married to his first wife, Nancy?

KAPLANThey were married from 1939 until 1950. That was when she changed the locks and called a lawyer because his adulteries had simply become too flagrant, particularly with Ava Gardner.

REHMAnd it was during those years that his fame was escalating or -- I'm just trying to place in my own mind when his misbehavior actually began.

KAPLANRight. Well, there are several chapters of misbehavior, but from 1947 until 1954, he had a terrible -- he called it seven years of Mondays. Terrible career decline. This was not only leaving his wife and young children. This was his records not selling, his record label dropping him, MGM dropped him, his management dropped him. And he married Ava Gardner in 1951. They were a passionate love match, but virtually as soon as they marry, the relationship began to go downhill because her movie career was shooting up, shooting star-wise, and his was shooting down.

KAPLANEverything was going downhill for him and she began to get sick and tired of his moping around. She was very much Frank's equal in a lot of ways and very similar to him, very impatient, very impatient with him. But she did him one enormous favor during those years, during those terrible years. And in answer to your question, the misbehavior really began then. He was very down. He began drinking then. I think that he relied on Jack Daniels for the rest of his life. And whenever he drank, he was a mean drunk.

REHMAnd what was the favor Ava Gardner did for him?

KAPLANWell, contrary to Mario Puzzo's wonderful novel "The Godfather" and the wonderful movie by Francis Ford Coppola, there was no horse's head placed in a movie producer's bed to get the Sinatra-like singer the important movie role in "From Here To Eternity." In fact, Ava Gardner, who had grown sick of Frank's moping around, went to Harry Cohn, the head of Columbia Pictures and told Harry Cohn, who was widely renowned as the biggest lecher in Hollywood, which was saying something in those days, that she would do a movie for him for free is he would give -- if Cohn would give Sinatra a screen test for "From Here To Eternity."

KAPLANCohn looked her up and down and thought, well, what else will Ava Gardner give me for free if she does this movie? So he gave Sinatra the screen test and as it turned out, Eli Wallach, who had done a fantastic screen test, was otherwise engaged doing a play in New York and Sinatra aced the screen test and got the role as Private Maggio and won the Oscar.

REHMIt was an extraordinary portrayal as Private Maggio.

KAPLANIt was. He really identified with that character.

REHMTruly. I must say, there are probably lots of younger people listening and maybe older people as well who are saying, why in the world should we be glorifying Frank Sinatra with either a big second volume biography or an hour on "The Diane Rehm Show." The question becomes, in my mind, for you, how important a figure musically or otherwise Frank Sinatra has been?

KAPLANHe's an enormously important figure. I like to point out that this was a man who, when he was a kid, walked around Hoboken thinking that he heard the music of the spheres. I believe he really did hear the music of the spheres. I believe that this was a man of Mozart-ian level musical abilities, somebody who comes along once every couple of centuries. He was a true musical genius. At the same time, he was a tormented man and as Pete Hamill has so wonderfully said -- Pete Hamill who wrote the wonderful short book "Why Sinatra Matters" and I agree, that Sinatra matters.

KAPLANHis shortcomings were regrettable. His shortcomings were regrettable when he was tormented by many things, when he drank he acted badly. We have many reasons -- I always say that he was a genius in several ways and one of the ways was in making himself dislikable. And so in the ten years I spent writing these books, I very frequently disliked Sinatra, but I was never bored with him for a second.

REHMI understand that very well.

KAPLANAnd I still get goose bumps every time I hear him sing and that is the legacy.

REHMAnd let's do that. Let's hear "I've Got The World On A String" because you say that was one of the songs that really brought him back.

REHMDid he, at this point, have the world on a string?

KAPLANHe did not. He was beginning to have the world on a string, but the way life works, life is always complicated. He had been dropped by Columbia Records and he was signed by Capital Records. A brilliant young Capital executive named Alan Livingston signed Sinatra. When Livingston told his sales force that he had signed Frank Sinatra, they all groaned because Sinatra's career was so down at that point. Livingston teamed up Sinatra with an unknown young arranger whose name you might know, a young man named Nelson Riddle.

