The
Rough Riders

Theodore Roosevelt 

Within days after the call for volunteers for the First U.S. Cavalry was issued, Colonel Wood and Lieutenant Colonel Roosevelt were deluged with eager young men from all over the United States.  "The difficulty in organizing was not in selecting, but in rejecting men."  Various states offered entire, organized local militias, but Wood could only build his regiment from those within the three allotted states and the Indian Territory. Bucky O'Neill, the Mayor of Prescott, AZ and a famous frontier sheriff volunteered and was commissioned Captain of Troop A.  Captain Llewellen of New Mexico was one of the most noted peace-officers of the frontier, already shot four times in battles with outlaws.  Lieutenant Ballard was another former peace officer who had gained Western fame for breaking up the infamous Black Jack Gang.  Benjamin Franklin Daniels, one ear partially gone (it had been bitten off in a fight) had been the Marshall of Dodge City in its heyday, before joining the Rough Riders along with the deputy marshal of Cripple Creek, Colorado, Sherman Bell.

Yet another of the Rough Riders was a fellow named SMITH who, months later upon discharge requested a letter of recommendation from Roosevelt.  "You see, Colonel, my real name isn't Smith, it's Yancy," he said.  "I had to change it, because three or four years ago I had a little trouble with a gentleman, and--er--well, in fact, I had to kill him; and the District Attorney, he had it in for me, and so I just skipped the country; and now, if it ever should be brought up against me, I should like to show your certificate as to my character!"

Colonel Wood preceded Roosevelt to San Antonio to begin assembling the men of the regiment while the latter finished up his duties in the Capitol before resigning as Under Secretary of the Navy.  When Wood arrived, most of his soldiers from Arizona, New Mexico and Oklahoma were there and waiting to begin training.  Within days, additional men arrived from the Indian Territories.  The new recruits included Cherokee Bill, Happy Jack of Arizona, Smoky Moore, The Dude, Hell Roarer, Tough Ike, and Rattlesnake Pete.  Among the ranks were at least four former or current ministers and several former members of the famed Texas Rangers.

Originally the First United States Volunteers was allotted 780 men, but as the would-be soldiers gathered, the authorized strength was raised to 1,000.  This allowed room for a few volunteers from the East, eager young men from prestigious universities like Harvard, Yale, and Princeton.  Many of these were star athletes from their schools, and they mixed with the collage of rough-edged frontiersmen in a chaotic and often volatile environment. 

Former Princeton football standout James Robb Church came to the Rough Riders after a variety of careers as an explorer, hunter, cook in a lumber camp, and even service as a doctor on an emigrant ship.  Church was appointed as the regiment's assistant surgeon.  

Colonel Wood began immediately trying to turn his strange assortment volunteers into a tangible unit, despite frequent misgivings.  At one point the commander commented, "If we don't get them to Cuba quickly to fight the Spaniards there is a great danger they'll be fighting one another."

 

Back in the Nation's capitol, Lieutenant Colonel Roosevelt resigned his Navy Department post and spent a week concluding his affairs both with the department, and on behalf of his Rough Riders.  Literally hundreds of volunteer units were being marshaled across the United States, and with less than two dozen Army quartermasters to supply them all, the war-time Army was suffering from a series of bad administrative decisions.  Among the worst, most soldiers (as well as the Marines being sent to Guantanamo Bay) were outfitted in hot, wool uniforms... a serious error for men expected to fight in a tropical climate.

From his position in Washington, D.C. Lieutenant Colonel Theodore Roosevelt "pulled the necessary strings" to outfit the Rough Riders in khaki.  On Saturday April 30th, Roosevelt sent a message to Brooks Brothers of New York requesting a tailored "lieutenant-colonel's uniform without yellow on the collar, and with leggings...so I shall have it here by next Saturday (May 7)."  It was one of many Rough Rider expenses for which he would pay out of his own pocket, and Brooks Brothers met the requested deadline.

Even far more important than the uniforms however, was the need for solid weaponry.  Many of the volunteers from the west came to the regiment with their own Winchesters which would fire the Government cartridge.  Those who preferred these personal weapons were allowed to retain them.  Officers were armed with pistols, but the men of the regiment were, at Colonel Wood's insistence and thanks in large part to Roosevelt's connections, outfitted with the new Krag-Jorgensen rifles which had the advantage of using smokeless powder.

Finally wrapping up his duties in Washington, Roosevelt departed for San Antonio.  On May 15th he arrived, looking impressive in his tailored Brooks Brothers uniform, to join Colonel Wood and meet his Rough Riders.

