Roosevelt In Cuba

Theodore Roosevelt was going to Cuba when war with Spain broke out, and no power on earth was going to stop him.  As Assistant Secretary of the Navy, he had fought, schemed, and maneuvered to get an officer’s commission, and he had prevailed. 

His superiors thought he was foolish in the extreme, but they did not understand the workings of  Theodore Roosevelt’s mind.  After much pestering and badgering, Congress eventually authorized the formation of three cavalry regiments from the Western territories.  Dr. Leonard Wood, Roosevelt’s close friend, would command one of these, and Roosevelt himself would serve as his executive officer with the rank of lieutenant colonel.  “This was entirely satisfactory to both the President and the Secretary [of the Navy],” Roosevelt somewhat misleadingly wrote later.

The regiment would come to be called the “Rough Riders,” a moniker that Roosevelt positively relished.  It was an odd, motley group of adventurers:  cowpokes, miners, police officers, Ivy Leaguers, and Native Americans were represented, as well as professions and backgrounds of every sort.  “They were to a man born adventurers, in every sense of the word,” he noted proudly.  But before allowing them to be sworn in, Roosevelt made it clear what he expected of them.  He gathered the final selectees together and told them that they should be prepared not just to fight, but to perform every weary, monotonous task of the soldier’s life.  “I warned them,” he wrote, “that work that was merely irksome and disagreeable must be faced as readily as work that was dangerous, and that no complaint of any kind must be made; and I told them that they were entirely at liberty not to go, but that after they had once signed there could then be no backing out.”

Roosevelt related an amusing anecdote of an enlistee named Pollock, a full-blooded Pawnee Indian.  “I never suspected him of having a sense of humor until one day, at the end of our stay in Cuba, as he was sitting in the Adjutant’s tent working over the returns, there turned up a trooper of the First who had been acting as barber.  Eyeing him with immoveable face Pollock asked, in a guttural voice:  ‘Do you cut hair?’ The man answered, ‘Yes.’  And Pollock continued, ‘Then you’d better cut mine…[I] don’t want to wear my hair long like a wild Indian when I’m in civilized warfare.’”

It is amusing to discover that derisive nicknames were just as common then as with military men now.  Roosevelt writes:

The men speedily gave one another nicknames, largely conferred in a spirit of derision, their basis lying in contrast.  A brave but fastidious member of a well-known Eastern club, who was serving in the ranks, was christened “Tough Ike”…One unlucky and simple-minded cow-puncher, who had never been east of the Great Plains in his life, unwarily boasted that he had an aunt in New York, and ever afterward went by the name of “Metropolitan Bill.”  A huge red-headed Irishman was named “Sheeny Solomon.”  A young Jew who developed into one of the best fighters in the regiment accepted, with entire equanimity, the name “Pork-chop.”  One [professional gambler] who was almost abnormally quiet and gentle, was called “Hell Roarer”; while another, who was in point of language and deportment his exact antithesis, was christened “Prayerful James.”

Scrounging food and supplies for his men became a Rooseveltian speciality.  He would requisition or appropriate beans, cans of tomatoes, and whatever else was needed using every available artifice, even spending his own money when necessary.  But he had no illusions about the pitiless nature of war.  Once contact with the Spaniards commenced, he fought with unrelenting ferocity, and made sure his men did also.  During one period of movement under fire, he was forced to take extreme measures:

No man was allowed to drop out to help the wounded.  It was hard to leave them there in the jungle, where they might not be found again until the vultures and the land-crabs came, but war is a grim game and there was no choice.  One of the men shot was Harry Heffner of G Troop, who was mortally wounded through the hips.  He fell without uttering a sound, and two of his companions dragged him behind a tree.  Here he propped himself up and asked to be given his canteen and his rifle, which I handed to him.  He then again began shooting, and continued loading and firing until the line moved forward and we left him alone, dying in the gloomy shade.  When we found him again after the fight, he was dead.

One time, as Roosevelt was riding down the line, calling his troopers to advance, he came upon a man lying behind a bush.  He ordered the man to rise and advance.  When the man did not move quickly enough, Roosevelt chided him, “Are you afraid to stand up when I am on horseback?”  The man was then hit by gunfire, which traveled through him lengthwise.  Roosevelt noted, “I, who was on horseback in the open, was unhurt, and the man lying flat on the ground in the cover beside me was killed.”  Such are the vagaries of war. 

Roosevelt makes some observations about command that those who have been in leadership positions will recognize as timeless.  First, it is a mistake for an officer to become too familiar with his men, not matter how good they are.  Second, it is a mistake to seek popularity either by showing weakness or mollycoddling one’s men.  “They will never respect a commander who does not enforce discipline, who does not know his duty, and who is not willing both himself to encounter and to make them encounter every species of danger and hardship when necessary.”  Third, an officer should carefully look after his men, should see they are well fed and well sheltered, and should ensure that their camp is kept in a state of military readiness. Any leader who adheres to these three principles can never go wrong. 

Roosevelt was serious about discipline and would not tolerate shirkers of any sort.  He once drew his pistol on a few troopers whom he believed were trying to slink back to the rear during a fight.  Fortunately the incident was a misunderstanding.  When his regiment was disbanded at the end of the war, many Rough Riders had lost their jobs or were too weak to return to work at once.  There were also the dependent families of the deceased men that had to be cared for, in this era before institutional veterans benefits.  Roosevelt personally collected money to distribute to such families.  He wrote to one woman, a teacher in an academy in the Indian Territory who had some pupils who had become Rough Riders.  She responded as follows:

My Dear Colonel Roosevelt:

I did not at once reply to your letter of September 23rd, because I waited for a time to see if there should be need among any our Rough Riders of the money you so kindly offered.  Some of the boys are poor, and in one or two cases they seemed to me really needy, but they all said no.  More than once I saw the tears come to their eyes, at thought of your care for them, as I told them of your letter.  Did you hear any echoes of our Indian war-whoops over your election?  They were pretty loud…I am planning to entertain all the Rough Riders in this vicinity some evening during my holiday vacation…

Pardon me for burdening you with all these details, but I suppose I am like your boys, who say, “The Colonel was always as ready to listen to a private as to as major-general. 

Wishing you and yours the very best gifts the season can bring, I am,

Very Truly Yours,

Alice M. Robertson



Read more about leadership principles in the new translation of Lives of the Great Commanders: