Sinatra and the Jack Pack: The Extraordinary Friendship between Frank Sinatra and John F. Kennedy?Why They Bonded and What Went Wrong

Sinatra and the Jack Pack: The Extraordinary Friendship between Frank Sinatra and John F. Kennedy?Why They Bonded and What Went Wrong

by Michael Sheridan, David Harvey

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A New York Times Bestseller

Frank Sinatra desperately wanted to be part of John F. Kennedy, Jr.’s gang. He had his own famed “Rat Pack,” made up of hard drinking, womanizing individuals like himself—guys like Dean Martin, Sammy Davis, Jr., and Peter Lawford—but the guy “Ol’ Blue Eyes” really wanted to hang with was Lawford’s brother-in-law, the real chairman of the board, John F. Kennedy.

In Sinatra and the Jack Pack, Michael Sheridan delves deep into the acclaimed singer’s relationship with the former president. He shares how Sinatra emerged from a working class Italian family and carved out a unique place for himself in American culture, and how Kennedy, also of immigrant stock, came from a privileged background of which the young Frank could only have dreamed.

By the time the men met in the 1950s, both were thriving—and both liked the good life. They bonded over their mutual ability to attract beautiful women, male admirers, and adoring acolytes. They also shared a scandalous secret: each had dubious relationships with the mafia. It had promoted Frank’s career and helped Kennedy buy votes. FBI Director J. Edgar Hoover had, over two decades, compiled detailed and damning dossiers on their activities.

From all accounts the friendship thrived. Then, suddenly, in March 1962, Frank was abruptly ejected from JFK’s gang. This unique volume tells why. It will release shortly after a television documentary inspired by the book airs, is filled with a beloved cast of characters, and is the compelling, untold story of a tumultuous relationship between two American icons.

Skyhorse Publishing, as well as our Arcade imprint, are proud to publish a broad range of books for readers interested in history--books about World War II, the Third Reich, Hitler and his henchmen, the JFK assassination, conspiracies, the American Civil War, the American Revolution, gladiators, Vikings, ancient Rome, medieval times, the old West, and much more. While not every title we publish becomes a New York Times bestseller or a national bestseller, we are committed to books on subjects that are sometimes overlooked and to authors whose work might not otherwise find a home.

Product Details

ISBN-13: 9781510703711
Publisher: Skyhorse
Publication date: 04/19/2016
Format: NOOK Book
Pages: 276
Sales rank: 189,441
File size: 4 MB

About the Author

Michael Sheridan is one of Ireland’s most successful authors. He has been published in thirty countries, has a number of bestsellers under his belt, and has combined sales of more than 650,000 books. He was the also the main screenwriter and coproducer of the feature film When the Sky Falls. It was financed by Sky Films and distributed by 20th Century Fox. Sheridan lives in Ireland.

Read an Excerpt

Sinatra and the Jack Pack

The Extraordinary Friendship Between Frank Sinatra and John F. Kennedy â" Why They Bounded and What Went Wrong

By Michael Sheridan, David Harvey

Skyhorse Publishing

Copyright © 2016 TwoDeeTV
All rights reserved.
ISBN: 978-1-5107-0371-1


The Beginnings

415 MONROE STREET was an unremarkable building on an unremarkable street in the unremarkable town that is Hoboken, New Jersey. A four-story tenement surrounded by many of similar size and some much smaller, one and two story, the sort of buildings that defined the immigrant communities that grew up on both sides of New York's Hudson River in the late nineteenth and early twentieth centuries. From the top of the building, located just twelve blocks from the shoreline, you could see the three churches of St. Ann, St. Francis, and Our Lady of Grace and St. Joseph, established in the area to cater to the optimistic Catholic emigrants who had streamed into the town hoping for a new life in America. Beyond these places of worship was the growing skyline of Manhattan, where some of the neighborhood's residents traveled daily to try to make a living.

For many people, the American dream had come to a crashing halt in Hoboken, just five miles from where they had entered the United States at Ellis Island, the nation's busiest immigration inspection station from around the turn of the nineteenth century. For Italian peasants from as far apart as the picturesque shores of Lake Como in northern Lombardy to the arid and tiny towns of Ragusa in southern Sicily, the hope of wealth and prosperity had given way to the harsh reality of life at the bottom of the immigrant ladder in the New World. At the time, German merchant classes occupied the top rung, a trend that would decline rapidly as a result of anti-German sentiment at the outbreak of World War I. Their dominance was followed by the Irish, who controlled the police and fire services, leaving the scraps for the Italians, many of whom arrived in the country without papers, prompting the denigrating nickname "WOP."