KAPLANNelson Riddle arranged this great track. And by the way, this was April of 1953 when Sinatra recorded "I've Got The World On A String." After the final take, after the take was in the can, Sinatra said, I'm back, baby. I'm back.

REHMHe knew it.

KAPLANHe knew it, but he wasn't quite back because at that point, Ava Gardner was in Spain with a bull fighter.

REHMOh, my.

KAPLANAnd he was beginning to make "From Here To Eternity," but it wouldn't be released till August and he had a very rough year ahead of him. It wasn't until the year '53 turned into '54 that the comeback really began. Pantages Theater and the Oscar on that night of March 25.

REHMSo when he found out that Ava Gardner was with a bull fighter, what did he do?

KAPLANIn November of 1953, in the New York apartment of his friend, the songwriter Jimmy Van Heusen, Sinatra slit his left wrist very deeply. He was taken to Mt. Sinai Hospital. The story was put out that he had been hospitalized for exhaustion. It was a very, very difficult time for him. He made -- he came back after a few weeks and was on the "Colgate Comedy Hour," a popular TV show at the time and you could see -- or I can see -- you could see his left cuff, his left of his tuxedo shirt was covering a bandage on his left wrist.

REHMJames Kaplan, his new volume, "Sinatra: The Chairman." Stay with us.

REHMAnd welcome back. What I am so entranced by and have always been is the way that Sinatra could work a phrase, work a note.

KAPLANYes.

REHMMassage each of those.

KAPLANYes, incomparable, and this absolutely, in my mind, unique ability. You hear it a little bit in Billie Holiday, I think a bit in Judy Garland, as well, but there are many great voices out there. Only Sinatra has the ability to make you feel that as he is singing the song, he is feeling these feelings and thinking these thoughts in the moment that he is singing them.

REHMI want, therefore, to go back to his younger days.

KAPLANYes.

REHMTo the days before he began singing professionally. What was he doing that developed this voice? How was his home life?

KAPLANWell, he idolized Bing Crosby as a young guy walking around Hoboken, New Jersey, and he put on airs. I think of -- I think, too, of William Faulkner, who strutted around Oxford, Mississippi. They used to call him Count No Count, another little man who put on airs. Sinatra as a young man in Hoboken felt he was going to be the best singer in the world. Well, what reason did he have for feeling that? He had this incredible ear, an ear that comes along once every couple of hundred years, these Mozart-ian gifts. But nobody knew that until he began to sing.

KAPLANAnd when he first began to sing, the voice wasn't quite there yet. He to develop it. He eventually did take voice lessons, and he studied at the back of the great Tommy Dorsey, studied breath control, he studied phrasing. He also frequented West 52nd Street in New York, which in those days was an entire block of jazz clubs, and heard these great musicians, Lester Young, Teddy Wilson and especially Billie Holiday.

REHMWhat were his parents like?

KAPLANHis parents, his mother was very similar to Frank. Dolly Sinatra was a volcanic presence. She was under five feet tall. She was a Democratic ward healer in Hoboken. She was also a midwife and an abortionist. She was quite a character her whole life. His father was a weak figure in Frank's life. He didn't -- his name was Marty. He was a prizefighter unsuccessful when he was a young man, had tattoos all over his arms. He didn't talk much. He grunted instead of talking. Dolly was the power in the family, and Sinatra loved her, but he was afraid of her.

KAPLANHe said in later years he never knew whether she was going to hug him or hit him, and that was literally the case.

REHMThe artistry of Frank Sinatra's voice is probably as well-demonstrated in this clip as any other.

REHMIt sounds as though he's taking each word and each phrase and putting a velvet layer on it.

