Wiseguys and the White House: Gangsters, Presidents, and the Deals They Made – An Authoritative Exposé of the Mob's Secret Influence on American Political Power

by Eric Dezenhall

A “connected” account of how the Mob has worked with America’s Commander in Chiefs and have influenced the presidency for nearly a century.

Gangsters and presidents have long captured the American imagination, but how much does the underworld actually affect presidential power? How deep are their “connections”? As Eric Dezenhall reveals in this eye-opening history, in some instances, one couldn’t have functioned without the other. From Franklin Delano Roosevelt to Richard Nixon to Joseph R. Biden, the mob has done presidential dirty work, including attempts to assassinate foreign leaders, harass America’s enemies, and put our chief executives in office.

Wiseguys and the White House documents when mobsters and presidents have traded favors—and double-crossed each other, including:

• The deal cut with Lucky Luciano to protect the waterfront during World War II.
How the Chicago Outfit (and Frank Sinatra) got one Kennedy elected, only to be pursued by another.
• How LBJ and the FBI used a mob hitman to hunt down the killers of Civil Rights activists in Mississippi
• Reagan’s association with Lew Wasserman, the powerful and influential Hollywood mogul
• Trump's blatant ties to construction and gambling cartels
Biden’s early links to “the Irishman” Frank Sheeran, the labor union official and enforcer for Jimmy Hoffa and Russell Bufalino.
• And more

Combining exhaustive research, including newly released government records and the private recollections of leading gangsters, Wiseguys and the White House offers insight into the myths about the power in America and the drive for recognition and respectability that unites consiglieri and commanders-in-chief alike.

Genres: History, Nonfiction, True Crime, Politics, Crime, American History, American

368 pages, Hardcover

First published January 14, 2025

About the author

Eric Dezenhall is a journalist and author of twelve books, including three non-fiction texts on crisis communications. Other areas of expertise include organized crime and the intelligence community. He is the Chairman and co-founder of Dezenhall Resources, One of the country's first crisis communications firms. He lectures in academic and business circles and appears in international media including NPR, CNN, FOX, CNBC, MSNBC and the History Channel. He has written for the New York Times, Wall Street Journal, Los Angeles Times, and USA Today.

Eric’s work is widely cited in business, media, and academic circles. His book, Best of Enemies with Gus Russo, is being made into a feature film. He is also the author of seven novels, including The Devil Himself, based on the true story of the U.S. Navy’s collaboration with organized crime in WWII. His latest non-fiction book, Wiseguys and the White House, documents when mobsters and presidents traded favors -- and double crossed each other. Eric graduated from Dartmouth College and lives near Washington, D.C., with his family.

Reviews

[Erin · Rating 4 out of 5]

"I've got to be the cleanest, I think I'm the most honest human being, perhaps that God has ever created"

-Donald Trump

When I told my dad and sister I was reading this book I asked them both who they thought was the most mobbed up?

They both gave the same 2 names: John Kennedy & Donald Trump.

While both of those presidents are included in this book, they are not the correct answer. The correct answer would be at least to me a very surprising name....Harry Truman. Truman never has a political career let alone does he become president without the mafia....and he repaid them handsomely for their hard work.

"When I sell liquor, it's called bootlegging; when my patrons serve it on Lake Shore Drive it's called hospitality "
- Al Capone

I've read enough books about JFK to know his family's mob ties are vastly overblown. Same can be said about Trump, he loves to brag about mob ties but there is little evidence that he had any more connections than any other person doing high level business in New York City.

I won't tell you who else in this books mob ties surprised me ( including the president with ties to someone in the Scorsese film The Irishman)because I want you guys to read it and be shocked as well.

I highly recommend this book, to my political junkies who also enjoy crime.

[Sydney Darwin · Rating 4 out of 5]

As someone who has always been super interested in government and politics this was a wonderful read. Detailing mob involvement all the way back to FDR through the current administration. I found the LBJ section to be particularly interesting.

All in all— if you are someone who enjoys non-fiction I think this is a super cool read. Learned lots of things about former presidents and the mob that I could not have even fathomed before picking this one up!

[Marcy · Rating 5 out of 5]

“The most important is the sheer frequency and presence of the mob in the American power structure”. This is the bottom line in this well written, extensively researched, compulsively readable, fascinating and eye opening book. The author’s notes a must. 5+

[Thomas George Phillips · Rating 1 out of 5]

A purely, partisan, so called expose, on certain presidents; none of which were Bill Clinton or Barrack Obama. And both men had Chicago connections to the Mob.

