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Theodore and Woodrow: How Two American Presidents Destroyed Constitutional Freedom

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A harsh and revealing political expose of two beloved presidents. Judge Andrew P. Napolitano reveals how Roosevelt, a bully, and Wilson, a constitutional scholar, each pushed aside the Constitution's restrictions on the federal government and used it as an instrument to redistribute wealth, regulate personal behavior, and enrich the government. These two men and the Progressives that supported them have brought us, among other things:

-the income tax
-the Federal Reserve
-compulsory, state-prescribed education
-the destruction of state sovereignty
-the rise of Jim Crow and military conscription
-prohibition and war

This Progressive Era witnessed the most dramatic peaceful shift of power from persons and from the states to a new and permanent federal bureaucracy in all of American history.

320 pages, Hardcover

First published October 16, 2012

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About the author

Andrew P. Napolitano

19 books145 followers
Andrew Paolo Napolitano is a former New Jersey Superior Court Judge. He is a political and senior judicial analyst for Fox News Channel, commenting on legal news and trials. Napolitano started on the channel in 1998. He is a Libertarian and a strong advocate of the Constitution, viewing it as a contract that must, according to rule of law, be interpreted the way its authors intended or else be invalid. He therefore asserts that the Federal government has a very limited set of powers, that it is exceeding, and that the Bill of Rights limits its valid actions in all circumstances.

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Displaying 1 - 30 of 67 reviews
Profile Image for Manny.
300 reviews30 followers
December 15, 2012
As is expected, the judge has produced another gem in his Constitutional treasure chest of books. This book covers the destructive era of "progressivism" and how it has left a stain on our history and quite honestly on our present and future.

I found the chapter on the 17th Amendment extremely interesting and enlightening. I have always wondered why the 17th amendment was ratified.

In this book, he discusses many of the mistakes the US made in regards to foreign affairs. Empire building has been one of the costliest, most destructive behavior in both blood and treasure, not to mention the hatred against us by the receiving countries. Napolitano also talks about race and how racist the progressive forefathers were. Ironically, today these men are lauded by the African-Americans in this country. It is akin to Stockholm Syndrome in many ways.

Napolitano discusses the dichotomy of the Lincoln era's conscription which is slavery by another name, in order to supposedly abolish slavery. Later this seed by the "Grate[sic] Emancipator" has allowed for the leviathan to grow out of control and interpret the Constitutions in ways never though of.

Equally interesting is the chapter on the Antiquities Act of 1906 and how the Federal Leviathan has used it to steal thousands upon thousands of acres from the states.

This book does what all Napolitano's books do; they open your eyes regardless of party. You see things for what they were from a Constitutional perspective. You may not agree with his conclusions, but the information presented are factual. You can choose to ignore them if you so choose.

The postscript of this book regarding the Supreme Court Ruling on "Obama-Care" is exceptional.

If Napolitano ran for office, I would do everything in my power to get him elected. He calls them as he sees them. Good, bad or indifferent. I have much respect for him. Hope you enjoy the book.
Profile Image for Wilson Hines.
61 reviews4 followers
November 27, 2013
The best way to describe the book is "wow!" How many times have you read a book and wanted your family, friends, and peers to read it? This is one of those books. From childhood throughout college, we have been taught to see T.R. as the consummate "Man's man," a man of the outdoors, a conservationists before being a tree hugger was cool, a man who stood up to Congress and "Big Business" in the place of the common man - a man who truly spoke for the common man.

The truth is very different. It is not what a man does, but why and how he does it that truly matters.

Roosevelt made several unashamed comments that absolutely upended and undermined the Constitution. He was a blatant power grabber and like Bill Clinton, he never had earned an income from anything other than inherited wealth or an appointed or elected government job or position. He honestly didn't understand the value in the Constitution, therefore he saw it as an impediment. He blatantly "went after" the constitution on many occasions without any regard for the circumstances. He actually made several statement like Obama has, whereas he would literally say publicly that the Constitution was impeding his power or his progress.

Woodrow Wilson was a bigoted Constitutional lawyer with an Ivey League education. He knew exactly what he was doing when he immediately lobbied for the 17th Amendment (the direct public election of Senators) and the rest of his disastrous Amendments. More Amendments to the Constitution happened during the watch of this man than several of those before and after him. He literally was intent on changing the face of the Constitution. From the Income Tax, which the whole purpose of made Prohibition Amendment possible, to Direct Election of Senators which officially ended the Federal system in the United States, to Prohibition, he cut the Constitution up from one end to the next.

I always wondered exactly how the 17th Amendment effected our country. I had my suspicions, but this book firmly answered those suspicions as fact and not conspiracy. The direct election of Senators absolutely tore the fabric of our country in a fundamental spirit. It ripped any power which the States had out of their hands and set forth a 100 year tradition of grid lock. It empowered the Executive more than any other branch (ironically), but it made a Senator almost impossible to be ejected. The idea our Fathers had was that the House of Representatives represented the people and the States were represented by the Senate, thus (for example) the main reason a treaty had to be signed by the Senate because a treaty was representing the will of the States, not the people. When you took the voice of the State out of national politics, you gutted the very essence of the system and transformed it into something very different and dangerous.

The 17th Amendment alone can be directly blamed for probably 80% of the stupidity in Washington DC today. Napolitano dedicates a chapter to this and does a marvelous job of explaining it.

The only down side to this book is that you can see he brings his religious zealously for Catholicism into the mix. While I understand that Protestantism has had it's fair share of stupidity, he seems to blame certain things in the Progressive Era on Protestantism unnecessarily. Somethings are valid, like Prohibition, but others aren't grounded in reality and his lack of footnotes in this area is a clue.

This book should be required reading to Juniors in high school.
Profile Image for Jeff.
78 reviews
January 13, 2013
"Judge Andrew P. Napolitano reveals how Teddy Roosevelt, a bully, and Woodrow Wilson, a constitutional scholar, each pushed aside the Constitution's restrictions on the federal government and used it as an instrument to redistribute wealth, regulate personal behavior, and enrich the government. These two men and the Progressives who supported them have brought us, among other things: -the income tax -the Federal Reserve -compulsory, state-prescribed education -the destruction of state sovereignty -the rise of Jim Crow and military conscription -prohibition and war

The Progressive Era witnessed the most dramatic peaceful shift of power from persons and from the states to a new and permanent federal bureaucracy in all of American history."
Profile Image for Ray.
1,064 reviews56 followers
May 21, 2013
Andrew Napolitano's main point(s) in "Theodore and Woodrow" seemed to be that the bulk of today's "big Government" woes can be traced back to the progressive policies and programs implemented over 100 years ago by the likes of Theodore Roosevelt and Woodrow Wilson. I thought that was an interesting point, and was curious, upon picking up the book, why he thought that was true. Unfortunately, Napolitano let me down in proving the main points of his case.

If you write a book on that topic, you can't get lazy and just say those things. I might assume some of his readers already are believers, so what he says may well resonate with their beliefs and his points might be taken at face value. When people have a strong emotional attachment to their initial convictions, they tend to ridicule anything that runs counter to those convictions, and to give a lot of weight to anything that supports them. So I think a truly good book will try to reach individuals on both sides of any argument, and the author has an obligation to do more than simply preach to the choir, and needs to explain to the uninitiated why his points are valid. That was the weakness I sensed in the book.

For example, he tells us that it was Theodore Roosevelt (T.R.) who turned the Country away from the non-interventionist philosophy of our Founding Fathers, and put us on the path (through the Spanish American War) to becoming global interventionists and the world's policemen. While I agree that T.R. and Wilson did much to reverse our isolationist policies, it's hard to fully buy into the argument that it all began with T.R. The Spanish American War, and the annexation of Hawaii, both were new examples of foreign involvement from that era, but both took place before either of their presidencies. But even if Napolitano's assertion is true, does that mean that we're stuck with that same philosophy to the present day? Should that mean that subsequent Administrations can't limit that philosophy? If not, then the implication is that Napolitano, as a Conservative / Libertarian, is simply making poorly thought out arguments against anyone called "progressive".

An expansionist foreign policy from 100 years ago isn't like some Supreme Court president-setting decision. Policies can, and do, change. I can't imagine President G.W. Bush, Dick Cheney, and Donald Rumsfeld sitting around the Oval office saying they really didn't want to take out Saddam Hussein in Iraq, or the Taliban in Afghanistan, but their hands were tied because they had to follow the interventionist policies of those progressive presidents from 100 years ago. If someone yearns for the isolationist days of our Founding Fathers, it just didn't seem logical to say it's all the fault of the Progressive movement, especially since the initiating event he points to, the Spanish American War, began before either of the men began their presidency.

There are a number of other assertions which Napolitano listed in his book which I didn't fully buy into, and I've listed several of those below for anyone who may be interested. But I felt that Napolitano, having Conservative and / or a Libertarian leanings, didn't do enough to make his points, and simply blamed things he didn't like in Government today on a couple of presidents from the past whose philosophies were contrary to his own. There was no real recognition of how the world changed and would have changed with or without the actions of these two presidents, and how complex the actions and policy changes he referred to actually are. He puts the blame on these presidents, but doesn't address how many of these very changes are Congressional actions, not presidential decrees, and that Congress is at least as responsive to the people, the press, and the party, if not more so, than to the President.