For two weeks Roosevelt worked to continue the training of his Rough Riders while Colonel Wood finished the process of procuring the necessary saddles, arms, ammunition, and other material.  As the month of May came to a close, soldiers from training posts around the country began to converge on Tampa, Florida.  It was from here that Major General William Shafter would transport his Fifth Army Corps to the shores of Cuba.  On May 25th the President called for 75,000 additional volunteers to supplement his war-time army, and the first soldiers of the Philippine Expeditionary Force departed San Francisco for Manila.  At San Antonio the Rough Riders continued their drilling and exercises, chaffing to be called to service and worried that the war might end before they got their opportunity.  Then their orders came through.  On May 29th, even as Admiral Sampson's ships blockaded the harbor at Santiago, the Rough Riders headed for the rail yard to begin the 4-day trip to Tampa.

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The regiment was broken up into seven sections for the journey east, Colonel Wood departing first with three sections, while Roosevelt's remaining four sections worked well past midnight to load their horses and their gear.  In addition to 1,000 men and their mounts, the regiment had 150 pack mules so it was a sizable process simplified only by the fact that the men carried virtually no personal luggage, only the supplies necessary for warfare.

Along the route the trains were required to make periodic stops so that the horses could be tended.  During these stops the enlisted men were allowed brief liberties under the supervision of the non-commissioned officers.  "Everywhere the people came out to greet us and cheer us.  They brought us flowers; they brought us watermelons and other fruits, and sometimes jugs and pails of milk--all of which we greatly appreciated," Roosevelt later recalled.  Despite the warm reception and the frequent stops, it was a long and tiring journey that took its toll on the men and their leaders.  By the time the train reached the end of the infamous one-track railway that ended in Tampa, the Rough Riders were ready to fight someone... anyone.

"We disembarked in a perfect welter of confusion," Roosevelt recalled.  "Everything connected with both military and railroad matters was in an almost inextricable tangle."

Some 30,000 American soldiers had been arriving in Tampa in previous days, and the transport and organization of such a sizable force and its equipment had taxed the abilities of both the military leadership and the railroads.  No one met Colonel Wood and his Rough Riders when they arrived.  There was no indication as to where the unit was to make camp.  No one appeared to issue food for the first day of the regiment's tenure in Tampa.  Wood, Roosevelt and the other officers purchased food for their men out of their own pockets.  When at last they learned where the regiment was to make camp, they had to seize wagons to carry their supplies from the train to their camp.  

Wood and Roosevelt did their best to bring order out of the chaos and organize their men and prepare them for war.  During the days that followed, the men continued their training in the nearby woods, and conducted at least one mounted drill of the entire regiment.  And then their orders arrived...the Rough Riders were going to war.

The notice that Shafter's Fifth Corps, including the Rough Riders, would depart at once for an unknown destination was bitter-sweet news.  Sadly, the Cavalry soldiers resigned themselves to the news that their horses would have to be left behind.  They would be going to war as a dismounted cavalry unit.

More devastating however, was the news that of the Rough Riders 12 troops, only eight would be joining the expedition.  Each troop consisted of 70 men, which meant that of the regiment's 840 members, 560 would finally get their opportunity for action.  It also meant that 280 eager, would-be heroes would have to be left behind.  "I saw more than one, both among the officers and privates, burst into tears when he found he could not go," Roosevelt wrote.  To the great bulk of them I think it will be a life-long sorrow."

On the evening of June 7th Colonel Wood and Lieutenant Colonel Roosevelt received their orders.  At midnight their eight troops were to meet a train for the 9-mile trip from their camp to Port Tampa where at daybreak they would board their transport ships.  The orders were explicit...if they were not aboard their transport at daybreak, the Rough Riders would be left behind.  Wood and Roosevelt had no intention of allowing that to happen.  Neither realized the challenge meeting that goal would become.

 

By midnight the Rough Riders, or at least the 8 troops selected for combat duty, were waiting at their appointed boarding site.  The First U.S. Cavalry was ready for war...but their trains were not.  The trains were, in fact, no where to be found.  In frustration, Colonel Wood, Lieutenant Colonel Roosevelt, and other of their officers wandered about in search of information.  They found none.

At 3:00 A.M. the Rough Riders received orders to march to an entirely different track, which they promptly did.  Upon arrival at their assigned destination, they again found confusion but no trains.  It was a morning of anxious frustration filled with the worrisome knowledge that, unless the Rough Riders were aboard their sea-going transport at daybreak, they would miss the war.

