A Singular Life

by Jim Kratsas

Vibrant America at the dawn of the Twentieth century was poised yet hesitant to step onto the world stage.  A man embodying the energy and promise of the New World came at this opportune time.  In eight years, he made America’s presence felt across the globe, looked out for the common man, fought injustice wherever he saw it, and took on the political bosses and industrialists. And, if his two heroes, George Washington and Abraham Lincoln, had defined the presidency, he modernized it to fit a changing world.

Theodore Roosevelt barely survived childhood.  Illness might have slowed his body but his mind raced.  He transformed his sickly frame into an athletic, rugged body.  He not only became a great president, he made himself a world authority on wildlife, wrote prodigiously, fought to expand America’s armed forces and became a rancher in the Wild West.  In his life, he fought in a war that he helped start, he stopped a war and because of war suffered a broken heart.

For all of these serious aspects of TR, there was another side to the man.  It has been said that while he and his wife, Edith, had six children, Edith had seven.  He wrestled and played with his children at their home on Long Island and the grounds of the White House.  He boxed, losing his sight in one eye to a sparring partner while president.  He rode horses, swam wherever he could, including in Washington’s Potomac River, loved rowing, wrestled, played tennis and polo, organized hikes that left his comrades breathless and even took up jiujitsu.

He traveled the world meeting the crown princes of Europe, inspected his handiwork, the Panama Canal, went on safari and led an expedition to chart an unknown river.  He was the first president to fly in a plane, to travel overseas while in office, and ride in a submarine.

When Roosevelt became president upon the death of William McKinley, he was and remains our country’s youngest chief executive.  Despite his age, few had come to the office so prepared to take on its demands.  No one save possibly Jefferson was as well read.  The energy he brought to the office ensured that McKinley would soon be forgotten and America would be dragged into the new century despite any hesitation it might have.

Friends and critics called him a cowboy, a madman, a dude, four-eyes, Rough Rider, the Gunpowder Governor, Colonel, a bully, the cyclone, Bull Moose, childish, brilliant, insane, caring and daring.  One observed, “You had to hate the Colonel a whole lot to keep from loving him.”  Historian H.W. Brands stated, “Those who hated him often did so for the same reason the many more loved him:  He called to mind America’s better days and Americans’ better selves.”

When the rigors of what he termed a strenuous life ended his stay on earth at age 60, Theodore Roosevelt’s time spanned from America’s pre-Civil War era to the nation’s assumption of the world’s greatest industrial and military power.  No one was more proud of that than the bespectacled, grinning man we now know simply as TR.



Theodore Roosevelt Jr. was born into an influential family in New York City during a fall evening in 1858.  At its head was Theodore Roosevelt Sr., whom Teddy would remember fondly as “the best man I ever knew.”  His doting mother came from a Southern family, which caused more than a few tense moments during the Civil War as mother and father sided with their regional roots.

From the outset, Teedie, as he was known by his family, was plagued by illnesses including severe asthma attacks that threatened his life.  His father often nursed him and gave him the advice that would drive the studious child the rest of his life — “You have the mind, but…. you must make your body.”  So began Teedie’s lifelong dedication to exercise — wrestling, boxing, swimming, hiking, lifting weights — to make his body strong.

Teedie loved nature.  From the moment he saw a dead seal at a marketplace, he became obsessed with collecting and studying animal specimens, especially birds that he tagged and categorized.  This passion fit well with his love of the outdoors and hunting.

The second of four siblings, Teedie was very attached to his sisters Anna (affectionately known as Bamie), Corrine and brother Elliot. He traveled with his family to England, Germany, Italy, France, the Middle East and a trip down the Nile.  At each venue, TR collected bird specimens and skins, keeping thorough notes on all as well as noting in his diary the day’s exploits. On these trips the home-schooled Teedie learned to speak several languages including German, French and some Italian

Teddy entered Harvard in 1876, where he excelled in such subjects as German, history and rhetoric.  During his sophomore year, TR experienced his first tragic loss when his father died of cancer.  The heartbroken student wrote,  “Father had always been so much with me that it seems as if part of my life had been taken away.” But with a resolve that so characterized his life, TR became the man of the house, looking after his mother’s well being as well as making decisions for his siblings.

