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Theodore Roosevelt and the Making of American Leadership
This is the story of perhaps the greatest leadership journey in American history.
President Theodore Roosevelt forever transformed America, ushering the country into the arena of world supremacy. His brand of leadership was entirely confident,compassionate, energetic, diverse, visionary.
But Roosevelt was not a born leader; his ascent to the apex of power was not a foregone conclusion. He made himself a leader of consequence, and it is his epic journey to the White House --a road filled with terrific failures, intimate introspection, and self-made luck--that will inspire readers anew. No author has combined his key biographical milestones--the lessons born from the contradictions of his life--with the surviving stories from those who followed and interacted with him in his various attempts to lead.
While a graduate student at Harvard, author Jon Knokey , a Roosevelt historian and business leader,unearthed hundreds of unpublished letters and interview notes from Roosevelt contemporaries. These long-forgotten documents provide a fresh and stunning ringside seat along the twenty-sixth president's journey to 1600 Pennsylvania Avenue. The stories from Harvard chaps, idealistic political reformers from New York, coarse cowboys from the Badlands, and tough-as-rawhide Rough Riders from the nation's interior all combine to illuminate the maturation process of a man learning to lead at every stage of his life.
The story of Theodore Roosevelt's life has been told before. The story of his leadership journey has not--until now. Fast-paced and written as a biographical narrative, Theodore Roosevelt and the Making of American Leadership places the reader alongside a young Roosevelt as he shapes events, people, and himself to forever change a country. He created an authentic style of American leadership--a style that has endured for over a century.
President Theodore Roosevelt forever transformed America, ushering the country into the arena of world supremacy. His brand of leadership was entirely confident,compassionate, energetic, diverse, visionary.
But Roosevelt was not a born leader; his ascent to the apex of power was not a foregone conclusion. He made himself a leader of consequence, and it is his epic journey to the White House --a road filled with terrific failures, intimate introspection, and self-made luck--that will inspire readers anew. No author has combined his key biographical milestones--the lessons born from the contradictions of his life--with the surviving stories from those who followed and interacted with him in his various attempts to lead.
While a graduate student at Harvard, author Jon Knokey , a Roosevelt historian and business leader,unearthed hundreds of unpublished letters and interview notes from Roosevelt contemporaries. These long-forgotten documents provide a fresh and stunning ringside seat along the twenty-sixth president's journey to 1600 Pennsylvania Avenue. The stories from Harvard chaps, idealistic political reformers from New York, coarse cowboys from the Badlands, and tough-as-rawhide Rough Riders from the nation's interior all combine to illuminate the maturation process of a man learning to lead at every stage of his life.
The story of Theodore Roosevelt's life has been told before. The story of his leadership journey has not--until now. Fast-paced and written as a biographical narrative, Theodore Roosevelt and the Making of American Leadership places the reader alongside a young Roosevelt as he shapes events, people, and himself to forever change a country. He created an authentic style of American leadership--a style that has endured for over a century.
512 pages, Hardcover
First published October 27, 2015
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487 people want to read
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September 24, 2023
― “By his thirtieth birthday, Theodore Roosevelt thought of himself as a great man. His life experiences had vindicated to him that he was a survivor, physically and emotionally. He knew that his values and principles had been tested under pressure, and he gained strength from meeting those challenges. All of his intense tribulations and experiences, packed into such a short time frame, had crystallized who he was.”
― Jon Knokey, Theodore Roosevelt and the Making of American Leadership
Theordore Roosevelt remains one of America’s most remarkable presidents, and with good reason. His personality and achievements make him unforgettable. He is often considered the first modern President because he significantly expanded the influence and power of the executive office. Surveys of historians and political scientists over the past decade have rated him the fourth best president, behind only George Washington, Franklin Delano Roosevelt, and Abraham Lincoln. The story of how Theodore Roosevelt became President is worthy of our attention. Perhaps that is why this makes the eighth book I have read about the 26th President of the United States, including Edmund Morris’s excellent three-volume biography.
In his first book, Theodore Roosevelt and the Making of American Leadership, author Jon Knokey has chosen to focus on the development of Roosevelt’s leadership skills. To understand the leadership of Theodore Roosevelt, one must understand a little of his dynamic and fascinating story of his life. Teddy Roosevelt was certainly no leader as a child or during his college years at Harvard. Theodore was born into one of the wealthiest families in New York. His father was a descendant of Dutch merchants who made their fortunes in one of the most prosperous ports in America. His mother was descended from the southern aristocracy. As the son of a wealthy family, Theodore could have led a life of privilege and leisure. But, as a child, Teddy was undersized and sickly. He struggled with severe asthma and poor eyesight. Roosevelt spent most of his early childhood indoors while his siblings played outside. During this time, he developed a love of reading books from his father's library. Seeing that his son had a mind, his father told him he must make his body. To improve his health, he boxed and lifted dumbbells in a room his father had converted into a gymnasium. TR would go on to be an exponent of “the strenuous life.”
― “His father’s challenge was integral to the origin of Theodore Roosevelt’s remarkable courage and fighting spirit.”
― Jon Knokey, Theodore Roosevelt and the Making of American Leadership
When his wife and mother died on the same day, Valentine’s Day 1884, Roosevelt penned, “The light has gone out of my life.” He left his daughter in the care of his sister and went to North Dakota, where he spent two years ranching and dealing with his grief. Yet it was in this cauldron of grief and strenuous living where Theodore Roosevelt first demonstrated leadership skills.
― “Roosevelt’s time in the Badlands was also, unquestionably, the most influential period in his leadership development. … The experience took the elitist out of him.”
― Jon Knokey, Theodore Roosevelt and the Making of American Leadership
Roosevelt began his life in politics as an elected member of the New York State House, then served as the New York City Police Commissioner. He then went on to do serve as the Assistant Secretary of the Navy. When the Spanish-American War broke out, he was commissioned as a Colonel in the Army. Leading a group of volunteer soldiers known as the Rough Riders to a significant victory at the battle of San Juan Hill, Theodore Roosevelt became a national hero.
Most of the second half of the book is devoted to the story of Theodore Roosevelt and the Rough Riders. When the “Rough Riders” first met Roosevelt, they weren’t particularly impressed with this bespectacled man from the East. In time, he earned their respect, love and devotion.
― “Galloping back and forth, Roosevelt began to shout, ‘Men, we must advance! Rough Riders Forward, Come On!’ The distinction between ‘Come on!’ and ‘Go on!’ was not lost on the men.’”
― Jon Knokey, Theodore Roosevelt and the Making of American Leadership
― “‘They [Rough Riders] would be willing to go into the jaws of death to serve him,’ Sergeant Ledwidge stated frankly, ‘because he would do the same for them.’”
― Jon Knokey, Theodore Roosevelt and the Making of American Leadership
Given the book’s subtitle, Knokey includes little discussion or analysis linking Teddy Roosevelt to the “Making of American Leadership.” The connection is largely implicit. The most interesting part of the book, by far, is the recounting of the formation of the Rough Riders and the battle of San Juan Hill. I would give the first half of the book three stars; the book is saved only by the second half. The author either chose or was forced to go with an independent publisher, Skyhorse Publishing, which did a poor job of editing. The book has numerous misspelled words and the occasional omitted word. Four stars is probably being a bit generous.
― Jon Knokey, Theodore Roosevelt and the Making of American Leadership
Theordore Roosevelt remains one of America’s most remarkable presidents, and with good reason. His personality and achievements make him unforgettable. He is often considered the first modern President because he significantly expanded the influence and power of the executive office. Surveys of historians and political scientists over the past decade have rated him the fourth best president, behind only George Washington, Franklin Delano Roosevelt, and Abraham Lincoln. The story of how Theodore Roosevelt became President is worthy of our attention. Perhaps that is why this makes the eighth book I have read about the 26th President of the United States, including Edmund Morris’s excellent three-volume biography.
In his first book, Theodore Roosevelt and the Making of American Leadership, author Jon Knokey has chosen to focus on the development of Roosevelt’s leadership skills. To understand the leadership of Theodore Roosevelt, one must understand a little of his dynamic and fascinating story of his life. Teddy Roosevelt was certainly no leader as a child or during his college years at Harvard. Theodore was born into one of the wealthiest families in New York. His father was a descendant of Dutch merchants who made their fortunes in one of the most prosperous ports in America. His mother was descended from the southern aristocracy. As the son of a wealthy family, Theodore could have led a life of privilege and leisure. But, as a child, Teddy was undersized and sickly. He struggled with severe asthma and poor eyesight. Roosevelt spent most of his early childhood indoors while his siblings played outside. During this time, he developed a love of reading books from his father's library. Seeing that his son had a mind, his father told him he must make his body. To improve his health, he boxed and lifted dumbbells in a room his father had converted into a gymnasium. TR would go on to be an exponent of “the strenuous life.”
― “His father’s challenge was integral to the origin of Theodore Roosevelt’s remarkable courage and fighting spirit.”
― Jon Knokey, Theodore Roosevelt and the Making of American Leadership
When his wife and mother died on the same day, Valentine’s Day 1884, Roosevelt penned, “The light has gone out of my life.” He left his daughter in the care of his sister and went to North Dakota, where he spent two years ranching and dealing with his grief. Yet it was in this cauldron of grief and strenuous living where Theodore Roosevelt first demonstrated leadership skills.
― “Roosevelt’s time in the Badlands was also, unquestionably, the most influential period in his leadership development. … The experience took the elitist out of him.”
― Jon Knokey, Theodore Roosevelt and the Making of American Leadership
Roosevelt began his life in politics as an elected member of the New York State House, then served as the New York City Police Commissioner. He then went on to do serve as the Assistant Secretary of the Navy. When the Spanish-American War broke out, he was commissioned as a Colonel in the Army. Leading a group of volunteer soldiers known as the Rough Riders to a significant victory at the battle of San Juan Hill, Theodore Roosevelt became a national hero.
Most of the second half of the book is devoted to the story of Theodore Roosevelt and the Rough Riders. When the “Rough Riders” first met Roosevelt, they weren’t particularly impressed with this bespectacled man from the East. In time, he earned their respect, love and devotion.
― “Galloping back and forth, Roosevelt began to shout, ‘Men, we must advance! Rough Riders Forward, Come On!’ The distinction between ‘Come on!’ and ‘Go on!’ was not lost on the men.’”
― Jon Knokey, Theodore Roosevelt and the Making of American Leadership
― “‘They [Rough Riders] would be willing to go into the jaws of death to serve him,’ Sergeant Ledwidge stated frankly, ‘because he would do the same for them.’”
― Jon Knokey, Theodore Roosevelt and the Making of American Leadership
Given the book’s subtitle, Knokey includes little discussion or analysis linking Teddy Roosevelt to the “Making of American Leadership.” The connection is largely implicit. The most interesting part of the book, by far, is the recounting of the formation of the Rough Riders and the battle of San Juan Hill. I would give the first half of the book three stars; the book is saved only by the second half. The author either chose or was forced to go with an independent publisher, Skyhorse Publishing, which did a poor job of editing. The book has numerous misspelled words and the occasional omitted word. Four stars is probably being a bit generous.
May 9, 2022
Here's a simple case for reading this book no matter who you are.[1] If you haven’t read much about TR before, this is a fine introduction. It covers all the essential highlights of his young life, running from birth through his infamous inauguration to the Presidential office. If you have read about TR, even extensively, there is plenty of new material which makes for a refreshing trek on a familiar trail. That’s really the book’s raison d’etre. As a graduate student at Harvard, Knokey unearthed a trove of unpublished first-hand letters and research notes from TR’s contemporaries. These correspondences bring out new aspects of old anecdotes, a turning of a diamond in the hand that offers a different perspective.
Structurally, the book is divided into three sections.
The first covers TR’s youth. Knokey’s analysis here is incisive and arresting. The second section picks up just after his Harvard years, following him to the Badlands and back where he emerged a remade man. These two sections are each roughly 100 pages. The third section makes up the last 200 pages on its own, and while it briefly hits each stop in TR’s early career, its focus narrows on his time leading the Rough Riders into battle in Cuba. This is the book's heart, in substance and in spirit.
Knokey’s writing is engaging, and at times, it soars.[2] There’s an extra element of enjoyment that I have in those moments since Knokey isn’t a professional author. Books written purely as passion projects have an additional texture to them, a personal dimension that cannot be replicated by serial authors no matter how respected they be.
There are a number of misprints and mistakes, however, many of which occur in the late chapters, just when the story is reaching its crescendo. There’s the “Mason-Dixie line” on page 208 and the “Spainish government” on page 230. There are misspellings of other sorts: conquor (p. 282) and sene (not scene, p. 354). There are also weird mixed-tense sentences. “A courier from headquarters rode up to Theodore and tells him that the Rough Riders were to proceed into the valley…” (p. 344)[3] This past-present soup repeats many times over, to the point of being a distraction (to me anyway).
I can hear the objection. You’re gonna drag the book over some typos?
I call as my witness C.S. Lewis: “A good shoe is a shoe you don’t notice. Good reading becomes possible when you need not consciously think about eyes, or light, or print, or spelling.”
A good book—a really good book—draws you into its atmosphere. The story encompasses you unawares. It’s only later, after setting the book down, that you’ve realized what happened—that you were transported to a different world. Editorial oversights like these burst that bubble. The magic is lost. Instead of subconsciously breathing the air of the author’s authority, you’re waiting for the next gaffe, turning each page as if you were cautiously reaching toward a doorknob expecting a static shock. It’s an effect that undermines otherwise stellar work.
Nonetheless, my quibbles aired, I commend the book. Knokey has achieved quite the feat: He has added something of enduring value to an already saturated subject.
___
[1] I’m of course taking a shortcut here and presuming a pre-existing interest in reading about TR.
[2] For example: “As the sun peeked over the Havana Harbor skyline on February 16th, the light of dawn exposed the awesome horror of the scene. The Maine was a grotesque pile of steel and shrapnel. A lone portion of the superstructure protruded above the surface, the hull almost completely submerged. A pillar of smoke lingered indifferently above the wreckage. As dawn broke in Washington, Roosevelt, an early riser, woke quietly so as not to disturb his dangerously ill wife. He ate a breakfast of hard-boiled eggs, before arriving at his office where he was briefed on the news reports. 'I would give anything if President McKinley would order the fleet to Havana tomorrow,' he immediately stated, 'The Maine was sunk by an act of dirty treachery on the part of the Spaniards.'” // That’s inspired writing!
[3] I don’t know, maybe grammatically that’s correct? But it reads awkward to me. What if it were, “A courier from headquarters rode up to Theodore and told him that the Rough Riders were to proceed into the valley…” or, “A courier from headquarters rides up to Theodore and tells him that the Rough Riders are to proceed into the valley…” Wouldn't either of those be more natural?
Structurally, the book is divided into three sections.
The first covers TR’s youth. Knokey’s analysis here is incisive and arresting. The second section picks up just after his Harvard years, following him to the Badlands and back where he emerged a remade man. These two sections are each roughly 100 pages. The third section makes up the last 200 pages on its own, and while it briefly hits each stop in TR’s early career, its focus narrows on his time leading the Rough Riders into battle in Cuba. This is the book's heart, in substance and in spirit.
Knokey’s writing is engaging, and at times, it soars.[2] There’s an extra element of enjoyment that I have in those moments since Knokey isn’t a professional author. Books written purely as passion projects have an additional texture to them, a personal dimension that cannot be replicated by serial authors no matter how respected they be.
There are a number of misprints and mistakes, however, many of which occur in the late chapters, just when the story is reaching its crescendo. There’s the “Mason-Dixie line” on page 208 and the “Spainish government” on page 230. There are misspellings of other sorts: conquor (p. 282) and sene (not scene, p. 354). There are also weird mixed-tense sentences. “A courier from headquarters rode up to Theodore and tells him that the Rough Riders were to proceed into the valley…” (p. 344)[3] This past-present soup repeats many times over, to the point of being a distraction (to me anyway).
I can hear the objection. You’re gonna drag the book over some typos?
I call as my witness C.S. Lewis: “A good shoe is a shoe you don’t notice. Good reading becomes possible when you need not consciously think about eyes, or light, or print, or spelling.”
A good book—a really good book—draws you into its atmosphere. The story encompasses you unawares. It’s only later, after setting the book down, that you’ve realized what happened—that you were transported to a different world. Editorial oversights like these burst that bubble. The magic is lost. Instead of subconsciously breathing the air of the author’s authority, you’re waiting for the next gaffe, turning each page as if you were cautiously reaching toward a doorknob expecting a static shock. It’s an effect that undermines otherwise stellar work.
Nonetheless, my quibbles aired, I commend the book. Knokey has achieved quite the feat: He has added something of enduring value to an already saturated subject.
___
[1] I’m of course taking a shortcut here and presuming a pre-existing interest in reading about TR.
[2] For example: “As the sun peeked over the Havana Harbor skyline on February 16th, the light of dawn exposed the awesome horror of the scene. The Maine was a grotesque pile of steel and shrapnel. A lone portion of the superstructure protruded above the surface, the hull almost completely submerged. A pillar of smoke lingered indifferently above the wreckage. As dawn broke in Washington, Roosevelt, an early riser, woke quietly so as not to disturb his dangerously ill wife. He ate a breakfast of hard-boiled eggs, before arriving at his office where he was briefed on the news reports. 'I would give anything if President McKinley would order the fleet to Havana tomorrow,' he immediately stated, 'The Maine was sunk by an act of dirty treachery on the part of the Spaniards.'” // That’s inspired writing!
[3] I don’t know, maybe grammatically that’s correct? But it reads awkward to me. What if it were, “A courier from headquarters rode up to Theodore and told him that the Rough Riders were to proceed into the valley…” or, “A courier from headquarters rides up to Theodore and tells him that the Rough Riders are to proceed into the valley…” Wouldn't either of those be more natural?
October 16, 2020
A true American legend
I cannot think of a better book for every leader to read to help people overcome difficulties. TR was born into privilege as a scrawny boy that struggled with asthma. He was not satisfied with who he was and determined to transform himself into a man who could be respected. In politics, on the frontier, and in battle, he rose to every occasion. Every lover of history will be unable to put this book down.
I cannot think of a better book for every leader to read to help people overcome difficulties. TR was born into privilege as a scrawny boy that struggled with asthma. He was not satisfied with who he was and determined to transform himself into a man who could be respected. In politics, on the frontier, and in battle, he rose to every occasion. Every lover of history will be unable to put this book down.
November 4, 2025
Teddy Roosevelt is one of those characters from US history that I've heard about all my life but had never dug deeply into knowing about in detail. This book has corrected that deficiency. I highly recommend this glimpse into one of the late 19th century's and early 20th century's great leaders.
I was struck by T. Roosevelt's audacity. His straightforward, bull-in-a-china-shop approach to leadership. I had to draw comparisons to the 45th/47th president, and I finally came to the conclusion that the primary difference seems to lie in TR's concern for what was right, true, and noble. His willingness to be self-sacrificial even though he might bully his way through red-tape. He didn't divide to lead. Rather, he united diverse individuals to lead whatever organization he took hold of, whether it was on a cattle drive in North Dakota, a police force in New York, a group of ragtag soldiers in Cuba, or the United States of America. And, another rare feature these days, he led from the front.
This is a great study in leadership, what works, what doesn't work, and the difference that determined, principled perseverance can make in the lives of citizens of a nation.
I was struck by T. Roosevelt's audacity. His straightforward, bull-in-a-china-shop approach to leadership. I had to draw comparisons to the 45th/47th president, and I finally came to the conclusion that the primary difference seems to lie in TR's concern for what was right, true, and noble. His willingness to be self-sacrificial even though he might bully his way through red-tape. He didn't divide to lead. Rather, he united diverse individuals to lead whatever organization he took hold of, whether it was on a cattle drive in North Dakota, a police force in New York, a group of ragtag soldiers in Cuba, or the United States of America. And, another rare feature these days, he led from the front.
This is a great study in leadership, what works, what doesn't work, and the difference that determined, principled perseverance can make in the lives of citizens of a nation.
August 16, 2022
General Overview
A delve into the life of one of the most famous American Presidents, before he took up the Oval Office, this book is a great mix of biography, and treatises on leadership. Well researched, and very readable.
Style
Mr Jon Knokey knows his subject very well. This is clear from how insightful a work this is, whilst being a pleasure to read. Such combinations of narrative biography with essay to leadership could feel stilted or clunky. It is not this, and moves easily and naturally between the two throughout. This may be because the lessons on leadership are not stated clearly, or listed in any section. They do however shine out from each page. I imagine the subject matter of this piece enables this more then anything else.
Substance
Theodore Roosevelt is an astounding figure in history. This book only helps cement this view more firmly for me. I had no idea of the struggles he had growing up, and what sort of young man he was. Of course, his personal and physical struggles were made more easy from the family he was born into. But then, from this place of privilege, its amazing how much he strove for the common man, and to live with them.
This books covers the life of Theodore from his youth up to his rise to the precedency. Great focus placed on his time as a Lt Col with his own named Rough Riders in the Spanish American War, along with his times learning the ways of Cowfolk in the then Badlands. It makes sense for these to be the focus of this book. It wants to cover leadership, and its in these two phases of his life that Theodore shows some of the best lessons for any leader to listen to.
Final Thoughts
A great read. One I will recommend to anyone in a position of leadership, management, or as a teacher. It is also a wonderful introduction to the life of Mr Theodore Roosevelt.
A delve into the life of one of the most famous American Presidents, before he took up the Oval Office, this book is a great mix of biography, and treatises on leadership. Well researched, and very readable.
Style
Mr Jon Knokey knows his subject very well. This is clear from how insightful a work this is, whilst being a pleasure to read. Such combinations of narrative biography with essay to leadership could feel stilted or clunky. It is not this, and moves easily and naturally between the two throughout. This may be because the lessons on leadership are not stated clearly, or listed in any section. They do however shine out from each page. I imagine the subject matter of this piece enables this more then anything else.
Substance
Theodore Roosevelt is an astounding figure in history. This book only helps cement this view more firmly for me. I had no idea of the struggles he had growing up, and what sort of young man he was. Of course, his personal and physical struggles were made more easy from the family he was born into. But then, from this place of privilege, its amazing how much he strove for the common man, and to live with them.
This books covers the life of Theodore from his youth up to his rise to the precedency. Great focus placed on his time as a Lt Col with his own named Rough Riders in the Spanish American War, along with his times learning the ways of Cowfolk in the then Badlands. It makes sense for these to be the focus of this book. It wants to cover leadership, and its in these two phases of his life that Theodore shows some of the best lessons for any leader to listen to.
Final Thoughts
A great read. One I will recommend to anyone in a position of leadership, management, or as a teacher. It is also a wonderful introduction to the life of Mr Theodore Roosevelt.
September 28, 2019
A masterful book about the building blocks that made Teddy Roosevelt into the leader he was, Jon Knokey's biography tells a rich and compelling story by focusing on his upbringing and rise to power.
Roosevelt had a genius for empathy, with a specialty for drawing together people from disparate backgrounds and points of view toward common ground. A great uniter, Roosevelt's leadership helped heal a divided nation that still bristled with resentment and mistrust in the decades after the Civil War.
Of his countless endearing qualities, Roosevelt's most appealing and convincing trait was the willingness to get his own hands dirty, sacrificing his comfort to prove his work ethic and commitment to others.
With a pirate's mentality, Roosevelt spurned the establishment and disrupted embedded processes. In accomplishing his goals, he established an end vision, then worked ferociously to destroy anything that stood between him and his desire.
In taking on the Audible edition, narrator Brian Holsopple adds a vigor and passion to Roosevelt's words and deeds that captured the essence of Teddy himself.
Bulging with exhaustive research melded with an easygoing storyteller's momentum, Knokey's writing is an exquisite match for Roosevelt's bravado and manner. His respect and admiration of Roosevelt's philosophy and life force seep through in his writing, but there's also enough distance for occasional astute criticism.
Teddy Roosevelt is clearly Knokey's favorite president, and it's nearly impossible to get through is book without Roosevelt becoming your favorite as well.
Roosevelt had a genius for empathy, with a specialty for drawing together people from disparate backgrounds and points of view toward common ground. A great uniter, Roosevelt's leadership helped heal a divided nation that still bristled with resentment and mistrust in the decades after the Civil War.
Of his countless endearing qualities, Roosevelt's most appealing and convincing trait was the willingness to get his own hands dirty, sacrificing his comfort to prove his work ethic and commitment to others.
With a pirate's mentality, Roosevelt spurned the establishment and disrupted embedded processes. In accomplishing his goals, he established an end vision, then worked ferociously to destroy anything that stood between him and his desire.
In taking on the Audible edition, narrator Brian Holsopple adds a vigor and passion to Roosevelt's words and deeds that captured the essence of Teddy himself.
Bulging with exhaustive research melded with an easygoing storyteller's momentum, Knokey's writing is an exquisite match for Roosevelt's bravado and manner. His respect and admiration of Roosevelt's philosophy and life force seep through in his writing, but there's also enough distance for occasional astute criticism.
Teddy Roosevelt is clearly Knokey's favorite president, and it's nearly impossible to get through is book without Roosevelt becoming your favorite as well.
April 3, 2026
Bull Moose in the China Shop.
Jon Knokey’s *Theodore Roosevelt and the Making of American Leadership* (2015) is a solid introductory biography of the colorful Bull Moose that focuses squarely on how one of America’s most dynamic presidents forged his distinctive leadership style.
Knokey traces TR from his privileged New York upbringing through Harvard and into the rough-and-tumble world of politics, but the book is most rewarding and truest to its premise when it pulls Roosevelt out of his wealthy society circles and drops him into the Dakota Badlands or places him at the head of the Rough Riders in Cuba. Those two sections receive the most page time, and deservedly so. It is here that the reader watches Roosevelt develop his unmistakably populist and authentic voice: one that looked past class and breeding and judged men solely on character and strength of virtue. In the Badlands and on San Juan Hill, TR learns how to motivate, inspire, and ultimately lead like-minded men through sheer force of will and personal example.
As a straightforward survey biography, the book takes a bit too long to reach those pivotal “in the arena” moments, which makes it harder to fully gauge exactly how much leadership Teddy was developing in his earlier years. Still, once Knokey places his subject in those crucible experiences, the book’s value becomes obvious. The narrative snaps into focus, the anecdotes come alive, and Roosevelt’s larger-than-life personality leaps off the page.
It’s not the deepest or most scholarly treatment of TR, but as an accessible and engaging look at the making of a legendary American leader, it delivers.
Jon Knokey’s *Theodore Roosevelt and the Making of American Leadership* (2015) is a solid introductory biography of the colorful Bull Moose that focuses squarely on how one of America’s most dynamic presidents forged his distinctive leadership style.
Knokey traces TR from his privileged New York upbringing through Harvard and into the rough-and-tumble world of politics, but the book is most rewarding and truest to its premise when it pulls Roosevelt out of his wealthy society circles and drops him into the Dakota Badlands or places him at the head of the Rough Riders in Cuba. Those two sections receive the most page time, and deservedly so. It is here that the reader watches Roosevelt develop his unmistakably populist and authentic voice: one that looked past class and breeding and judged men solely on character and strength of virtue. In the Badlands and on San Juan Hill, TR learns how to motivate, inspire, and ultimately lead like-minded men through sheer force of will and personal example.
As a straightforward survey biography, the book takes a bit too long to reach those pivotal “in the arena” moments, which makes it harder to fully gauge exactly how much leadership Teddy was developing in his earlier years. Still, once Knokey places his subject in those crucible experiences, the book’s value becomes obvious. The narrative snaps into focus, the anecdotes come alive, and Roosevelt’s larger-than-life personality leaps off the page.
It’s not the deepest or most scholarly treatment of TR, but as an accessible and engaging look at the making of a legendary American leader, it delivers.
July 18, 2025
Jon Knokey is an American historian, politician, and business leader. He has served as a legislator in Montana. Theodore Roosevelt and the Making of American Leadership is a historical biography, with a sharp lens on leadership development. Its primary appeal is to readers of biography, American history enthusiasts, and anyone interested in personal growth through adversity.
This book chronicles the remarkable journey of Theodore Roosevelt from a sickly and overlooked child to the President who reshaped America’s destiny. Knokey navigates Roosevelt’s early family influences, his transformative years at Harvard, through ranch life, war service, and his meteoric rise in politics. Drawing upon newly uncovered letters and first-hand accounts, the narrative explores Roosevelt’s setbacks, moments of self-doubt, and the hard-fought lessons that fuelled his determined, sometimes contradictory, brand of leadership. It’s not just a tale of triumph but of self-forging amid failure—a study in how ambition and adaptability can unite a deeply divided nation. This book focuses more on Roosevelt's leadership and it tends to avoid deeper analysis of his flaws or the lasting impact of some controversial decisions.
Memorable Quote
“If I have anything at all resembling genius, it is in the gift for leadership . . . To tell the truth, I like to believe that, by what I have accomplished without great gifts, I may be a source of encouragement to Americans.”