KAPLANIt's an amazing album. This is the great Sinatra "Jobim" album he made in January of 1967 with another great musical genius, the Brazilian composer and performer Antonio Carlos Jobim. There's an incredible backstory about this album and about that time in Sinatra's life, but I can say very quickly that this was, despite the gorgeous serenity of this album, this was a time of furies in Sinatra's life, absolute furies.

KAPLANSo many things were going on. He had just married Mia Farrow. Howard Hughes had taken over Las Vegas. Sinatra's credit at the Sands Hotel Casino had been cut off, and in a famous incident the previous September, Sinatra had gotten into a fight with the casino manager of the Sands and had his front teeth knocked out by the casino manager at the Sands. And four months later he's making this sublime album. You just -- there's no accounting for Sinatra.

REHMThere is a question, you bring up Mia Farrow.

KAPLANYes.

REHMAnd the portion of your book regarding his attraction to Mia Farrow, who was how many years younger than he?

KAPLANWhen they married, 30 years younger. She was 19. He was 49.

REHMAnd what he had written was that what he wanted was a young woman who would give up her work and focus solely and completely on him.

KAPLANYes, yes, and that was not Mia Farrow. The initial attraction, of course, was sexual. That was a great deal of it. But also Sinatra was a brilliant man, and Mia Farrow was a brilliant woman, and I think that he was aware of that from the get-go. This was a woman who was deeply sensitive, who was literary, musical and extremely gentle, and I think he really was in love with her for a while. She was also enormously ambitious. She wanted to be a movie star. He did not want her to be a movie star.

REHMAnd he thought that by marrying her, she would agree not to be a movie star?

KAPLANYou know...

REHMI mean really.

KAPLANI mean really, and no, he really didn't see it coming. And I think that -- I think that he felt he was so much in the driver's seat that he could command her to cease working. He told her not to do "Rosemary's Baby," that she would stop doing that movie and come and act with him on this movie called "The Detective." Well, Roman Polanski was shooting very, very slowly. She finished "Rosemary's Baby," and she was served divorce papers on the set of "Rosemary's Baby."

REHMWow. And here is a tweet from Joanne. Does your guest believe that Sinatra was the father of Mia Farrow's son Ronan?

KAPLANI strongly believe, I certainly, I can't prove it. I don't have a test -- I don't have Petri dishes at my disposal. But I can tell you this, a couple of things. Of course many people have made a big fuss about the great resemblance of Ronan Farrow to Frank Sinatra.

REHMExtraordinary resemblance.

KAPLANBut I would direct them immediately to two images. One is a picture of Mia Farrow's late father. He died very young, John Farrow, movie director, who is the spitting image of Ronan Farrow. And I would direct the -- I would direct the listener also to a photograph of Mia Farrow at age 19 on the set of "Peyton Place," where you look at that face, and it is -- she is simply the spitting image of Ronan Farrow.

KAPLANWe all know children who look like one parent or the other. And further, I will just say very quickly that Ronan Farrow was conceived in March of 1987. In December of 1986, Sinatra had had serious intestinal surgery. He had 12 feet of intestine taken out. He was wearing -- there's no other way to say this except clinically he was wearing a colostomy bag. He was -- Frank Sinatra was in Hawaii at that point with his wife Barbara, and he was -- he was more or less incapacitated. He was not the father of Ronan Farrow.

REHMAll right, we've put that one to rest, at least for now.

KAPLANSorry I had to say it, but there's no other way to say it but to say it.

REHMWe'll see what happens. I think that the world really turned against Frank Sinatra when he left his first wife Nancy.

KAPLANYes, yes.

REHMShe seemed...

KAPLANShe's a great woman. She is a great woman.

KAPLANSuch a great woman.

KAPLANShe is a great woman to this day. She is 98 years old. She has her wits about her completely. And she was a kind of heroine of my first book and more in the background in the second book but still a heroine and still a heroine to me, an extraordinary woman, extraordinary woman of great spirituality, of great moral fiber, a wonderful mother to her three children and a woman of enormous patience. I think she never fell out of love with Frank Sinatra despite all his misbehavior.

REHMAnd what did she do after he left her?