I tend to think that money talks, and as much as Napolitano might want to blame progressives for big government of today, you have to wonder what keeps it big. I thought it was interesting to note that last month, when I first picked up this book, that special interest groups having legislative issues pending in the 113th Congress were especially active with big contributions. Political Action Groups making big contributions to federal candidates and committees in April included the Letter Carriers Political Education PAC, topping the chart with over a quarter million dollars. How might that influence Congressional votes to reduce Post Office spending? Other big contributors giving over $150,000 last month, in addition to the postal workers, were defense firms like Boeing, Northrop Grumman, and Raytheon, sugar farmers, communications companies like Comcast & NBC, and insurance / financial firms like the Council of Insurance Agents & Brokers, Independent Bankers of America, and Koch Industries. To me, that's what moves the government of today, not the legacy of two presidents from 100 years ago.

(Anything I've written below is just an embellishment of the above. It's more my initial thoughts, more for myself than for anyone else, and even I wouldn't recommend reading the rest of my review).
I felt the book's limitation was that Napolitano didn't do enough to convince the reader that the alternative small government philosophy is the better choice. He was critical of T.R. and Wilson for their Progressive philosophies, and their expansion of government involvement and programs, but many of those changes were inevitable anyway, and Countries which haven't yet adopted those "progressive" changes which he mentions, such as child-labor laws, voting rights for women, an educational system for all children, are those countries we consider backward today, and those are the third world countries which we criticize today for their lack of progress human-rights deficiencies.

Another current government program which Napolitano criticizes is the Federal Income Tax law. That's an easy target. We all complain about Federal Income Taxes, but most Countries have income taxes now, and they were inevitable. In the days of our Founding Fathers, which Napolitano refers to, federal income came mostly from tariffs and import duties. That was enough for the simple society which existed. There was no need for modern programs like a Food and Drug Administration, since people grew their own food and raised their own domestic animals, or traded with the neighbors they knew for what they needed. But times inevitably change, and no one I personally know today goes out to their back yard to grab a few fresh eggs from the chicken coop each morning, nor slaughters their own pig for their bacon, ham, or pork chops. Society evolved, for most of us, we no longer know just where our food comes from, nor how it's processed. So while not necessarily a universal need, as a city dweller, I don't mind having someone looking out for my own good when it comes to the food I consume, the water I drink, and the medicine I take. So perhaps the expansionist ideas of T.R. or Wilson planted the seeds for a Government program like the Food and Drug Administration, but I think I'd rather live in a place with some controls than without. Perhaps this can be considered "... another government intrusion on our liberty...", but personally, I prefer wholesome (safe) foods, water, and medicines, and don't trust that unregulated businesses will compete safely in an unregulated market without some regulations and oversight.

Napolitano also laments government intrusion into our educational system. Again, he argues that government intrusion into our schools is an intrusion of our liberty, and there's plenty to complain about when looking at our educational system. However we can't all home-school our children. The alternative to requiring 100% of our children attending school is to have higher illiteracy, a common problem in poorly developed countries. And again, I like living in a Country of (mostly) educated and literate people which helps foster innovation, productivity, and a higher standard of living.

In addition to the above, Napolitano also included a wide range of other government "problems" which he traced back to T.R. and Wilson. Perhaps the Environmental Protection Administration (EPA) doesn't get everything right, and perhaps the EPA represents "too much government", but it was established during the Nixon Administration in the 1970's, and to link it to Teddy Roosevelt is a leap in logic. Napolitano also didn't like the 17th Amendment (direct election of our Federal Senators), since it represents, to him, a taking away of State's voice in Government, but I didn't follow his argument, nor understand why individual States approving the Amendment becomes the fault of these two Progressive Presidents.

So I didn't fully agree with the idea that everything these progressive presidents pushed for were bad for the Country. I do believe, as he does, that the Government is too big, that we waste too much money on programs that don't work, which aren't needed, or are counter productive. But Napolitano made a large leap in logic to simply imply that all these ills are the natural product of these two presidents and their policies, and that reversing their programs and eliminating government from our lives will make everything better.

In spite of the book's title, "Theodore and Woodrow" wasn't meant to be a biography of either President, but rather it was intended to represent a case AGAINST them. According to Napolitano, both TR and Wilson, by their progressive policies, altered the relationship of government to individuals in America. And, as he argued, this did not make us more free or prosperous, but rather set us on a course for massive government. Too often, Napolitano seemed to think branding these two Presidents as "Progressives" was enough to demonstrate that anything "wrong" with the Country over the next 100 plus years was a result of their legacy. That was quite a reach, in my mind.

As I already mentioned above, Napolitano stated that the intent of the Founding Fathers was to keep the Country focused internally and avoid foreign entanglements. He then asks how and when we varied from that path of the Founding Fathers, and answers that it began with Theodore Roosevelt and the Spanish American War of 1898. While recognizing that the book is intended to be critical of T.R., I felt this specific criticism was more than a reach. T.R. was only Assistant Secretary of the Navy at the time hostilities broke out, and it's really hard for me to attribute the turn around of U.S. involvement in international affairs to the Assistant Secretary of the Navy. That position just doesn't have the power to influence U.S. policy to that extent, and I thought Napolitano was losing credibility and trying too hard to blame too much of today's woes on T.R., simply because he can be labeled as a Progressive. Additionally, by that time, the U.S. had assisted in the overthrow of the Hawaiian monarchy and had annexed Hawaii in support of U.S. business interests, evidence of foreign involvement well before the Progressive presidency of either Roosevelt or Wilson.