[Eric Keisling · Rating 5 out of 5]

Wiseguys and the White House by Eric Dezenhall is an upcoming book about the relationships between Presidents and organized crime from FDR to Biden. Thanks to Harper for the ARC! The book explores FDR, Truman, Kennedy, Johnson, Nixon, Reagan, Trump, and Biden and the degree to which each President was influenced by the mafia and other rackets. Much of our understanding of the way President have interacted with the mob is urban legend or hearsay, but the degree to which some presidents have either benefitted from the Mafia or otherwise employed them while in office is at times staggering. The story of the Johnson administration sending a hitman to solve the mystery of missing civil rights workers is particularly shocking. Also, the strength of connection between Truman and Pendergast was pretty jarring. While most presidents tried to hide their mob connections, only President-elect Trump has bragged about his mob connections on TV and has done little to hide his previous work with the mob particularly in NYC and Atlantic City.

I found this book both incredibly informative and very entertaining. There’s something about the mafia and the presidency that has endless intrigue and Dezenhall does a great job of telling the stories. If you’re a history fan or someone who enjoys reading about the presidency, this one is a must read when it comes out in January.

[DeWayne Neel · Rating 3 out of 5]

All elected officials have the opportunity to be influenced by some special influence, and the mod took advantage of the opportunity. The actual positive or negative impact that this influence had on future policy is not fully known, but it makes for good TV and news conspiracies. This book looks at the mod and the known contacts from the criminal world and examines possible wrong doing. Everyone wants to be friends with the "popular," and even being pictured in the background could give a person or even the mob a key to open the door to possible influence over someone. It seems in our USA history we have had some "pretty criminals," when we observe the movies and TV specials, that make those connections look good. So they were friends, but did that social environment impact policy? I think not in most cases. Are our political leaders perfect? By no means, but one must look beyond the media moment to locate the real influence on public policy. Now, love life stories, have a long traffic life for even presidents, but we have a way of forgiving those discrepancies.

[Chester Bishop · Rating 4 out of 5]

Hot take…… they’re all crooks. There’s something to be said for the ones that admit it. This book will tell you just that. Believe what you want. Cheer for your team. Hate the other side. Doesn’t matter what side you’re on they have figured that making you scared is the way to control you. Blue, red, la familia, la cosa nostra….. all there to scare you into doing what they want. It’s happened since the history of ruling and being ruled.
All in all, it was very interesting. A lot of information to process. I feel better about the “Presidents” category for Monday night trivia.

4-5-3

4 for the story and the content. Right up my alley.
5 for Joey “socks” Lanza who was known to sock someone in the face with a fish when needed.
3 for my conspiracist rant.

Honorable mention 5 for mentioning Taylor Swift in the book for no reason except maybe it’ll get other people to read it. Bravo.

[Matt- History on the Hudson · Rating 4 out of 5]

Wise Guys and the White House by Eric Dezenhall offers a fascinating dive into the intricate connections between the Underworld and the most powerful office in the world. Dezenhall provides a compelling perspective, shedding light on various presidents and their intriguing ties to organized crime. These captivating stories are brought to life with Dezenhall’s exceptional attention to detail, unraveling the complex circumstances that drove some of our nation's leaders to rely on the shadowy realm of the underworld. This unique history is a great blend for the both the political crowd and the mafia enthusiast.

[Nancy Rowley · Rating 5 out of 5]

Very interesting book based upon facts! There have been rumors/stories about the involvement of the mob and the known characters! However, the author focused on the mob involvement in Presidential politics! Some surprising, some not! It was interesting to see how in some cases—the Kennedy’s, Biden and Trump, the connection began with their fathers! Worth the read!

[Julie · Rating 4 out of 5]

Interesting book about the gangsters who want their help with the Presidents and what they wanted to achieve with their help. He writes about FDR, Richard Nixon, LBJ, Ronald Reagen, John Kennedy, Joe Biden and Donald Trump. Non-Fiction

[Momof4 · Rating 1 out of 5]

This should have been a book more about organized crime than about organized crime and the White House. I found the connections between the two anecdotal at best and inferential at worst. Dezenhall’s “wise guy” writing style bogged down the pace of the book to the point that the subject matter became lost.

Cannot recommend.

[Aaron · Rating 3 out of 5]

In D&D and one too many RPG games, certain character types are known to have certain default traits: wizards with intellect boosts, warriors with advanced strength. Can we make the jump to fantasy to reality and see something similar play out in actual societies? I think so. It’s a weird thing with us Americans: we may naturally carry a preset interest in both presidential politics and organized crime. Thus, a book like Wiseguys and the Whitehouse: Gangsters, Presidents, and the Deals They Made even for those not normally into non-fiction, books on political history, and even written deep dives about the mob may in fact find something that makes them want to check out something they normally may glaze over.