This book chronicles the remarkable journey of Theodore Roosevelt from a sickly and overlooked child to the President who reshaped America’s destiny. Knokey navigates Roosevelt’s early family influences, his transformative years at Harvard, through ranch life, war service, and his meteoric rise in politics. Drawing upon newly uncovered letters and first-hand accounts, the narrative explores Roosevelt’s setbacks, moments of self-doubt, and the hard-fought lessons that fuelled his determined, sometimes contradictory, brand of leadership. It’s not just a tale of triumph but of self-forging amid failure—a study in how ambition and adaptability can unite a deeply divided nation. This book focuses more on Roosevelt's leadership and it tends to avoid deeper analysis of his flaws or the lasting impact of some controversial decisions.
Memorable Quote
“If I have anything at all resembling genius, it is in the gift for leadership . . . To tell the truth, I like to believe that, by what I have accomplished without great gifts, I may be a source of encouragement to Americans.”
August 2, 2025
This is a greatly insightful view of Teddy. It balances the line between purely biographical and persuasive. It does focus remarkably on the leadership of Teddy, not just on Teddy, hence the title. It surprised me that so much of the book is dedicated to the Spanish-American war and not more on his presidency.
I found it hard to keep up with at times. Not for a lack of interest, which did eventually start waning after listening to essentially the entire history of the Spanish-American war. The author would follow a line to a certain point and then jump back 30 years to discuss something else. It happened quite often in the beginning of the book when discussing Teddy’s ancestors.
Overall, I would absolutely recommend this book to others, especially those who care about the future of America. I had no idea how strongly Theodore bucked the norm of the day and fought for reform. I found it very beneficial and inspirational to read about his escapades and I hope you do as well!
I found it hard to keep up with at times. Not for a lack of interest, which did eventually start waning after listening to essentially the entire history of the Spanish-American war. The author would follow a line to a certain point and then jump back 30 years to discuss something else. It happened quite often in the beginning of the book when discussing Teddy’s ancestors.
Overall, I would absolutely recommend this book to others, especially those who care about the future of America. I had no idea how strongly Theodore bucked the norm of the day and fought for reform. I found it very beneficial and inspirational to read about his escapades and I hope you do as well!
February 15, 2021
This is an insightful looking into how Theodore Roosevelt became a leader. The author details that as a child and a college student Teddy did not assume leadership roles or showed any leadership promise. It's only after college that Roosevelt developed into one of the most admired leaders and presidents in America. Not only does this book give insight into what drove Roosevelt, but it shows how great leaders are created, not born. This book focuses on Roosevelt before his Presidency and only briefly covers his term as president and afterward. Relative to the many other works on Roosevelt's life, this book is a reasonable length for the time covered. Thus, it is an approachable place to start for those interested in learning more about Roosevelt but intimidated by some of the much longer works out there.
June 19, 2023
This was a decent look at how Roosevelt developed and became a leader of his own making. The archival material was used well to provide scene setting detail and interesting insights.
I think where the book was weaker was its lack of a properly critical look at the man beyond his childhood. At times it seemed the author wanted to canonise him. I think the model for how to write a biography on a man larger than life with some critical thought applied would be Black Spartacus: The Epic Life of Toussaint Louverture by Sudhir Hazareesingh.
There also wasn’t much detail given on his presidency - surely the greatest challenge in providing leadership?
This is a ‘low’ four stars from me, with some of the flaws in the book made up for somewhat by the incredible detail and tying together of archival documents into an accessible historical narrative.
I think where the book was weaker was its lack of a properly critical look at the man beyond his childhood. At times it seemed the author wanted to canonise him. I think the model for how to write a biography on a man larger than life with some critical thought applied would be Black Spartacus: The Epic Life of Toussaint Louverture by Sudhir Hazareesingh.
There also wasn’t much detail given on his presidency - surely the greatest challenge in providing leadership?
This is a ‘low’ four stars from me, with some of the flaws in the book made up for somewhat by the incredible detail and tying together of archival documents into an accessible historical narrative.
November 5, 2025
I listened to this non fiction book on Theodore Roosevelt as an audiobook. It is included in your membership if you have Audible.
This was a really well written, easy to follow book on the pre-presidential life of Theodore Roosevelt, showing how this well known and often quoted American president was not a born leader. The book follows his journey from being a sickly child, to losing his first wife and finding some solace in the wilderness, to leading the Rough Riders to Cuba, just to mention a few stages in his life and how all these experiences made him the kind of person who could unite a nation and be liked and respected by people of different backgrounds.
I always enjoy historical books which look at people or events from more of an unusual perspective and I felt this is such a book. Good narration too.
This was a really well written, easy to follow book on the pre-presidential life of Theodore Roosevelt, showing how this well known and often quoted American president was not a born leader. The book follows his journey from being a sickly child, to losing his first wife and finding some solace in the wilderness, to leading the Rough Riders to Cuba, just to mention a few stages in his life and how all these experiences made him the kind of person who could unite a nation and be liked and respected by people of different backgrounds.
I always enjoy historical books which look at people or events from more of an unusual perspective and I felt this is such a book. Good narration too.
February 28, 2025
TR did most of the work for his biographers by being a fascinating man who lived an adventurous life. He's right up there with Abraham Lincoln as one of the most likable presidents in American history as well. The first grown up presidential biography I ever read was The Rise of Theodor Roosevelt, by Edmund Morris, which, like this book, covered his early life. I have considered TR a hero ever since I read Morris's book. I’ve been thinking about rereading it for a while, but this book filled that space for me (for now anyway). Very readable and insightful about how Roosevelt developed as a man and a leader. If you want TR’s whole life, look elsewhere, but this book brings you from infancy through the Rough Riders with nary a dull moment.
October 26, 2020
Lots of books are written about historical figures and leaders, including many about the subject of this book. I am a strong proponent for reading biographies for the insights we can draw from them, and I am a big fan of American History in general, so you might think I would be drawn to this book for those reasons, and you would be correct.