“The light has gone out of my life”
The blow of his father’s death was softened later that year when Roosevelt fell deeply in love with Alice Lee of Boston.  Tall, pretty and intelligent, Alice captured TR’s heart so thoroughly that he decided in one month to marry her.  They were engaged on Valentine’s Day 1880, a day that would in a few years be a bitter one for TR.


After a European honeymoon, Teddy and his bride returned to New York where he studied law at Columbia.  Though happily married — “I am living in a dream of delight with my darling, my true-love” — he was unsure of a career.  Law was less interesting to him than writing.  In 1880, he published his Naval History of the War of 1812 to great reviews.  But law and writing were being eclipsed by politics, a vocation that appealed to his competitiveness and sense of civic duty.  At age 23, TR was elected to the state assembly, its youngest member.  He battled political corruption, pushed for civil service reform, became minority leader in a year, and earned the nickname of the Cyclone Assemblyman. “I rose like a rocket,” he later wrote.

All seemed well for TR.  Along with his success in the State Assembly, Alice was expecting their first child. Then in early February 1884, Teddy received word in Albany that his mother, Mittie, was ill.  On February 12, a telegram announced the birth of “my little new baby.” As he received congratulations from his friends in the assembly, a second telegram arrived — Alice, too, was ill.  Rushing home, he was met by his brother Elliot who said, “There is a curse on this house.”  Mother Mittie was feverish with typhoid; Alice was dying of kidney failure.  For the next 16 hours TR went to each patient’s bed.  Mittie died in the early morning while Alice passed away later that same day — February 14, the fourth anniversary of their engagement.

It was a tremendous blow to Teddy.  His diary entry for Valentine’s Day was a black “X” followed by “the light has gone out of my life.”  After the double funeral, he wrote, “For joy or for sorrow my life has now been lived out.”

TR threw himself into his work in the Assembly and campaigned hard for the Republican party in the 1884 presidential election.  Before the election, however, Roosevelt struck out for the Dakota Territory, to a ranch near Medora he had purchased the previous year. He had fallen in love with the West, for it was a

land that offered a strenuous life outdoors.  Here amid cattle, wildlife, and rough hewn men, he could deal with his loss.

Roosevelt left his infant daughter, Alice (named after her mother), in New York with his sister, Bamie. Too pained to mention her given name, he instead referred to her as Baby Lee. It was the beginning of a strained and somewhat distant relationship between father and daughter.

A New Life and New Challenges
If Roosevelt went West to find himself and ease the pain of widowhood, he found its romance a poor substitute for a companion.  On a return trip to New York in 1885, he caught up with childhood friend Edith Carow.  They had had a falling out upon TR’s engagement to Alice, but when they came across each other the old attraction returned and soon a courtship began. By November they were secretly engaged.


Still, politics were never far from Roosevelt. In 1886, prior to the wedding, TR was nominated as Republican candidate for mayor of New York. Knowing Edith could never move out West and that New York was home, he ran but finished third in the race.  The fire, however, was back.

Married in London, TR and Edith honeymooned in Europe before returning to New York and a new home in Long Island, Sagamore Hill.  Roosevelt renewed his writing (a biography of Thomas Hart Benton and a two volume Winning of the West) and campaigned hard in 1888 for fellow Republican Benjamin Harrison’s presidential race. Harrison won and appointed TR to the U.S. Civil Service Commission. Comprised of three members, TR soon became its spokesman and lightning rod. To take this thankless job, Roosevelt moved his family to Washington, D.C.  There he developed a new circle of friends including important men such as Thomas Reed, Henry Cabot Lodge, and John Hay.

In the 1892 presidential election, Democrat Grover Cleveland regained the presidency.  But in stead of stripping TR of his Civil Service post, Cleveland saw the political benefit in keeping the energetic Roosevelt on board, giving the impression of impartiality.

TR still longed for New York and his relationship with Edith became strained when she urged him not to run again for mayor.  He declined the offer but blamed Edith.  “I would literally have given my right arm to have made the race, win or lose.  It was the one golden chance, which never returns.”  He left for Dakota soon after the decision, leaving Edith to regret having swayed her husband’s choice.  “This is a lesson that will last my life — never give it [her opinion] for it is utterly worthless when given, worse than that in this case for it has helped spoil some years of a life which I would have given my own for.”