This is a good book, but don’t go in thinking it’s going to be Sopranos in text form; for the most part, it’s pretty dry (but not too dry!) history looking at how past presidents may have got where they where because of mob connections. Some are surprising (see below), some are obvious, and a handful of presidents are skipped over presumably because there just isn’t enough credible evidence out there.

Truman was especially interesting. In Freedom From Fear, a book I coincidentally read only about a month ago, he was painted as clean as a whistle to an almost boring degree (at least compared to your average political figure of the era). Here, in Wiseguys and the Whitehouse, while he still may be seen that way, it’s not as clear-cut due to his alleged connections to Tom Pendergast and the organized outfit in Kansas City. It seems that when you get to positions of power of such high prestige, it may be entirely impossible not to get a little dirty—either directly or at the very least by association. This is something we should keep in mind when judging those who have spent time behind the Resolute Desk in 1600 Pennsylvania Avenue.

One of the more surprising takeways only comes into play near the end: could organized crime in USA only have grown so popular if it wasn’t for the threat of communism along with the almost five decades Hoover remained in charge of the FBI? There may be a connection to be found and while the focus here was on presidents and the mob, one that detaches from the multiple administrations of the twentieth century and zeroes in on just one in another borough may make for even more enlightening reading on the real reasons for the rise and fall of LCN.

[Richard West · Rating 5 out of 5]

If you want to insult a criminal, the worst thing you can call them is a politician. Yet throughout our history, politicians and criminals have made strange bedfellows, often working together. Don't believe it? Read this book and you'll change your mind.

Starting with Franklin Roosevelt, and working up through the administrations of Truman, Kennedy, Johnson, Nixon, Reagan, Trump and Biden, we get an insightful look at how the Mob has influenced much of what happened during some of those administrations. Eisenhower, Ford, Carter, Clinton, both Bushes and Obama were left out of the mix, presumably because they didn't enjoy the relations with the Mob that the others did.

We get the inside story - some of which, like JFK - is more than just a little familiar. Others, not so much. And what we wind up with is an insightful, well-researched look at how some of what have been called "our finest men" were influenced by the Mob, how the Mob helped get them elected, and in some cases (Trump) were looked up to by the inhabitant of the Oval Office. Four Democrats and 3 Republicans come under scrutiny, so you can't say the author is biased.

If you want to know how crooked some of our leaders were and get an inside look at how the Mob influenced everything from legislation to major speeches, this is a book for you. If, on the other hand, you naively believe that all our leaders were fine, upstanding people with no warts, there's plenty of fiction out there for you to read.

This is obviously directed not just at those who are interested in the machinations of the Mob, but for those who are curious about the true inner workings of the man in the Oval Office. It's a fascinating read and an eye-opener.

[Charles Inglin · Rating 4 out of 5]

An entertaining, if slightly depressing, look at how organized crime has interacted with presidents, from FDR to the present occupant. Depressing because of the reality that the Mafia has money and influence through their infiltration of labor unions and businesses and that politicians need money and influence to win election. But also somewhat reassuring in that the extent to which the mafia has been able to influence presidents isn't that great overall. Lots of good stories, like how Joe Kennedy used his connections with the Mafia, through Frank Sinatra, to help get JFK elected, but then AG Robert Kennedy continued to go after the Mafia, causing at least one Mafioso to considering having Sinatra whacked. Another good story the author uncovered, the Mafia's involvement in solving the murders of the three civil rights workers in Mississippi. LBJ came down hard on J. Edgar Hoover, whose agents were having little success in breaking the Klan code of silence, to solve the case. Hoover, probably without LBJ's knowledge, allegedly turned to a psychopathic Mafia thug to break the case using means the FBI didn't want to know about. In return the thug received what amounted to a get out of jail free card for the rest of his life. A good read for crime fans.

[Kenny Schwarz · Rating 5 out of 5]

A very unique and fascinating look at some previous administrations and their Mob ties, some of whom directly benefitted from these connections (even if these Presidents later enacted anti-mafia policies, such as RICO law creation and aggressive LCN prosecutions).

It’s clear that the author is not a fan of the current President, as there are a few subtle biting references to Trump prior to the chapter on him. However the book is fairly well-balanced ideologically with detailed assessments of some of the most prolific presidents over the past 80 years or so. Even if some of them, Biden especially, seem to get a generous light touch.

As someone who is fascinated both by books in the mafia and on the presidency, this book was perfect for me! I found it fascinating and definitely recommend it.