KAPLANShe lived her life. She lived her life. She never remarried. She was a mother to her children. People sometimes would ask her why she never remarried, and she would smile and say, after Frank Sinatra, and she meant it. I think they maintained a relationship. Nancy, Big Nancy they call her, Big Nancy and Frank, until the end of his life. And even Frank's daughter Tina asserts that later in Frank Sinatra's life there was still a romantic, occasionally a romantic relationship between his first wife and Sinatra.

REHMLike going home.

KAPLANLike going home, exactly.

REHMAnd he finally died after what?

KAPLANWell, in certain ways it's amazing how long he lived. He died at age 82. His heart gave out on him. He had -- he had cancer, but that's not what killed him. This was a man who, throughout his life, smoked three packs of unfiltered Camels a day and drank probably a fifth of Jack Daniels a day. It's amazing he held out as long as he did. All you can cite is good genetic luck and an enormous life force. But in May of 1988, that heart finally gave out.

KAPLANHis mind had been giving out for a long time. He was on a lot of -- he had self-medicated with Jack Daniels for many years, but then he began, as he lost his faculties, there were a number of medications, and that mixed with the alcohol did not help him.

REHMHow did he live at the end? How was he being cared for?

KAPLANHe was being cared for at home in Beverly Hills. He had to leave his beloved Palm Springs compound, move to Beverly Hills. His wife Barbara saw that he was taken care of. There were in-home helpers. There were nurses. He was seen frequently by doctors, but he became more and more a shut-in, more and more isolated from the world.

KAPLANHe stopped -- his last performance was in February of 1995, and after that there were three years of really just being at home.

REHMJames, we have not talked about the Rat Pack.

KAPLANYes.

REHMTell us about who made that up, how it came together and what was its central focus in addition to liquor and women.

KAPLANWell, I love the way you put it. When you say made it up, that's exactly right. In my mind, the Rat Pack is a grand myth, and it's a myth that's extremely seductive. Even to me, after all I know about it, it's still seductive. It forms really the basis of Sinatra's mystique. It all happened in Las Vegas in early 1960 when several things converged, several factors converged. A movie was being made called "Ocean's Eleven," which of course became the Rat Pack movie, and John Fitzgerald Kennedy was campaigning for president and was stopping in Las Vegas in early 1960.

KAPLANSo you had all these performers, Frank Sinatra, Dean Martin, Sammy Davis Jr., all performed at the Sands, and then the adjuncts, the ancillaries, Peter Lawford and Joey Bishop, and at first it all -- it was all improvised, really. At first all these performers, the three main performers, Frank and Dean and Sammy, were going to, during the weeks of January and February of 1960, were going to perform separately.

KAPLANBut they kind of -- they were making this movie. They were having fun. They began to sort of heckle each other and get up and interrupt each other's acts, and that became the basis of the rat pack. It's -- it all looks and sounds a lot more glamorous than it really was. There an enormous amount of alcohol, enormous amount of misogyny and some very bad racial joking. It doesn't hold up today, about Sammy.

REHMAnd you're listening to the Diane Rehm Show. There was I won't say a moment because it lasted a lot longer than that, when the group, as we shall call them, was apparently, they thought, invited to stay at the home of the U.S. ambassador to London.

KAPLANYes.

REHMJoseph Kennedy.

KAPLANYes, yes.

REHMAnd then what happened?

KAPLANWell, I'm thinking of two different stories, and a similar story I'm thinking of is when President Kennedy in spring of 1962 planned a trip west. I'm not sure if we're talking about the same thing.

REHMI think we're talking about first when they were going to London, and Kennedy had -- the ambassador had purportedly invited them to stay with him.

KAPLANYeah, well, I believe on that stay, on that stay Sammy Davis Jr. might have been disinvited. The ambassador was, how shall I put this, he could be intolerant. But I was also thinking of, if I may, the moment in March of 1962, when President Kennedy was planning to go spend some time having fun and sun at Frank Sinatra's Palm Springs compound.