In 1895, TR was offered the post of President of the Police Commission of New York by the new mayor.  Not only could he return home, he relished the appointment as one where he could really make a difference.  As with the Civil Service, he took on the job with gusto, transforming a corrupt, indifferent police force into one that rewarded merit over politics.  He prowled the streets at night, making sure that these police on the beat were doing their job and enforced the Sunday liquor laws that had been ignored through graft.  He put officers on bicycles, making them more mobile to combat crime.

“It was my one chance.”
The Republican Party nominated William McKinley for the 1896 Presidential election.  As a true party man, TR took on the role of attack dog lambasting Democratic nominee William Jennings Bryan across the country.  McKinley won handily and Roosevelt hoped for a job in the new administration.  But TR was seen as a rabble rouser by many in his party, including Senator Tom Platt, the political boss for New York.  Platt saw an opportunity to dump his state’s rabble in McKinley’s lap.  The reluctant President-elect fumed, “I hope he has no preconceived plans which he would wish to drive through the moment he got in.”

TR was appointed Assistant Secretary of the Navy, a prominent yet weak position.  Undaunted, TR threw his whole being into the new job, determined to make the Navy stronger and combat ready.  He pressured his boss, John Davis Long, the Secretary of the Navy, and the President to exert the nation’s influence in both the Atlantic and Pacific Oceans.

Meanwhile tensions between the United States and Spain were running high.  Spain’s handling of rebellions in Cuba, indeed its presence so close to the U.S., strained relations with America.  But when in 1898, a Navy ship, the USS Maine, sent to Cuba to protect American lives, blew up in Havana harbor, America was outraged.  The public clamored for action as newspapers fanned the flames of war.  Caught up in the frenzy, TR sprang into action, pressing for wartime legislation, putting all ships on alert, ordering fuel and ammunition, and positioning the fleet for combat.  This flurry of activity prompted President McKinley to sarcastically ask his doctor Leonard Wood (a war hawk), “Have you and Theodore declared war yet?” Wood replied, “No, Mr. President, but we think that you should.”

Roosevelt, acting in the absence of Secretary Long, ordered Commodore George Dewey’s fleet to prepare to attack the Spanish navy at Manila in the Philippines.  Dewey was in position when Congress finally declared war and he sank the Spanish fleet.

With the war officially begun, TR resigned his office and along with Wood raised a cavalry unit to fight in Cuba.  Mixing Ivy Leaguers with cowboys, the First U.S. Volunteer Cavalry became known as the Rough Riders, led by Colonel Wood and Lieutenant Colonel Roosevelt.  TR thought this his “one chance” to bathe himself in the glory of war.  Long’s response to his brash underling was no less calculating. “He is acting like a fool,” said the Secretary.  “And, yet, how absurd all this will sound if, by some turn of fortune, he should accomplish some great thing and strike a very high mark.”  Long had no idea how prophetic those words were.

After intense training in San Antonio, Wood and TR lobbied hard to Washington for their unit to be one of the first to see action in Cuba.  They got their wish, landing on the island in June 1898, though without their horses, victims to poor logistics.  In the next few days, Roosevelt would lead his men through skirmishes, including “the great day of my life,” his charge up San Juan Hill.  With disregard for himself, Roosevelt led his men through blistering, Spanish gun fire.  True courage at the most celebrated battle of the Spanish-American War, along with some self-promotion, made TR the war’s biggest hero and a coveted political figure.

Laurels for a Hero
Roosevelt’s “crowded hour” at the battle of San Juan Hill arguably made him the most popular man in America.  His exploits were toasted by the press, his image in uniform appeared everywhere and he became a prized candidate for political office.  Back in his home state of New York, Republicans thought TR the war hero a shoe-in for governor.


Yet one Republican had to be convinced: that was the party’s boss Senator Thomas Platt, before whom every Republican politician bowed.  Platt was used to controlling his officeholders. TR, he feared, might not easily bend.  But the public loved the war hero and Platt consented but warned, “If he becomes Governor of New York, sooner or later, with his personality, he will have to be President of the United States … I am afraid to start that thing going.”  TR promised to consult with Platt, but he would “act finally as my own judgment and conscience dictated.”

