A Reader’s Guide to the Lifework of Theodore Roosevelt

I’m only half joking when I tell people that Theodore Roosevelt’s time as President was the least interesting aspect of his life.

The reality is that T.R’s presidency was only a small portion of his life’s work—work that spanned the full spectrum of careers, from sedentary, high-brow intellectual pursuits to the action-packed violence of war, with a variety of wide-ranging jobs in between.

Because he was able to fit several lifetimes of work into his 60 years, understanding T.R.’s impact on history requires much more examination than what any single, measly biography can offer.

So, I’m offering up a few of my favorite T.R. books, each delving into a specific facet of his life and work. Whether you read one of them or all of them, I can guarantee that each of these books will give you a much deeper appreciation for the strengths, failings, and lasting influence of this complex man.

Conservationist – The Wilderness Warrior: Theodore Roosevelt and the Crusade for America by Douglas Brinkley. Many would argue that T.R.’s most enduring legacy is his work in conservation—species protection, public lands, and his absolute contempt for the robber barons’ attempts to pillage the U.S.’s natural resources. This dense, fact-filled tome catalogs all of T.R.’s conservation accomplishments, sometimes in excruciating detail. But there is no better resource out there for understanding just how much T.R. loved wild places and how damn hard he worked to conserve them.

Cattleman – Theodore Roosevelt in the Badlands: A Young Politician’s Quest for Recovery in the American West by Roger L. DiSilvestro. Much is made of T.R.’s time spent as a “cowboy,” and this book gives an in-depth portrayal of his successes and failures as a Dakota rancher. While his time as a cattleman healed and fortified T.R. both physically and emotionally, many people overlook the fact that ranching damn near ruined him financially. If you want to dive deep into understanding all sides of West’s impact on T.R.’s legacy, this is your book.

Scientist – The Naturalist: Theodore Roosevelt, A Lifetime of Exploration, and the Triumph of American Natural History by Darrin Lunde. Before politics entered his life, T.R. was fully committed to pursuing a career in science, as a naturalist. Collecting, cataloging, and preserving birds and animals was his obsession from childhood into young adulthood, and he gained some renown within scientific circles for his contributions. This enlightening book not only details T.R.’s success and talents as a naturalist, but explains the rise of the field of study during the late 19th century.

Hunter – Hunting Trips of a Ranchman & The Wilderness Hunter by Theodore Roosevelt. Much has been written about T.R.’s obsession with hunting—some call him a blood-lusting maniac and others revere him as the savior of big game. To help form your opinion, I recommend going straight to the source and reading these two entertaining, educational, and revealing works by the man himself.

Crime Fighter – Island of Vice: Theodore Roosevelt’s Doomed Quest to Clean Up Sin-Loving New York by Richard Zacks. If any phase of T.R.’s life could be categorized as a failure, it would be his stint as a New York City police commissioner. His unyielding standards and bombastic personality, combined with his high-falutin’ self-righteousness, created a no-win situation for him in morally loose NYC. I’m personally very interested in the failures of successful people, and this is a failure story worth reading.

Soldier –  The War Lovers: Roosevelt, Lodge, Hearst and the Rush to Empire by Evan Thomas. If there is a single anecdote that I believe summarizes T.R.’s personality, it’s his role in the lead-up to the Spanish-American War. This book will give you valuable insights into the force of his personality, and the relentlessness with which he exerted his will on those within his orbit. There are also plenty of wonderful stories detailing the famed Rough Riders and the Battle of San Juan Hill.**

Explorer – The River of Doubt: Theodore Roosevelt’s Darkest Journey by Candice Millard. If I could only recommend one T.R. book to the general public, this would be it. Exciting, easy-to-read, and extremely educational, it’s the story of T.R.’s exploration of a tributary of the Amazon River—an expedition that nearly killed him. Even though this book is focused on this one specific adventure, it provides a deep and broad overview of T.R.’s personality and legitimate physical and mental toughness.

Child – Mornings on Horseback: The Story of an Extraordinary Family, a Vanished Way of Life and the Unique Child Who Became Theodore Roosevelt by David McCullough. McCullough is a damn genius, and everything he writes is fantastic. So obviously when he turns his attention to exploring T.R.’s family and childhood, you need to read it. I’ve heard many well-respected writers say that this is their favorite T.R. book.

Father – Theodore Roosevelt: Letters to His Children by Theodore Roosevelt.  On top of everything, TR was a committed father who loved his family madly. This collection of letters is equal parts hilarious and heartwarming—stories ranging from a ridiculous recounting of a badger running loose in the White House to pointed advice to his children encouraging them to work hard, be honest, and live up to high personal standards. I read this book at least once per year and have started reading portions of it to my oldest daughter, who loves it.

The Whole Enchilada – The Theodore Roosevelt Trilogy by Edmund Morris. I credit this trilogy, particularly the first volume, with drastically changing the trajectory of my life for the better. I happened to read them during a pivotal period of my life, and they redefined my understanding of the importance of approaching all tasks with full enthusiasm, working hard at “work worth doing,” embracing the strenuous life, and much, much more. Committing to read the full 2,400+ total pages is not for the faint of heart, but, trust me, it’s well worth the effort.

Don’t like to read? Well, how the hell did you make it this far? No matter, I’ve got a suggestion for you too: Ken Burns: The Roosevelts – An Intimate History. Nearly 14 hours of all things Roosevelt—Theodore, Eleanor, and Franklin. My suggested viewing strategy is to alternate one episode of The Roosevelts with a full showing of Road House, then repeat for 28 hours straight.

**Since writing this post, I read The Crowded Hour: Theodore Roosevelt, the Rough Riders, and the Dawn of the American Century by Clay Risen. Holy cow it was good! A completely different book than The War Lovers, one deserving of its own category. I’m not going to rewrite the post or add categories, but I highly recommend giving The Crowded Hour a read.