KAPLANAnd he was abruptly advised strongly by his brother, the attorney general, Robert Kennedy, that he could not, not shouldn't but could not, stay at Frank Sinatra's place. Well, why was this? J. Edgar Hoover had recently notified the attorney general that the girlfriend of the president, a young woman named Judith Campbell, was also having an affair with the head of the Chicago mafia, a man named Sam Giancana. This was a potential powder keg, a scandal of enormous proportions, and Sinatra was the one who had introduced Judith Campbell to the president, and Bobby Kennedy said you can't stay there.

KAPLANThe president stayed instead at Bing Crosby's house in Palm Springs. This was an enormous humiliation to Sinatra, public humiliation. He was furious. He took it all out on Bobby Kennedy and Peter Lawford, who was the bearer of the bad news, and that was the beginning of Sinatra's turn to the right politically.

REHMJames Kaplan, and the second and final volume of his two-volume biography is titled "Sinatra: The Chairman." Short break. We'll be right back.

REHMWelcome back. James Kaplan is with me. His new book, the second and final volume in his biographical account of the life of Frank Sinatra. This volume titled, "Sinatra: The Chairman." And before we go on we should talk about that title, "The Chairman."

KAPLANYes.

REHMWho gave it to him and why?

KAPLANThere was a well-known disc jockey in New York, named William B. Williams on WINS. And he was a huge Sinatra fan. Played Sinatra's records constantly and passionately, sometimes had Frank on the show. And in the late 1950s, William B. Williams, being silver of tongue, simply laid this nickname on Sinatra. It was one of those nicknames like The Boss or The Count or The Duke. The Chairman of the Board, when it -- I was initially going to call this second volume, "Sinatra: The Chairman of the Board," but I felt that it would be more -- it would stronger just to call it "The Chairman" because it really is a book about power.

REHMHere's an interesting email from Susan in Durham, N.C. She says, "Nancy and Frank Sinatra furnished their apartment from my grandfather's store, Zimmerman's Furniture in Jersey City."

KAPLANJersey City.

REHM"And Nancy invited both my grandparents over for coffee. It happened to be the day Frank walked in and told his wife he was leaving her for Ava Gardner. So despite Frank's immense talent, my grandfather always called him that bum."

KAPLANThat bum, sure. Well, he acted like a bum toward Nancy. And, and…

REHMAnd here's an email from Jeff in Cleveland Heights, Ohio. "I've read that Frank Sinatra was extremely difficult to work with when making films in Hollywood."

KAPLANYes.

REHMIn Shelley Winters' book, he refused to do more than one take.

KAPLANYes.

REHMAnd if there were technical problems while filming, too bad.

KAPLANToo bad.

REHMThat shot didn't get filmed. Wonder what your guest has heard of his behavior as an actor."

KAPLANHe hated making movies. He hated it. He was a constitutionally, deeply impatient man. And I don't know if you've ever been on a movie set, but it's like watching paint dry.

REHMYeah.

KAPLANThere's -- the cameras on for 30 seconds, then there's 25 minutes of movie wires and lights around.

REHMRight.

KAPLANSinatra hated that. He knew that his first take was his best take. He felt instinctually that it was his best take. But he became disliked in Hollywood because he didn't play nice. He really only behaved himself for directors who had a strong hand and whom he respected deeply. And ultimately there were three of them. There was Fred Zinnemann, "From Here to Eternity." There was Otto Preminger, "The Man with the Golden Arm." And there was the great John Frankenheimer, "The Manchurian Candidate," Frank's finest movie.

REHMWhat a movie that is.

KAPLANWhat a movie that is. It holds up.

REHMIt certainly does. Let's go to Rick, in Mount Dora, Fla. Hi there. Rick, are you there?

RICKHello. Diane?

REHMYes, go right ahead, sir.

RICKDiane, first of all, it's a distinct pleasure to talk to you.

REHMThank you.