At the risk of being too repetitive, Napolitano attributes our current federal income tax laws, which no one is going to like, as a legacy of Teddy Roosevelt. However, even as he mentions, the Income Tax was first established during the Civil War, when Roosevelt was only four years old. So no matter your political leanings, and any desire to attribute everything "bad" to progressives, this seemed to be yet another illogical leap in logic. It is true, I believe, that Roosevelt did support the 16th Amendment establishing the Income Tax, but it was hardly instituted because of him.

This isn't to say that I find fault with Napolitano's criticism of T.R.'s pushing the envelope to expand American influence and scope. To Napolitano, T.R. considered the Constitution just a "guideline", a definite fault to any strict constructionalist of the Constitution. Roosevelt did support a number of other changes in his unsuccessful 1912 Bull Moose Progressive Party platform, which called for women's suffrage, an inheritance tax, workman's compensation, a Federal Securities commission, farm subsidies, worker's rights, including an 8-hour day and minimum wages for women, and a national health service. These things have all come to pass, so had Napolitano stayed strictly with items such as these, and made his argument as to why these ideas are harmful to the Country, his book would have had more credibility.
Profile Image for Diane Kennicker.
67 reviews1 follower
January 2, 2014
Excellent read. The author outlines how the "Progressives", Theodore Roosevelt and Woodrow Wilson, did much to destroy the constitutional freedoms and liberties our Founders intended for us to enjoy. It's clear that their successors and the elected officials have perpetuated the stifling of our liberties. Anyone who is disgusted with our present day politics should review the damage Theodore and Woodrow did in their time and how we still live with those consequences.
The Progressive movement isn't progress at all - it's a way to control and suppress the populace.
Profile Image for Kym Robinson.
Author 7 books24 followers
May 31, 2017
The Judge is always very easy to read, he has an ability to write in a way that keeps you moving while also making his point and often you will learn something as well. This book is no exception. The Judge delves into the uncomfortable facts of great moments and men and expose them for what they are. Ugly and human.

In 'Theodore and Woodrow' the Judge seeks to prove that these two presidents of the USA are responsible for much of the ills of modern American and international life. He depicts them both as the despots that they were, but goes so far as to suggest that they have inspired and validated subsequent US presidents in their over reach of constitutional powers.

While Presidents Wilson and Teddy Roosevelt were ugly men of history, despite the many official adulation's that are awarded to them. It is in my opinion a stretch to so simply presume that without these over glorified tyrants that no other American president would not also be instinctual in their urges to control, rule and murder in the name of legacy or ideology. Regardless, the Judge does expose both men as the Imperial presidents that they were. But were they the only key villains in American political history?

Just as many of those that adore men like Wilson and Roosevelt romance them and hold them with mythic esteem. I fear that the Judge has the same romantic illusions about the 'founding fathers' and the constitution. And despite his valid criticisms of Teddy and Woodrow one could just as easily, perhaps on a far lesser scale, direct these critiques to prior presidents who over saw mass human bondage, near genocide, war, imperialism and so on. Not to mention the flaw in holding a near reverence for a constitution that has perhaps never been obeyed or adhered to by ANY of its executive or legislative officials.

Though I did enjoy this book and do agree with much of the criticism of these two men, I think that it is harmed by a need to 'blame' both progressives and these two rulers for subsequent US political oppression. It overlooks a prior history of American imperialism and cruelty that predates both Teddy, Woodrow and the progressives that thrived during their reigns. Such cynical and sinister beings were not the exceptions of history unfortunately.

This is a good book to read and does inspire many topics to further read up on, it is also a somewhat flawed book that reveals a confirmation bias on perhaps the part of the Judge and many of the liberty minded readers who already 'know' that Wilson and Roosevelt were baddies. Because of that it assumes a prior mindset. For the non-American reader without the luxury of a prior knowledge of American political royalty this book may be a hard read. Just as it may also come across as coarse for those who have been raised in a propaganda filled upbringing where these two men were glorious heroes of the Republic.

I do recommend this book and do score it highly, I just wish that it was done more as a history book and less of a need to link modern incidents to the two men. Certainly, they did write laws and affect change in a many way but outside of the limited spectrum of American-importantism one can see that Central banks occur despite a Wilson, that colonialism happens regardless of Teddy, racist bigotry goes beyond the duo or that aggressive interference in other nations has happened prior and beyond the American 'republic'. And regardless of the putrid progressives, such attitudes and policies happened outside the USA in some form or the other, much to the detriment of all the victims.