Saverio Antonino Martino Sinatra was just twelve when he passed through the Ellis Island inspection in 1904 with his mother, Rosa, and his sisters, Angela and Dorotea. Francesco, his father, had traveled ahead and was already working in a pencil factory when his family arrived. Rosa appears not to have considered education essential to her son's advancement, and Saverio, who had adopted the more Americanized moniker of "Marty," remained illiterate. First apprenticed as a shoemaker, he turned in his late teens to prizefighting, adopting the pseudonym "Marty O'Brien," possibly to ingratiate himself with the Irish locals but more likely because Italians were not allowed in the fight game. Marty had tattoos drawn all over his arms, but with a slight build and an asthmatic condition, he did not come across as fearsome or threatening, neither to his opponents nor to the local street gangs. He was also too laid back in personality to make any impact either in, or outside, the ring.

He had, however, made an impact on Natalie "Dolly" Garavente, another Italian immigrant who lived nearby. Dolly had left the town of Rossi in Liguria, northern Italy in the late 1800s and had settled with her family in Hoboken. Dolly and Marty had been seeing each other since late 1910, when she had just turned fifteen and he was eighteen, and Dolly would dress up in her brothers clothes, hair bunched up under his cap, to go to Marty's bouts in a time when women were not allowed at boxing matches. Dolly's brother, Dominick, was also a disguised Italian fighter and regular opponent of Marty's.

The Ligurian Garaventes had little time for the Sicilian Sinatras and regarded the illiterate Marty as highly unsuitable for the daughter of a family keen on bettering itself. As a result, Dolly's parents refused to countenance the relationship. When the Garaventes refused point blank to host a wedding, Dolly and Marty eloped. The most romantic destination within their means was Jersey City, four miles down the road, and it was there, in the city hall, on Valentine's Day 1914, that they were married. The bridegroom's occupation was registered as athlete, and the couple's friends Anna Caruso and Harry Marrotta witnessed the ceremony. It was a tribute to Dolly's courage to go down this path without her parents' blessing and against the background of the importance of the act of marriage in the staunchly Catholic ethos of Italian culture, and all the more so among the immigrant community. It was also a vote of confidence in Marty who, although kind and decent in every respect, did not engender much confidence as a potential breadwinner. The couple would not starve though, because of the money Dolly's mother made at her grocery store. But they had two great assets, the bond that had kept them together and Dolly's ambition and maturity beyond her tender years.

When the dust from the secret wedding eventually settled, Dolly's parents grudgingly accepted the union and the couple settled on Monroe Street. It was in a small, dark room of the tenement house, on December 12 of the following year, that the most life-changing event of the young couple's lives was to occur. Dolly had become pregnant in the late spring, and as she began her labor the local midwife attended her, as was the custom in the community. Professional medical care was beyond the means of most, and with her sister and mother by her side, Dolly knew she would be delivering her baby with the most experience and attention at hand that she could hope for. After hours of labor, things seemed to stop abruptly, and Dolly was suddenly in great distress. This was most likely because at less than five feet in height, she had a small pelvic area, and the baby was so large that she couldn't push any longer because of exhaustion. At once, everyone in the room became increasingly worried by the progress of the birth. Sensing danger and realizing that the solution was beyond her skills, the midwife called the local doctor. Ten minutes later he arrived, quickly recognized that this had to be a forceps procedure, and literally ripped the baby from the exhausted mother's womb. The action, however crude, had been a matter of life and death. The doctor had not had time for niceties, knowing full well the potential consequence of two deaths as opposed to one. Safely delivering the child while making sure the mother survived was his priority in a time when infant mortality was extremely high.

A baby boy, weighing an enormous thirteen and a half pounds, was delivered with wounds to the left side of the head, including a scarred ear and a perforated eardrum. These would have a lifelong consequence for the baby, and the awful difficulty of the birth and its conclusion would ensure that Dolly would never give birth again. But nobody was inclined to blame the doctor, who after the delivery turned his medical attention to the mother and, in effect, played the role of lifesaver. The baby's grandmother, concerned that the baby appeared lifeless, put him under a cold tap until he started to cry. In a time when most, if not all, births in deprived areas were at home and the chances of survival up to a year were less than fifty-fifty, the event was unremarkable for the denizens of this Italian ghetto, who were preparing to gather whatever meager means they could for Christmas. Generations later there would be more reason to remember it as the day that Francis Albert Sinatra entered this world.