RICKListening forever. And, Mr. Kaplan, I was hoping you could talk a little bit more about Nelson Riddle.

KAPLANYes.

RICKYou mentioned him briefly. You know, for someone to be responsible for that sound that Frank had after he was a troubadour.

KAPLANYes. Yes, he really -- when you're hearing the great albums that Sinatra and Riddle made in the 1950s for Capitol, you are hearing the collaboration. I don't like to throw around the word genius. It's often thrown around. But in this case, in the case of Riddle and Sinatra it is exactly right. This was the collaboration of two musical geniuses.

REHMWhat about "Strangers in the Night?"

KAPLANSinatra hated the song. I'm sorry to say it.

REHMWhy did he hate this song?

KAPLANWhy did he -- he hated the song. This was a period in Sinatra's life when rock and roll had hit the music business like an atom bomb. And Sinatra's old brand of music, which relied so heavily on the great American songbook and standards, was going by the wayside, or so it seemed. Rock and roll was coming in. Sinatra had a new young producer named Jimmy Bowen.

KAPLANJimmy Bowen heard this melody in a spy movie of all things, James Garner's spy movie. The melody was composed by a German named Bert Kaempfert. And Jimmy Bowen, the producer, said if you can get me a lyric to that song I can make it a hit. And he got a lyric and he brought it to Sinatra and they made it a hit. But Sinatra hated the song. He hated it with a passion. He would announce in concert, I hate this song.

REHMReally?

KAPLANHe would sing it anyway 'cause people loved it.

REHMAll right. Let's go to Bob, in Hershey, Pa. You're on the air.

BOBHi, Diane. Thank you.

REHMSure.

BOBI was wondering -- I had heard this and wondering if Mr. Kaplan can comment on -- all those years working with Tommy Dorsey, is it true that Frank Sinatra kind of developed the phrasing of the notes the way he sang, kind of to be similar to the way a trombone plays, kind of extending them out, bringing it back? And I had another question. I've never heard anybody talk about it. I'm wondering role, if any, you know, did Frank have any religious beliefs and were they expressed in any particular way?

KAPLANWell, to answer the first, Frank was not particularly religious. He would go to church every once in a great while. But perhaps he felt that even confession could not absolve him of all his manifold sins. Not very religious. And what you say about Tommy Dorsey is exactly right. Tommy -- Sinatra sang with Dorsey's band from 1939 until late 1942.

KAPLANDorsey was a brilliant trombone player with incredible breath control, incredible phrasing. And Sinatra picked up a great deal from Dorsey, including a trick of holding his breath for what seems, when you listen to him, an incalculably long time.

REHMHe did a lot of swimming…

KAPLANYes.

REHM…in order to do that.

KAPLANSwam laps underwater to build up his lung power. And when he made an album he would go into training and he would cut down on his smoking, believe it or not. Cut down from maybe three packs a day to one pack a day. But he was -- Sinatra, he was very impatient on a movie set, but when it came to recording, that's where it all was for him. And he would do as many takes as it took.

REHMSomebody once said they stood behind him trying to watch how his back might move…

KAPLANYes, yes.

REHM…so that they could understand his breath control. And then someone spoke about a hole in his mouth.

KAPLANYes. Well, Tommy Dorsey had a trick, since he was a trombone player, of taking a sneak breath. He would widen his mouth and at each side of the mouthpiece -- you couldn't quite see it because the mouthpiece obscured most of his mouth. He would widen his mouth and form tiny openings on each side of the mouthpiece and take in a breath

KAPLANIf you watch Sinatra on YouTube, watch him on any video where he is singing, you occasionally see him do something that looks almost like a smile. He widens his mouth. It's exactly the same thing that Dorsey did. And he takes a breath from the corners of his mouth, in the same way.

REHMInteresting.

KAPLANYeah.

REHMI want to ask you about two other women in Frank Sinatra's life. Lauren Bacall.

KAPLANYes.

REHMAnd Marilyn Monroe.