To assume that America is exceptional and special is both arrogant and limited. To assume that without these two rulers that Americans would not have gone down this path defies the opening days of America's own history. And to assume that other American rulers would not have engaged in further colonialism or a European war is perhaps true in some accounts but not absolutely certain as it seems that the one true democratic constant of the American exceptionalist self-perception is that they can never do wrong and that they are entitled to all that they take and do, regardless of how many corpses are left rotting. This is not merely reserved for the Roosevelt's or Wilson's but for the entire United States politico-military establishment and its many adoring voters both past and present.

Please read this book along with others on the subject. It is a good place to start for those wanting to understand this time in history. It is perhaps a fork in the road read for those who are already familiar with this period, from a certain perspective. Despite the books faults and clear direction, it has far more strengths.


Despite these issues with this book I still give it a 76% on my arbitrary scoring scale.
Profile Image for Jessie Gussman.
Author 320 books894 followers
November 11, 2015
I was expecting to like this much more than what I did. I agree 'that government is best which governs least', and Wilson and Roosevelt both oversaw huge increases in government power with the resulting loss of individual liberty. However, it was hard to separate Napolitano's opinion from plain facts. He used a lot of loaded words to push the reader into accepting his conclusions, and I'm sorry, but that irritated me. The biggest drawback of the book, though, was that Napolitano made so many assumptions of motivation for both Wilson and Roosevelt with no primary source documentation that I totally stopped believing anything he said unless it was endnoted. An example: "The president saw no reason to get any of them involved, given that he believed that he could easily work around them." If you're going to make a statement like that, give me some quotes from the president to back that up. Napolitano didn't. And he made statements like this throughout the book, not just about Wilson and Roosevelt, but about the motivations of others as well. How does he know? Maybe those statements are based in fact, but if he wants me to believe them, he needs to support his sweeping opinions with facts grounded in primary source documents. Those were completely absent from this work.

I'm not disagreeing with facts that were presented--both presidents violated the Constitution blatantly and with a shocking disregard for freedom and liberty and America is still reaping the consequences. However, I do believe good men can make poor decisions while believing that they are working for the 'greater good'. This book failed to convince me that these men were inherently evil and wicked.

There are truths in this book that you won't be taught in any public school or university, but I personally don't think it's necessary to assign your own motivations to people with whom you disagree.
Profile Image for Jared Lovell.
98 reviews16 followers
February 20, 2013
As Napolitano says at the outset, this is not meant to be a definitive biography of either Theodore Roosevelt or Woodrow Wilson, but rather a case against both of them. This is a much needed volume and an excellent start for those who are seeking to understand how radically transformative the Progressive era really was in American history. Napolitano covers every subject from education, to banking to taxation to prohibition and show the effects of these two Presidents on all of these areas. I think of most importance in this book is the topic of war. Napolitano goes into the ugly details behind the Spanish-American War and WWI and how these Theodore Roosevelt and Woodrow Wilson were instrumental in moving the nation from peaceful republic to bellicose empire. Napolitano has his usual blind spots when it comes to the explaining the role of the courts, but overall this is an excellent read and I recommend it!
Profile Image for Drtaxsacto.
703 reviews58 followers
March 11, 2015
This is an unfortunate book. The judge starts with a premise with which I agree - namely that TR and Wilson were not among the best presidents and further that current history has seemed to gloss over their foibles (like Wilson's racism). The problem with the book is that it goes on a series of rants that while they may be emotionally satisfying to extreme libertarians there is little to take anyone who is concerned about the size and scope of the federal government and begin to address how to change the situation.

Two of the chapters which bothered me the most were ones on the banking system - which completely misreads the history of the creation of the Federal Reserve (and I am not necessarily a fan) and on the income tax.