From the start of their tenancy of the Monroe Street address, Dolly had cast her eyes on a better life, and the birth of Francis Albert provided a fresh impetus to her aspiration to leave the stench of poverty behind. As far as she was concerned, their tenancy of number 415 was to be as brief as possible, and no source of retrospective pride. She had her sights firmly set on the better side of the city, and that meant that she was not going to subscribe to the traditional role of stay-at-home mother. The money had to come in, and whatever that took she was prepared to do. This meant that for the foreseeable future her beloved son would be minded and brought up by the extended family. If the possible consequences of this for little Francis ever crossed Dolly's mind, she stuck it in some mental drawer and threw away the key.

Hoboken was not the worst place to be if you lived on the right side or you took, or were given, decent opportunities, although being Italian was a definite minus in that regard. The Hoboken community had been formed as a township in 1849, and after a referendum six years later attained the status of a city. By the late part of the century, shipping lines were using it as a terminal port, and a railroad terminal was established on the waterfront. It was a bustling area with the busy Hudson River as its commercial focus. Hoboken was the major destination of the Hamburg line, the main carrier of immigrants from Germany to the United States, hence the large German population in the city and its environs. Shipbuilding and dry-dock activity had also become a major source of employment, as had some rapidly growing manufacturing enterprises and big companies such as Maxwell House and Lipton's Tea. There was always work if you knew the right people, and Dolly set about acquiring some skills and cultivating connections, which, somewhat unusually for an Italian, were based among the Irish community.

Her first move in that direction came while she was recovering from the birth and planning little Frank's baptism, which she would not attend. She bucked the long-established Italian tradition of choosing godparents from within the close family circle by asking Frank Garrick, an Irish friend of Marty's, to be godfather. Garrick's father, Thomas, happened to be a local police captain, and Dolly felt he could potentially do much more for her Frank than any Italian relative or friend. The godmother, Anna Gatto, was Italian though, and the ceremony took place in St. Francis Church on April 2, 1916, when Frank was four months old.

Dolly had been planning her next move. She knew how valued midwives were in the community, and how they always retained a strong residual loyalty from those whose babies they had brought into the world. So as soon as she was fit and able, Dolly elected to become one. Her informal training consisted of accompanying doctors who were called to home births until such time that she was able to do it on her own. A doctor was not within the budget of most of the Little Italy occupiers and other immigrant groupings all over the greater New York area, so the midwife became the principal assistance at birth. In time, Dolly would be seen running around the neighborhood carrying a little black bag and looking like a medical professional. The best of midwives were very good but, as Dolly's personal experience had illustrated, often not good enough when complications arose in the process of giving birth.

If her newfound role was in some way inspired by the horror she endured when bringing her son into the world, her later "diversification" of her services would confirm Dolly's ruthless drive to acquire the means to improve the family's social status. That drive would not be interrupted by any moral considerations or religious constraints. Within a couple of years she had amended her midwife role, one which was charged with assisting the safe passage of the unborn, to assisting the very opposite. Dolly Sinatra became a backstreet abortionist and did so because destroying the unborn was more lucrative than saving it. The instruments of the abortionist were simple and crude; the modus operandi was to break the amniotic sac inside the womb with a sharp instrument. For Dolly, it was a long hatpin regarded as a fashion item of the time, giving her the nickname "Hatpin Dolly."

For over half a century there had been a somewhat ambivalent attitude toward abortion. The church and most doctors opposed it and the press vilified it, but the law in general accommodated it, probably because rich and powerful society figures availed of the service to avoid shame or diminution of reputation. The most famous American abortionist was Mrs. Ann Lohman, aka Madame Restell, or Madame Killer, as she was better known. She operated a high-class abortion clinic in Manhattan but franchised her services to others including a woman in Hoboken by the name of Frederika Loss. This female abortionist and tavern owner who had a farm in the Hoboken and Weekhaven area had become a major player in one of the most famous and sensational unsolved murder cases in American criminal history. The case involved a beautiful young woman by the name of Mary Rogers, who worked in a famous Manhattan cigar shop owned by John Anderson. In July 1841 she sought, in some sense of desperation, a loan for an "emergency," and her employer duly obliged without explanation of the nature of the emergency. On the weekend of July 25 she told her widowed mother, who ran a boarding house, and her fiancé, a boarder, that she was going to visit an aunt and other family. Three days later her battered body, with severe blunt trauma to the face, was fished from the Hudson River in Hoboken. The coroner found strange wounds in the area of the vagina. The beauty of the victim and the strange circumstances of the case created a media frenzy, and all sorts of theories arose to explain the case, not helped by a totally incompetent police investigation.