At 6:00 A.M. a coal train moved down the track, coming from Port Tampa and going in the opposite direction.  Roosevelt and Wood halted the train, seized it, and convinced the engineer to transport the Rough Riders to Port Tampa.  For nine miles the coal train BACKED down the track, but the improvisational commanders reached port with moments to spare...only to find even more, and perhaps even worse, confusion.

As quickly as the appropriated coal train backed its way into Port Tampa, Wood and Roosevelt jumped to the ground and went in search of information as to which transport their men were to board.  Occasionally they managed to find a general officer, but even the highest ranking of the tens of thousands of soldiers scheduled to debark from Port Tampa that morning were lost and confused.  The two commanders separated and spent an hour in search of a quartermaster, meeting again when they located him at nearly the same time.  Colonel Humphrey pointed out in the channel towards the Yucatan and a sickening realization dawned on both Wood and Roosevelt.  In the mass confusion that reigned, the Yucatan had also been assigned as transport for the Second Regular Infantry and for the 71st New York Volunteer Infantry.  The ship would be hard pressed to contain the men of their own regiment, much less all three units.

Colonel Wood seized a stray launch at the docks and directed it to the channel where he boarded the Yucatan.  Meanwhile Lieutenant Colonel Roosevelt literally ran at his top speed, dodging through the milling thousands of soldiers and their tons of supplies, to reach his regiment.  Leaving a guard for their baggage, he double-timed his soldiers back to the dock, arriving even as the Yucatan entered the quay, and promptly boarded her.  Something of a scene developed later when the Second Infantry and the 71st New York realized that the Rough Riders had beaten them to the transport, but Roosevelt faced them down in a situation he described as their: "having arrived a little too late, being a shade less ready than we were in the matter of individual initiative."

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Throughout the day, amid the continued confusion, 16,000 American soldiers and their equipment were loaded aboard the transport ships that would ferry them to the shores of Cuba.  The Rough Riders had been, thanks to the ingenuity and initiative of their commanders, among the first to board.  Their role in the coming conflict seemed assured.  As night fell the Yucatan moved out into the channel and dropped anchor.  When all was ready, the 37 transport and support vessels would depart.

Roosevelt was already more than disgusted with the total confusion he had witnessed throughout the day.  This, and continuing problems ranging from organization to supply and rations for the men of the U.S. Army, would cause him to brazenly criticize the ineptness of the bureaucracy and planning behind the war in the Caribbean.  His outspoken assessment, despite his popularity with the American populace, would come back to haunt him and deprive him of his most coveted recognition, the Medal of Honor.

Among the worst of the blunders was the provision for Shafter's Fifth Corps.  Most of the men, aside from the Rough Riders, were sent into combat in a tropical climate still wearing their wool uniforms.  Rations were even worse.  The men were issued meals that included "canned fresh beef", a foul tasting meat dish devoid of salt.  Throughout the war it became universally hailed as "Embalmed Beef", a major sore spot among all the troops, most of whom refused to eat it.  While combat casualties in the Spanish-American War would be light, the problems with organization, proper uniforms and rations, fresh water, even proper medical supplies, would boost casualties far beyond the limited few deaths to bullets and saber.

As the sun set on June 8th however, the soldiers of the Fifth Corps contented themselves with the fact that at last they were shipping out to Cuba in the first expedition to leave Florida.  Again, fate would deal these eager volunteers another devastating blow.

As the sun rose over the Caribbean on the morning of June 9th to reveal the convoy, each ship tightly packed with hundreds...even thousands...of soldiers and their equipment, the expedition was postponed.  Out in the deeper waters of the Caribbean a Naval officer had witnessed the presence of a large number of ships in the distance, and mistook them for Spanish vessels.  His report raised an immediate concern, and the transport ships in Tampa were ordered to remain anchored while American warships went in search of the Spanish.  For four days they searched the tropical waters, finding no sign of the enemy.  During the period, soldiers aboard the anchored transports did their best to survive the hot sun and cramped quarters while the ships bobbed at anchor.  

As the blunder of the Naval officer became apparent, the battleship Indiana arrived at Port Tampa with 7 auxiliary cruisers, to serve as protective escorts for the troop convoy.  At last, on the evening of June 13th, the Yucatan hoisted anchor and joined the fleet in moving out for Cuba.

A Splendid Little War