Did Wilson and TR enlarge the scope and size of the federal government through bluster and political skill - sure they did. But there are better books about both presidents which point out their foibles without resorting to polemics.
Profile Image for NVTony.
462 reviews2 followers
January 10, 2013
Bias of this retired Judge is showing. Always glad to see how current writers interprete actions of past leaders. Conspiracy theorist will find much support for some of their theories but be disappointed to learn author feels giving selection of Senators to voters was error.
Profile Image for Stanislav Siris.
9 reviews1 follower
May 29, 2017
This is an informative history book that shows how the two progressive Presidents, Democrat Woodrow Wilson and a Republican Theodore Roosevelt, have pushed for an ever increasing role of the federal government at the expense of liberty. More importantly, it shows that the two Presidents had no respect for the ideas and the reasons behind the Constitution and have been proponents of, and guided by, ideas of “living Constitution”.
However, while being informative, author also tries to put the blame squarely on the two Presidents, while not giving enough credits to progressive ideas being popular among people in general. Also, Judge Napolitano seems to equate the two Presidents to ruthless Soviet Union dictator, Joseph Stalin, on the basis of propaganda methods employed. That, in my opinion, is a bit going too far. Using the propaganda is one thing. Being in total control over the population via unchallenged violence is another and that Wilson and Roosevelt were not. Though, I have no doubt that greater control by the Federal government is something they would favor, given the chance.
Personally, this book made me see conscription for what it is, a forced labor. It also lead me to re-evaluate my views on how Bush administration handled the events of 9/11, though I disagree that oil or revenge were ever the motives. In this regard I tend to side with, less passionate, analysis by George Friedman, founder of Stratfor analytical agency, that supposes that Bush administration was simply trying to establish a puppet government that would be more “understanding” in allowing to use its territory, as opposed to other countries in the region.
All in all, I would recommend this book. It contains a lot of interesting historical facts and it certainly adds to one's knowledge base.
Profile Image for Kristel.
2,002 reviews49 followers
April 13, 2023
Reason Read: nonfiction book about someone you want to know more about, TIOLI April, ROOT
I bought this book in 2013 and finally I am reading it. I really enjoyed it and the audio book was good but this is a book that might be better to be able to read in tree form so that you can take notes and look up more information.
What I learned: it doesn't matter who you vote for, government and our two party system is all about grabbing power and taking away our freedoms.
In the medical field we consumers decided we did not want paternalism but as citizens of our country we willingly let government be paternalistic. Why do we do this? Why do we think the government really cares about anything but itself?
Roosevelt, a conservative, was a warmonger, conservationist and Wilson was a liberal who believed in population control (eugenics and other measures to control for poor, weak genetics), compulsory education to take away parents rights to children education (especially of the immigrants).
The book covered so much; racism, imperialism, compulsory education, government control over what we eat, creation of agencies that remove the citizen's right to have a say in government, Federal reserve bank, inflation, taxation.
Some things to look into; Dr. Harvey Wiley and the Pure Food and Drug Act, The Jungle was full of falsehoods and Sinclair did not care about the working man., Theory of a Living Constitution (scary), Birth of a Nation (Silent Film) second birth of the clansmen, Antiquities Act.
Profile Image for Dan.
Author 1 book4 followers
March 12, 2023
"Theodore and Woodrow" is an important book that really demonstrated how (apart from the slavery issue) constitutional rule and limited government in the United States really began to fall apart. It also completely changed my formerly positive view of Teddy Roosevelt.

So it's worth reading for that alone, but I offer two caveats:

(1) Napolitano appears to be a pure "natural law" thinker, ignoring completely the moral/spiritual health of the society. It's not clear to me whether he is expressing these views purely as a legal interpretive framework or as a broader philosophy of government. If the latter, the idea that the state has no responsibility at all to God is concerning to say the least.

(2) His discussion of U.S. foreign policy activism over the past 100 years completely ignores the international Communist plan for world domination during most of the same time period. He assumes all of those involved in U.S.-initiated coups were motivated entirely by nefarious motives, never once considering the nuclear threat and the Cold War competition for strategic resources and locations. There is still plenty to criticize even within that context, but to ignore such a major factor altogether was a glaring omission that undermines his entire argument against U.S. foreign policy in that period.
1 review
August 16, 2020
I found this book fascinating. At times the stories that the Judge described, scared me. This book tells of the belief systems of Theodore Roosevelt and Woodrow Wilson. Both were Presidents of the United States. Judge Napolitano shares with the readers how Presidents Rooseve!t and Wilson felt about the United States, her people, and the Nation's Constitution. I feel that I had a good education in high school and college. I have read a fair amount of history. I had no idea that these two presidents were responsible for the contradictions to the constitution that they were. Reading this book was interesting.

As our election approaches, take some time, and read this book. I highly recommend it!
Profile Image for Jason A. A..
Author 1 book1 follower
May 4, 2021
The author takes aim at both a Republican (Teddy Roosevelt) and a Democrat (Wilson) who were both as Progressive as it gets. He makes an intriguing argument that these two men together destroyed the American Republic. While I think it's clear that the actions of Lincoln and the Federal government during the Civil War actually shred the Constitution the most, it's difficult to disagree with his assertion that TR and WW finished the job.