The race was tough.  “I am in a hot campaign.  Just as hot as Santiago was.”  With the help of other Rough Riders at rallies, Roosevelt won by fewer than 18,000 votes out of 1.3 million cast.  True to his word, TR consulted with Platt about appointments and issues, but clashed with the Senator and Republicans’ strongest supporters — businessmen — especially over proposed business taxes. Eventually, Platt’s patience with Roosevelt was overtaxed, and he sought ways to rid himself of the new governor.

But Teddy’s popularity continued to swell until party whispering began linking his name to the Presidency.  McKinley, however, surely would be reelected in 1900.  Ignoring the whispers, TR fixed his sights on another term as governor.

Platt could think of nothing worse than four more years of TR — then he struck upon a solution.  Vice President Garret Hobart had died in 1899 leaving McKinley in need of a second.  What better way to rid New York of this upstart, thought Platt, than burying him in the vice presidency, a job John Adams described as “the most insignificant office ever the invention of man contrived.”  Most Republicans at the national convention in 1900 agreed with the choice.  One, however, was appalled.  Senator Mark Hanna of Ohio, master of McKinley’s campaign screamed, “What is the matter with all of you?  Here is this convention going headlong for Roosevelt for Vice President.  Don’t any of you realize that there’s only one life between that madman and the presidency?”  But the momentum was too much.  About his nomination Roosevelt said, “The thing could not be helped.”

Once confirmed as Vice President, Hanna sighed, “The best we can do is pray fervently for the continued health of the President.”

Facing Democrat William Jennings Bryan for a second time, McKinley campaigned from his front porch in Canton, Ohio, sending Roosevelt to bay at Bryan’s heels. TR proved more than up to the task and, in November, McKinley was easily re-elected.

The energetic TR quickly became bored as vice president.  “The Vice Presidency is an utterly anomalous office (one which I think ought to be abolished).  The man who occupies it may at any moment be everything; but meanwhile he is practically nothing.”  Within six months, Roosevelt became that “everything.”

While visiting the Pan-American Exposition in Buffalo, New York, on September 6, 1901, President McKinley was gunned down by a self-proclaimed anarchist.  Roosevelt, vacationing in Vermont, sat in “stunned amazement” when he heard the news.  When he arrived in Buffalo, the Vice President found McKinley on the mend.  “Thank Heaven, the President is now out of danger.”  TR returned to New England with “a light heart” at McKinley’s recovery. But a few days later his condition took a turn for the worse, infection had set in, and McKinley died on September 14.

The worse fears of Thomas Platt and Mark Hanna had come true.  That “cowboy,” that “madman” was now President of the United States after a brief swearing-in ceremony in Buffalo.

The Bully Pulpit
One could argue that William McKinley was assassinated twice — once by Leon Czolgosz and once by the new president.  Most Americans are unaware of McKinley’s accomplishments — an unprecedented economic boom, victory in war, and carrying the nation onto the world stage.  They are forgotten because Roosevelt, by his vision, energy and re-making of the presidency, made everyone forget. Looking back on his administration, TR stated:


“I did and caused to be done many things not previously done by the President … I did not usurp power, but I did greatly broaden the use of executive power  … I acted for the public welfare, I acted for the common well-being of all our people, whenever and in whatever manner was necessary, unless prevented by direct constitutional or legislative prohibition.”

His first message to Congress removed any doubts about how he intended to use this office. In a message written by himself, President Roosevelt first eulogized McKinley. There he burst forth from his bully pulpit a wave of presidential ambition. He railed against anarchists, pushed for greater government controls over corporations, protection for workers, regulation of railroads, inspections of banks, expansion of forest reserves, flood control and conservation over natural resources.  In foreign affairs, he wanted to

strengthen the Monroe Doctrine, acquire Hawaii, Puerto Rico, and the Philippines, and strengthen the navy by increasing the size of the fleet and building a canal across Central America.