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February 17, 2022
I knew he was a great man and that's why I got and read the book. I learned that he was both greater and more flawed than I knew. also learned some interesting history that I didn't know before. well worth the read.
September 23, 2025
The Real Teddy Roosevelt
Very thorough account of Teddy Roosevelt. Much of the information is not sugar coated. Makes you question why we can't find an individual who shares the same qualities that Teddy Roosevelt did. Doubtful we ever will again.
Very thorough account of Teddy Roosevelt. Much of the information is not sugar coated. Makes you question why we can't find an individual who shares the same qualities that Teddy Roosevelt did. Doubtful we ever will again.
August 12, 2019
Thorough investigation!
Read
November 23, 2020Audible Audiobook
April 30, 2023
A little boring. All about the part of his life before his presidency. Interesting but not that much.
September 30, 2025
Fascinating read about a fascinating man. Recommended to anyone interested in American history.
March 3, 2026
All my Teddy lovers to the front! Great accounts of the Spanish American War. Also focused on his many government jobs before the presidency and how that shaped his leadership. This is not about his presidency at all, more about the lead up.
May 28, 2016
Summary:
In the preface, the casket of Abraham Lincoln is in route through New York City. It will journey through several states on its way to Illinois for burial. People gather beside the roads to pay their respects to the fallen 16th president. Young Theodore Roosevelt, and his brother, Elliott, are spectators of the funeral procession. Their view is from a second floor window. They are viewing a critical moment in American history. Later, Theodore will spark his own pivotal moments in history. Theodore was an unlikely leader, he had health problems as a youth, and he was known as an arrogant fellow in college. Further, he came from a wealthy background affording him to live in luxury and to associate with the upper class of people. However, several responsibilities and life experiences molded him into a man who became a capable leader,
But it was not the charge up the hill that put him in the White House. It was his ability to lead those from different backgrounds that made him president of the United States. He knew how to lead the Fifth Avenue clubman of New York as well as the frontiersman from the West. And when he got the opportunity to lead them together, he healed the scars of the Civil War and united a nation around a new vision: America as a superpower. Page xiii
The book is divided into three parts: "foundation," "ruling," and "leading."
The book stops at the point where Theodore Roosevelt takes the oath of office as the 26th president of the United States.
Highlights of the book is Theodore's childhood and youth, personal life, Civil Service Commission, term as New York City Police Commissioner, the training of the Rough Riders, and the Spanish-American War.
A strong endnotes and bibliography is included.
My Thoughts:
When I read a biography, I am hoping the character will come alive as a flesh and blood person. I've read biographies before where the characters are academic and cold. In Theodore Roosevelt and The Making of American Leadership, Theodore Roosevelt lives and breathes.
Additional reasons for giving this book 5 stars for excellent:
Theodore Roosevelt is dimensional. I learned of his strengths and weaknesses. He was a complicated man to pin down as one distinct personality. After reading the book, I see him as a dynamic man with moments of passion and activity. He is a man of vision and idea. He is a man who has the strong ability to befriend a person of any rank, culture, race, or socioeconomic class. However, he is a man who can be stoic, withdrawing during periods of depression.
Theodore Roosevelt is a hero for all people who have wrestled with a disability. He had a childhood illness, was weak in physicality, and possibly had a depressive health condition.
He was a voracious reader. He is a man after mine own heart.
He was unafraid to get dirty. He worked alongside his soldiers. He ate when they ate. Slept where they slept.
Life experiences transformed him, they "made" him. He did not give up, but persevered through hardships to the next step and then the next step. He was bully!
If I could visually see Theodore. I am sure my eyes would not want to turn-away. Knokey has captured this essence of Theodore by keeping my attention from the first page to the last page.
He was a person who wanted to "know" people. He was unafraid and unhindered to grasp the hand of a working class man. He did not place himself on a level above or below.
One of the aims of the book, and it is reflected in the title, is "The Making of American Leadership." I believe this book should be required reading for those who are at this moment in American history wanting to become the next president. Isn't this the kind of president we want? A person who hears what the American people are saying (both listening with the ears, and hearing with the mind and heart), and will execute just action (not sweep away those things that are not beneficial politically.)
Source: Free copy from Jon Knokey and Author Marketing Experts in exchange for a review.
Rating: 5 stars for excellent
In the preface, the casket of Abraham Lincoln is in route through New York City. It will journey through several states on its way to Illinois for burial. People gather beside the roads to pay their respects to the fallen 16th president. Young Theodore Roosevelt, and his brother, Elliott, are spectators of the funeral procession. Their view is from a second floor window. They are viewing a critical moment in American history. Later, Theodore will spark his own pivotal moments in history. Theodore was an unlikely leader, he had health problems as a youth, and he was known as an arrogant fellow in college. Further, he came from a wealthy background affording him to live in luxury and to associate with the upper class of people. However, several responsibilities and life experiences molded him into a man who became a capable leader,
But it was not the charge up the hill that put him in the White House. It was his ability to lead those from different backgrounds that made him president of the United States. He knew how to lead the Fifth Avenue clubman of New York as well as the frontiersman from the West. And when he got the opportunity to lead them together, he healed the scars of the Civil War and united a nation around a new vision: America as a superpower. Page xiii
The book is divided into three parts: "foundation," "ruling," and "leading."
The book stops at the point where Theodore Roosevelt takes the oath of office as the 26th president of the United States.
Highlights of the book is Theodore's childhood and youth, personal life, Civil Service Commission, term as New York City Police Commissioner, the training of the Rough Riders, and the Spanish-American War.
A strong endnotes and bibliography is included.
My Thoughts:
When I read a biography, I am hoping the character will come alive as a flesh and blood person. I've read biographies before where the characters are academic and cold. In Theodore Roosevelt and The Making of American Leadership, Theodore Roosevelt lives and breathes.