I would encourage anyone interested in History or the Constitution to read this. It was written during the early Obama years but his arguments have only become more relevant with the happenings of the pandemic, lockdowns, and race issues.
Profile Image for Eric.
4,194 reviews34 followers
September 22, 2021
Should almost certainly be required reading for all Tea Party Patriots, although there will likely be a number of places where some conservative heroes do not come off so well. The entire work holds together quite well as a complete evisceration of the progressive movement's program of subjecting citizens to the federal leviathan. Perhaps its only shortcoming is in not prescribing correctives for the most egregious elements - for example, why might he not have advocated for repeal of the 17th amendment (direct election of senators) as one of them. I can only guess that this did not fit his (Napolitano's) narrative for this particular work.
Profile Image for James Stephen Lorson.
16 reviews
May 9, 2018
Outstanding and eye opening book. Well worth the time to read and understand how we have arrived at the mess we are in with our government. Details the destruction of our Constitution but does not give any ideas as to how to correct the problem. However, in my opinion, there is a key sentence in the founding documents, The Declaration of Indepencdence, which gives the answer. Go read and see.
Profile Image for Tim.
307 reviews
May 2, 2019
A fantastic book that details exactly how two long revered presidents used their power to twist the Constitution to their liking. Public schools that I attended and work in still seem to mostly teach the greatness of T.R. when it seems that he is not so great as much as he was maniacle. Any American who wants a better understanding of where we are today should read this book.
724 reviews3 followers
August 23, 2019
I didn't enjoy this which I knew would happen but it is good to be exposed to thoughts you don't agree with. Some of it was fine as he had the history correct, some of it was correct in the history but his conclusions were faulty, and some of it he just got wrong. He did get me thinking about stuff though so that's good.
180 reviews15 followers
July 6, 2016
“Theodore and Woodrow: How Two American Presidents Destroyed Constitutional Freedom” by Judge Andrew Napolitano is an entertaining read, but I was a bit disappointed relative to my initial expectations. Judge Nap is not the greatest writer out there, but he does a very good job at scaring and exciting the reader. I generally align politically with Napolitano, so I agree with the vast majority of what he writes in the book. At the same time, I do not believe he does a good enough job to convince people across the aisle that he is correct. I think anyone that reads this book will rightfully see Teddy Roosevelt and Woodrow Wilson in a different light than they had previously, assuming their previous knowledge of the two came from school or from progressive-leaning historians. However, I find his support of libertarian-leaning ideals to be under-supported in some instances throughout the book, which is a disservice if he wishes to convince readers with different political outlooks that he is correct.

Napolitano’s main premise is that the huge government in today’s America can be traced back to the ideologies and actions of Teddy Roosevelt and Woodrow Wilson, the presidents that brought in the American Progressive Era. Both Roosevelt and Wilson distrusted the judgment of the average person and believed that the government should step in to regulate behaviors, economic transactions, and employer-employee relationships. Also, they believed that the United States should be the world’s policemen and intervene in foreign affairs to increase American influence. There was more than a hint of racism in all of these policies; both men were extremely racist. The outgrowths of the Progressive Era, such as the FDA, IRS, and Federal Reserve, are still with us today. Subsequent presidents have followed in the steps of Roosevelt and Wilson to continue to expand government’s influence and expand America’s influence on the rest of the world. These two presidents had no regard for the Constitution and were able to circumvent it in seemingly countless ways. These presidential actions, accepted by courts as legal, serve as defense for unconstitutional presidential actions today. Napolitano does a good job to connect issues such as the War on Drugs, the PATRIOT Act, and chronic forest fires to policies promoted by Roosevelt and Wilson.

While I believe that our big government policies today have a lot in common with the visions of these two men, progressive policies did not begin with them. The United States had adopted a far more bellicose foreign policy position before Teddy Roosevelt’s rise to the presidency, so an interventionist United States was not a completely new phenomenon that arose solely under Roosevelt and Wilson. “Paternalistic” government policies could be traced back to Lincoln’s unconstitutional actions leading up to and during the Civil War, though some administrations (namely Grover Cleveland’s) beat back the expanse of federal government power before finally losing that battle during the Progressive Era. Napolitano mentions Lincoln several times, pointing at his disregard for the Constitution, but I believe he could have done a better job explaining the lead-up to the Roosevelt and Wilson presidencies and connection their ideas to the Lincoln presidency. These two men did not operate in a vacuum, as there was already widespread support for increased food regulation, the income tax, an adventurous military, and hostile actions toward “trusts”. All that was needed were two men without regard for the Constitution that could bull their way through constitutional limits to bring these ideas to fruition.