Within his first year, TR mounted attacks on those business corporations, or trusts, which were in violation of the until then little-used Sherman Anti-Trust law, which forbade anyone to restrain commerce.  He went after railroads, the oil industry and other combinations that he saw were “hurtful to the general welfare.”  He clashed with business tycoons such as J.P. Morgan and intervened in the Coal Strike of 1902, making the coal barons avert a national catastrophe by meeting some of the labor unions’ demands and putting an end to the strike before winter set in.  His efforts won praise among everyone but industrialists, and the voting public returned a solid Republican majority in the 1902 elections.

When Germany used force to collect debts owed it in Venezuela, TR, standing on the principles of the Monroe Doctrine, assembled the fleet in Puerto Rico, demanding Germany submit its claims to arbitration.  Roosevelt made clear to Europe the reach of America’s sphere of influence in the Western Hemisphere.

And TR’s canal dream was taken up by Congress, which began debating the best route through South America — Nicaragua or Panama (part of Columbia).  The debate was intense, but Roosevelt seized on Panama when that land rebelled against Columbia and declared itself independent.  TR quickly recognized the new state of Panama, sending ships to the area as a show of strength.  Columbia protested, as did many in Congress, but TR simply stated, “I took the Canal Zone.  I … left Congress, not to debate the Canal, but to debate me.”  The deal was formalized in a treaty, negotiated in back rooms and forced on a reluctant but cowed Panama.

“We won a great triumph”
While ever confident in nearly everything in his life, Teddy Roosevelt fretted over the 1904 Presidential election.  He had been in the job for more than three years but he was not elected to it — and none who assumed the office upon the death of a president had ever been elected on his own.  Though with little support in the South and having angered big business, no one in the Republican party challenged him for the nomination. Facing Alton Parker from his home state of New York, TR had little to worry about — he won the popular vote by the widest margin in history.  An ecstatic Roosevelt proclaimed, “We won a great triumph.”


The sweeping victory energized TR — “Tomorrow I shall come into my office in my own right.  Then watch out for me!”  In one month, he announced his Roosevelt Corollary, expanding the Monroe Doctrine by declaring America’s intent on becoming the “police power” of the Western Hemisphere. Combined with his Big Stick diplomacy, TR was determined to ensure America moved boldly onto the world stage.

Business trusts also felt Roosevelt’s determination.  In what he called the Square Deal, TR meant to ensure that workers received fair wages.  Government no longer would work in tandem with big business — TR was fixed upon policing corporations, making sure that anti-trust laws were obeyed and unions were treated fairly.

Two notable instances that best illustrate his determination to regulate were passage of the Hepburn bill and the Meat Inspection Act.  The Hepburn bill, regulated the railroad industry’s pricing on transport rates.  TR felt that railroads had too much control over customers’ lives if they could demand any price for their services.  Upton Sinclair’s scathing novel The Jungle caused a national sensation by exposing the abuses and sanitation problems of the meat packing industry.  Roosevelt demanded and got the Meat Inspection Act, giving the federal government oversight of the meat packing industry.

For all his bluster, Roosevelt acted as the mediator between rival nations and negotiated the end of a war.  In 1904, at the invitation of Kaiser Wilhelm II of Germany, TR arranged for a settlement between Germany, France and Great Britain over the division of Morocco, averting a European war.

However, it was Roosevelt’s mediation in the Russo-Japanese War of 1905 that earned him the most respect in foreign affairs.  With control of the Far East at stake, Japan had defeated Russia’s navy, yet Russia refused to surrender. TR admired Japan’s success but worried such an overwhelming victory might encourage them to seize China and the Philippines.  “I am perfectly well aware that if they [the Japanese] win out, it may possibly mean a struggle between them and us in the future.”  Roosevelt stepped in as a mediator and in Portsmouth, New Hampshire convinced the two powers to sign a peace treaty.  For his efforts, Roosevelt was awarded the 1906 Nobel Prize for Peace.

Japan’s growing presence in the Pacific was one reason TR launched the Great White Fleet in 1907.  Initially limited to the Pacific Ocean, Roosevelt asserted “… that the only thing that will prevent war is the … feeling that we shall not be beaten.” He then ordered the fleet to circumnavigate the world, something that no other world power had done.