KAPLANYes. Well, Lauren Bacall was an almost. There were rumors that Frank Sinatra and Lauren Bacall were having an affair, even while Bacall's husband, Humphrey Bogart was sick and then lay dying. They're very unpleasant rumors to hear, but I think they might have been true. After Bogart died in early 1957, they dated heavily, Sinatra and Bacall. And Sinatra, indeed, proposed to Bacall.

KAPLANBut a very unfortunate thing happened. A friend of theirs, a literary agent named Swifty Lazar was present when Frank popped the question. Lazar leaked the news to the gossip columns. And the news got out and Frank flew into a fury that this news had been leaked. He wanted it kept private. He wanted it kept just between him and Bacall.

REHMBut why would he do it when Swifty Lazar was present if he wanted it kept quiet?

KAPLANTina Sinatra said, "My father -" his third child. "My father was a deeply feeling man who was unable to attain an intimate relationship." That was the pattern for Sinatra's life. And so here you have a man who asked a woman to marry him with another person present. Sinatra lived in the public. He often -- he most often hated it. But he lived in the public. He couldn't stand to be alone. At the same time he couldn't form an intimate relationship.

KAPLANAnd when it came to Marilyn Monroe, the same held true. Marilyn Monroe was a deeply needy woman. She was a train wreck. And worst of all for Sinatra was the fact that her personal hygiene was not the best. She was a mess. Every place she lived was a rat's nest, with books and bottles and God knows what lying all over the floor. She was frequently disheveled, not always washed. Sinatra was obsessively clean. He took three or four showers a day.

KAPLANHis fingernails were exquisitely manicured. So despite the fact that he felt deeply for her -- he called her Norma Jean, which was her real name -- felt deeply for her and I think loved her in his way -- and of course there was a sexual attraction -- it was never a relationship that was going to stay for that reason.

REHMWas it he who introduced Marilyn Monroe to President Kennedy?

KAPLANIt was. And it was a relationship that Marilyn Monroe became obsessive about. And President Kennedy, in his extremely pragmatic way, was fascinated and titillated and then when time came to move on, as he always did, he moved on.

REHMBut his brother?

KAPLANHis brother, Robert Kennedy, I think had a kind of a big crush on Marilyn Monroe. And Marilyn Monroe, with her fascination with the president, formed a kind of fascination by proxy with Robert Kennedy. But it wasn't -- there wasn't the same animal magnetism there.

REHMAnd you're listening to "The Diane Rehm Show." I think one song that sort of epitomizes Frank Sinatra and his manner of living life in his own way is this one.

REHMTell me about this song, James.

KAPLANFrank didn't like the song. It was written by Paul Anka and Sinatra felt that the lyrics -- he was -- Sinatra was always exquisitely attuned to lyrics and lyricists. He felt that the lyrics of the song were too on the money, too direct. And at the end, that they were too boastful. And he was a swaggering man, a man of enormous presence and ego, but he was not a braggart.

KAPLANHe was not a braggart. He felt the song was braggartly and he would announce to audiences he didn't like the song. But audiences demanded it. And so much of what makes a superstar is what we feel about that star. We want "My Way" to reflect Sinatra's soul. It feels like it should reflect Sinatra's soul. He was more complicated than that, but that's hard to tell audiences.

REHMAnd it's so interesting, as you mentioned, that he made a right turn…

KAPLANYes.

REHM…politically.

KAPLANYes, he did.

REHMWhich is also somehow epitomized by this song, "My Way."

KAPLANYes, he did. He began campaigning for Ronald Reagan for governor in 1970. And his many Democratic friends -- Frank had been a dyed-in-the-wool FDR Democrat -- were horrified. And Sinatra said -- Sinatra told them I am going to do what I please and he did.

REHMJames Kaplan, what a pleasure to talk with you.

KAPLANAbsolute pleasure to talk with you, Diane.

REHMThank you. The book is titled, "Sinatra: The Chairman." Thanks for listening all. I'm Diane Rehm.