Napolitano is always entertaining, so I enjoyed the read. I liked “Theodore and Woodrow” because it exposes two of the worst presidents in American history. I think it had the potential to be much more informative, but I believe that it would be very difficult for anyone to read this book and still believe that these men were good presidents. He seems murky on Austrian economics and on economics in general, so do not expect too much in that department. I remember one instance where he said the “marginal” tax bracket is synonymous with the tax rate in the highest tax bracket, but this is not true. The top marginal tax rate is synonymous with the rate paid by incomes within the highest tax rates, but all of the rates in the various tax brackets are marginal. I also believe that he was calling deposits held at a bank an asset of the bank, rather than a liability. I read and reread what he wrote, and I cannot see another way to interpret this apparent mistake. He has a tendency to intertwine fact with opinion without clearly separating the two. Also, he will quote from “sources” that were simply giving their opinions without clearly stating that the quote represents someone else’s opinions. Anyway, though, he is great at what he knows, and in this case that is the Constitution. He explains Supreme Court cases in extremely accessible terms and relates them well to the wording of the Constitution and the debates surrounding the ratification of the Constitution. He is great at dismantling those with whom he disagrees, and “Theodore and Woodrow” is no different.
Profile Image for David Sheedy.
62 reviews
March 24, 2018
It was a well written book but I feel that a lot of his conclusions very broad and, I do not agree with a lot of his conclusions regarding United States participation in the great war, and the long term world impact of that participation.
Profile Image for Claire Binkley.
2,283 reviews17 followers
July 25, 2020
Gosh, I felt rather quite guilty reading this book since I couldn't remember exactly the other book it reminded me of, so I got rid of it as soon as I could - what these two Presidents did was super-important to something I really like to read and consider, though.
Profile Image for James.
176 reviews
June 6, 2017
He got a bit preachy about half way through and lost his message.
306 reviews7 followers
December 5, 2017
I used the audio version. This is a pretty well done production. The book is more a political and social analysis than a biography. More a light hearted fun read.
Profile Image for Nick.
133 reviews2 followers
August 14, 2021
This was a different take on Wilson & Teddy, their role in the rise of the progressive movement.
Profile Image for Jessica Harvey.
202 reviews1 follower
May 26, 2025
This book lays blame to the progressive movement for giving unlimited power to our government. It was the works of Theodore Roosevelt and Woodrow Wilson that made it the president's responsibility to step in to stop a regulatory agency from promoting regulations that Congress refused to enact. In this way, enumerated powers as defined by the constitution have less power over the people in Judge Andrew Napolitano's professional opinion. This gives more power to a president who is unconstitutional in office to prosper.
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484 reviews29 followers
August 31, 2014
Ever since Judge Napolitano went on John Stossel's show, I've been a huge, huge fan. His understanding of the law and Constitution is, sadly, a breath of fresh air. In this book it was interesting to see that Napolitano looks at the then history of Theodore and Woodrow but also shows what outcomes came from their actions - even those leading up to today. This book isn't highly technical. It's not a 500 page indepth study of the two men. That is up the reader. Napolitano makes his case that the two men were as close to dictators that this country had and the policies they wrought still have lasting consequences. The best thing about this book is the sound, logical, and Constitutionally pointed to arguements that Napolitano is an expert at making. He really is a joy to read (and listen to when he's on TV). The one downside to this book is that in the middle when talking about the war lust of the men, especially Theodore, it tends to get bogged down in history more than anything. I understand the points he's making and why he's giving the history, but it was a little slow around those parts. He also tends to sight in on Theodore more than Woodrow. Again, I can see why but if you wanted to learn more about Woodrow then you may be disappointed. I'm not sure how someone on the other side of the isle would say about this book - on whether it makes fair accusations. I think he does a fair job. After reading James Bradley's "The Imperial Cruise". I think Napolitano characterizes Theodore especially right on. If you're a fan of limited governemtn, the Constitution, and a honest critique of two Presidents that you learned about in school that were oh so great and awesome men - check this book out. Final Grade - A
4 reviews
December 10, 2016
Those who should read: Anyone who already hates big government looking for more talking points to belligerently toss around comment boards and angry social media rants. Also, those who do not require intellectual justification for what they believe and who do not believe in nuanced ideas or the complexity of history.
Those who should not read: Anyone interested in engaging other intelligent beings in convincing debate. Also those who enjoy thoroughly supported and well reasoned arguments.

For a book whose thesis and main points I tend to agree with more often than not I was astonishingly disappointed with the author throughout most of this book. Unfortunately, what could have been a compelling narrative with great potential for explaining much about the course of the last century's political evolution falls far short of even making a coherent argument. Accusations of evil intent are casually thrown at Roosevelt and Wilson, but justifications for these accusations are few and far between. These vague attempts do little except squander the opportunity to engage readers in a timely discussion about the proper authority of the federal government. Contradictions are common and are passed off so casually as to make the reader wonder if the author is aware of the conflicts within his text or if he is actually so ideologically vapid that he hasn't even noticed his own contradictions. The author can't seem to decide if big businessmen of the progressive era are heroes worthy of Atlas Shrugged or dastardly collaborators complicit in the reckless expansion of the federal government. This subject is worthy of exploration and the thesis of the book isn't without merit. However, this book does not satisfy the demands of coherent argumentation or basic academic investigation.
106 reviews11 followers
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February 17, 2017
Very, very good. Insightful history. The Judge hit out of the park. However, it's also very depressing and disgusting when you see exactly how corrupt and self-serving politicians are. We know these things but the way Napolitano spells it out makes us realize how limited our awareness and understanding is.
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