Few issues escaped Roosevelt’s eyes.  He was determined to make football safer by devising rule changes for a game that saw dozens of fatalities a year.  He tried to reform the nation’s spelling [He believed words like “through” were archaic] to the ridicule of newspapers and others.  Congress passed a law ordering everyone to follow the “generally accepted dictionaries of the English language.”  He intervened in a racial incident in Brownsville, Texas.  He tripled the size of national forests and hosted a conference on conservation.

Lovely Life
Edith Roosevelt liked being First Lady. She had more time to spend with her husband, and his salary of $50,000 removed the usual money worries that had plagued the family. She was nervous, however, over a possible assassination attempt on her husband. Theodore began to carry a pistol, stating “If a man is willing to give his life for mine, there is no way that he can be prevented from making the attempt.  But such a man must be quicker than I am in the use of his gun.”  Maybe another concern should have been over her children, undoubtedly the rowdiest brood to ever occupy the White House.


The Roosevelt’s were a young family and brought to the White House a robust family of six children between the ages of 17 and four.  Sometimes counted as a seventh child was TR himself, who frolicked with the kids.  “I play with the children almost every night and some child is invariably fearfully damaged in the play; but this does not seem to affect the ardor of their enjoyment.”

Alice, TR’s oldest child, and her father were frequently at odds.  “Father doesn’t care for me, that is to say one eighth as much as he does for the other children,” a sentiment born when Teddy abandoned her for the Dakota Badlands. She was the most outgoing and contrary of all the kids, not unlike her father.  When a friend asked TR if he could do something to control Alice he replied, “I can do one of two things.  I can be President of the United States or I can control Alice.  I cannot possibly do both.”  When a deranged man came to Sagamore Hill carrying a pistol, saying he was going to wed Alice, TR said, “Of course he’s insane.  He wants to marry Alice.”  In 1906, Alice was wed in the White House to Nick Longworth, a ceremony absent of bridesmaids, because Alice did not want to share any attention that day.  It was ironic that Alice later described her father as wanting to be the bride at every wedding and the corpse at every funeral.

Namesake Theodore Jr. was a spitting image of his father in looks and manners.  Much was expected of him but he could hardly live up to the standards of being TR’s oldest son.  He shunned the attention Alice and his father craved and did not do as well at Harvard as the old man.  Knowing how sensitive his son was to criticism, TR wrote, “Good luck, old boy!  You’ll come out all right.  I know you have the stuff in you, and I trust you entirely.”  In later years, TR Jr. embarked on a military career that earned him the rank of general and a Congressional Medal of Honor for heroics at the Normandy invasion in World War II.

Second son Kermit was once described by his father as “a solemn, cunning mite, with queer little friends.”  He followed his father and brother, Ted, to Harvard but he had a love of adventure, traveling to dangerous spots, and became an avid hunter.  He would later travel with TR on African safari and expeditions to South America.  At the outbreak of World War I, he joined the British army, later enlisting in the U.S. Army.

Daughter Ethel was less rambunctious than her siblings but a darling in TR’s eyes.  He once said she was a “small, motherly home-body.”  During World War I she enlisted as a nurse in a Paris hospital where her physician husband also served.  Son Archie was a “sweet-tempered little fellow, not at all combative” like his older brothers.  Archie served as captain in the army in World War I and was severely wounded, later becoming a prosperous Wall Street banker.

Youngest son Quentin was probably the most disrespectful of authority, and his parents knew he was a handful.  To Quentin’s teacher TR wrote, “Mrs. Roosevelt and I have no scruples whatever against corporal punishment…. If you find him defying your authority or committing any serious misdeed, then let me know and I will whip him.”  Despite his rebellious nature, Quentin was loved as the baby of the family.  Tragically, Quentin, a pilot in World War I was shot down and killed, one of the lowest points in the lives of his parents.

Back in the Arena
The end of his presidency was a bittersweet one to TR.  He could look back at all of his accomplishments with pride; with a hand-picked successor there would be a continuation of his agenda.  He was but 50 years of age, however, and still a vigorous man, one who loved the hard work and rigors of the political arena.  Upon winning the 1904 election, he said he would not be a candidate for another term, a decision he soon regretted. “I would cut my hand off right here if I could recall that… statement.”


Updated 11/15/2013