In November 1842, Frederika Loss came forward and gave a sworn statement that the death was a result of a failed abortion attempt, but she was ignored by the police despite the fact that items of the victim's clothing had been found on the farm and that it was well known that the tavern served as an abortion location for Madame Restell's operations. The crime remained unsolved, but the Police Gazette of February 21, 1846 produced an unequivocal attack on Madame Killer:

It is well known that females die in ordinary childbirth. How many then who enter her halls of death may be supposed to expire under her execrable butchery? An obscure hole in the earth; a consignment to the savage skill of the dissecting knife or a splash in the cold wave, with the scream of the night blast, for a requiem, is the only death service bestowed upon her victims. Witness this ye shores of Hudson. Witness this Hoboken beach!

Three decades later, there was still demand for abortion, and Hatpin Dolly was carrying on the long-established tradition in Hoboken. Despite the threat of prosecution if caught, she would have been very aware that her clients would, almost always, keep their silence and thereby make any legal action almost certain to fail. Dolly had by this time become something of a politician. She had a great ear for language and dialect and would get involved as a translator for her fellow Italian immigrants when they appeared before the courts. She also hooked up with the Democratic machine of New Jersey's Hudson Company and acted as a conduit between Italians and city hall. Helping to deliver votes, and ensuring that favors were organized and returned, put her in an increasingly strong position in both the Italian and Irish communities, and her tenacious, organized approach to political clientelism ensured that she was very quickly becoming someone to be respected. She was rewarded for her unstinting work when she was appointed leader of the third ward in the ninth district, a position never before held by a woman. This was by no means a sinecure, as it was not a paid job, but Dolly knew full well that when the time came she would be able to reap whatever reward she might seek.

As Dolly expanded her business and developed her local connections, there was an unexpected boost for her fortunes when in April 1917 the United States entered the First World War. The first local consequence was the taking over of the Hamburg American line piers and the establishment of federal control over the port. The German domination of the commerce of Hoboken came to an abrupt end with martial law imposed on the area. Many of the local German families were summarily removed to Ellis Island while others simply left the city. The Irish now firmly occupied the top rung of the local immigrant ladder, and Dolly, with her connections, was poised to profit from her work on behalf of her political masters. The exit of her family to a better side of the city was moving closer to reality.

* * *

On October 7, 1914, the same year that Marty and Dolly had married, another couple had tied the knot two hundred miles away and in very different circumstances. Their antecedents, however, were not so far removed from the origins of the Sinatras. Another aspect that provided an echo to their situation was the resistance of the parents of the bride to the bridegroom. In terms of wealth and influence the marriage of Joseph P. Kennedy and Rose Fitzgerald united two of the most powerful Irish families in the Boston area. But their origins, in particular on the Kennedy side, could have been easily forgotten by the passage of time, as often happens when money and position conspire to obliterate the facts of the past. The history of all Irish immigrant families, at the time, was grounded in extreme poverty.


Excerpted from Sinatra and the Jack Pack by Michael Sheridan, David Harvey. Copyright © 2016 TwoDeeTV. Excerpted by permission of Skyhorse Publishing.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Table of Contents


Chapter 1: The Beginnings,
Chapter 2: The Matriarch,
Chapter 3: The Patriarch,
Chapter 4: Shadow of a Gunman,
Chapter 5: An American Dream,
Chapter 6: Frankie Goes to Havana,
Chapter 7: Kennedy's Irish Mafia,
Chapter 8: Sinatra in the Garden of Ava,
Chapter 9: Kennedy Steals the Show,
Chapter 10: The Jack Pack,
Chapter 11: The Road to Glory,
Chapter 12: The Golden Dawn of Camelot,
Chapter 13: Hoover Turns the Screw,
Chapter 14: The Trip,
Chapter 15: Assassination,
Chapter 16: The Wilderness Years,
Chapter 17: The Final Curtain,
Photo Insert,

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Sinatra and the Jack Pack: The Extraordinary Friendship between Frank Sinatra and John F. Kennedy--Why They Bonded and What Went Wrong 3.6 out of 5 based on 0 ratings. 5 reviews.
Anonymous More than 1 year ago
Good show!
Anonymous More than 1 year ago
More about Kennedy than Sinatra.
Mahuenga More than 1 year ago
I never thought I’d read a biography that was a page-turner. Wrong. The title alone suggests a modern mash-up, and it does not disappoint. This creative writer lays out two intertwining stories, well-woven. Clever use of modern cultural terms and concepts made the work fresh and accessible, without overshadowing the nostalgia of the time periods he writes about. There were parts of the historical narrative that I’d never read before. Although Sheridan’s opinion(s) on the men were evident, I felt that he presented the subject matter fairly, even debunking an oft-repeated myth about the Kennedy family.
Anonymous More than 1 year ago
Interesting. Fame and fortune equals politics. Disturbing.
Anonymous More than 1 year ago