[Liz P · Rating 4 out of 5]

This was a thorough and unbiased look at the connections between mob life and bureaucratic strategy. It’s never really been a secret the two have been intertwined to any American history buff but it was interesting to see it laid out in such an academic way while still remaining entertaining. We think of mobsters as these Tony Montana, Don Corleone, Al Capone type characters and the government as a bunch of Costner’s Elliot Ness’s but reality is so much more nuanced. This book touched on those nuances without falsely vilifying or glorifying either party.

[WM D. · Rating 4 out of 5]

As a frequent reader of political and true crime books. This book in my opinion was considered very good and very eye opening. It took the reader in my opinion into the world of mob involvement in the office of the president. It started out with Roosevelt and ended with Biden.

[Nancy G · Rating 3 out of 5]

The factual information faded into the background due to too much interpretation. I felt as if I was listening to the news through the spin of the commentator. To Dezenhall's credit, this is the comment he made in his author's note. The book is worth skimming.

[Deity World · Rating 5 out of 5]

Having studied USA 1920s followed by 1960s was interested to read this full of facts from organised crime to the watergate scandal a must read

[John Yingling · Rating 3 out of 5]

3.5 stars

[Lori Mitchell Myers · Rating 5 out of 5]

I hated history in high school!! But now, I can't get enough of stuff like this

[J. · Rating 4 out of 5]

**Prepare to be shocked! *Gangsters vs. Presidents* pulls back the curtain on the unholy alliance between the highest office in the land and the ruthless world of organized crime. This explosive exposé reveals how presidents, from FDR to Biden, have secretly leaned on the mob for everything from silencing rivals to influencing elections. Forget the history books – this is the real story of power, corruption, and the dangerous games played in the shadows where the White House and the underworld collide!**

[Toniann Churches · Rating 4 out of 5]

Tons of history I just didn't know. I love the way this book covers the different president's by chapter: FDR, Harry Truman, JFK, LBJ, Richard Nixon, Ronald Reagan, Donald Trump & Joe Biden. The read itself was slow but the information was mind blowing 🤯.

[Greg Giles · Rating 2 out of 5]

Dezenhall is a good researcher and can put together a hell of a sentence. He has more difficulty putting together a good paragraph, and even more a full chapter. A more forceful editor would have turned this into a must-read.

[Dan Petrick · Rating 5 out of 5]

4.8... a delight for history buffs

[Bob Manning · Rating 3 out of 5]

This is an expose on presidents that were involved with the Mafia. It was a lot more than I realized. It also debunked some of the myths.

[Beth Stowell · Rating 4 out of 5]

I won this off Goodreads. It was an enjoyable, true crime about presidents and their individual links to gangsters.

[Tony. AKA. Dad · Rating 5 out of 5]

This is a wow book crazy information. I never knew before slow but great read.

[Barbara · Rating 4 out of 5]

Fantastic book telling the history between the Mafia and the Oval office. The author goes into great detail outlining the history of the Mafia and how they influenced and helped the government. Well researched and lots of information that I wasn't aware of.

Gave this a 4 because the chapters on FDR and JFK were too long. Felt some stories were repeated. Would have liked to seen a note on why the other Presidents (Eisenhower, Carter, both Bushes, Clinton and Obama) were not included.

Recommend this book for those who are fascinated with the Mafia.

Thank you to Harper Collins thru the Goodreads giveaway for the advanced copy.

[Mimi · Rating 3 out of 5]

Connecting U.S. mafia history to United States presidents from the 1920s to the present and how the U.S. government benefits from them and occasionally acts like a mafia to get what it wants.
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This isn't a bad book, and it's extremely informative when it comes to how the U.S. government and the U.S. based mafias intersects and cooperated at times throughout history. However, this book reads like it expects you to already know a lot about the mafias and U.S. presidents. It reads like an argumentative paper where you're expected to have already done the readings to understand the connections the writer's making. It's not bad and makes good points but it can be hard to follow if you don't have a working knowledge of presidents and mafias which I didn't but I got the points/connections Dezenhall was trying to make.

I thought it was so interesting how much the U.S. government had used mafias over the years, and how after they used them, they hunted them down regardless if they helped.

I thought it was fascinating how they were used during the Civil Rights movement and how even though the mobster was extremely racist he still tortured a KKK member to help find missing murdered civil rights activists in the South.
I also didn't know about the Kennedy family's connection to the mafia or how connected other presidents were. It's so interesting how tied up the mafia was in the labor movement and working class politics, it makes sense but still so fascinating.

It's an interesting book, but if I didn't already have background knowledge about U.S. presidents, U.S. History and politics I might've been totally lost. I think this book might work best as a supplementary book whenever you read about mafia history in the U.S. I need to find that kinda book because I think I've had the wrong idea about mafias and I want to learn more.