Additional reasons for giving this book 5 stars for excellent:
Theodore Roosevelt is dimensional. I learned of his strengths and weaknesses. He was a complicated man to pin down as one distinct personality. After reading the book, I see him as a dynamic man with moments of passion and activity. He is a man of vision and idea. He is a man who has the strong ability to befriend a person of any rank, culture, race, or socioeconomic class. However, he is a man who can be stoic, withdrawing during periods of depression.
Theodore Roosevelt is a hero for all people who have wrestled with a disability. He had a childhood illness, was weak in physicality, and possibly had a depressive health condition.
He was a voracious reader. He is a man after mine own heart.
He was unafraid to get dirty. He worked alongside his soldiers. He ate when they ate. Slept where they slept.
Life experiences transformed him, they "made" him. He did not give up, but persevered through hardships to the next step and then the next step. He was bully!
If I could visually see Theodore. I am sure my eyes would not want to turn-away. Knokey has captured this essence of Theodore by keeping my attention from the first page to the last page.
He was a person who wanted to "know" people. He was unafraid and unhindered to grasp the hand of a working class man. He did not place himself on a level above or below.
One of the aims of the book, and it is reflected in the title, is "The Making of American Leadership." I believe this book should be required reading for those who are at this moment in American history wanting to become the next president. Isn't this the kind of president we want? A person who hears what the American people are saying (both listening with the ears, and hearing with the mind and heart), and will execute just action (not sweep away those things that are not beneficial politically.)
Source: Free copy from Jon Knokey and Author Marketing Experts in exchange for a review.
Rating: 5 stars for excellent
April 15, 2016
The personal struggles and successes of Teddy Roosevelt
As an adult, I still regarded Teddy Roosevelt's presidency with much respect. This book is great at capturing the stories that make Teddy or Thee Roosevelt so unique.
I don't remember hearing in high school history that Mr. Roosevelt battled health issues. I thought this was more noteworthy with his distant cousin, Franklin D. Roosevelt. Teddy battled terrible asthmatic attacks starting at age 3 and unknowingly had poor vision for several years until he got spectacles in his teens. He was also diagnosed with a week heart during college days. As a kid, he was picked on for being scrawny and learned how to fight back after being bullied. After the heart diagnosis, he was told to live pretty much a sedentary life. Teddy seemed to have a lot of spunk and could not accept living with as always sitting down.
He was financially secure from the start, but suffered tragic losses, like his father dying when he was only 46 and his mother at age 48 and wife at age 22 being laid to rest. His wife was a mother for only 40 hours before her passing. I think we are often taught of an important person's successes and do not often hear of the struggles and hardships that these individuals have experienced that make their achievements even more substantial in history.
I received this book in exchange of an honest and unbiased review.
As an adult, I still regarded Teddy Roosevelt's presidency with much respect. This book is great at capturing the stories that make Teddy or Thee Roosevelt so unique.
I don't remember hearing in high school history that Mr. Roosevelt battled health issues. I thought this was more noteworthy with his distant cousin, Franklin D. Roosevelt. Teddy battled terrible asthmatic attacks starting at age 3 and unknowingly had poor vision for several years until he got spectacles in his teens. He was also diagnosed with a week heart during college days. As a kid, he was picked on for being scrawny and learned how to fight back after being bullied. After the heart diagnosis, he was told to live pretty much a sedentary life. Teddy seemed to have a lot of spunk and could not accept living with as always sitting down.
He was financially secure from the start, but suffered tragic losses, like his father dying when he was only 46 and his mother at age 48 and wife at age 22 being laid to rest. His wife was a mother for only 40 hours before her passing. I think we are often taught of an important person's successes and do not often hear of the struggles and hardships that these individuals have experienced that make their achievements even more substantial in history.
I received this book in exchange of an honest and unbiased review.
April 16, 2016
Theodore Roosevelt and the Making of American Leadership is a biographical narrative that focuses on Roosevelt’s growth and maturity in regard to his ability to becoming a strong and celebrated leader. Knokey gained access to previously unpublished letters of people writing to and about Roosevelt, which help give more detail and deeper insight into Roosevelt’s actions and history.
I’ve read about the major details and historically significant moments in Roosevelt’s life, and I really liked having a more informative and personal look at the real man behind the presidential icon. Knokey does a great job of building the world around Roosevelt and his history, and also brings the man’s journey to becoming a great leader to life.
I received a free copy of the book in exchange for an honest review.
I’ve read about the major details and historically significant moments in Roosevelt’s life, and I really liked having a more informative and personal look at the real man behind the presidential icon. Knokey does a great job of building the world around Roosevelt and his history, and also brings the man’s journey to becoming a great leader to life.
I received a free copy of the book in exchange for an honest review.
July 20, 2016
American leadership could learn something here...
Absolutely loved this book. Not only does it chronicle the pre-presidential life of TR, but it does so through the lens of leadership. How this man developed as a leader is an important lesson that our current leaders in the U.S. could derive some benefits from reading and applying.
Absolutely loved this book. Not only does it chronicle the pre-presidential life of TR, but it does so through the lens of leadership. How this man developed as a leader is an important lesson that our current leaders in the U.S. could derive some benefits from reading and applying.
August 15, 2016
I'd give three stars as a starting point for any book about TR. Although I enjoyed this book, the title is a little deceptive. Rather than examining TR's relationship to leadership throughout his life, the bulk/majority of this book is dedicated to the Battle of San Juan Heights. Good, but not great.
December 1, 2015
I really enjoyed this book. The more I learn about Theodore Roosevelt, the more I like him as a person. This book did not talk about his deeds as President, yet more how he developed himself as a person to rise to the top and be a great leader in everything he did. Really great read.
January 3, 2016
This was mostly new story for me. Usually I read a lot of repeat on TR. Jon Knokey found some new or lesser known history, and I enjoyed it. Goodread for any TR fan.
April 10, 2016
This book has become my favorite on TR. well researched and well written.
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