Montauk Life



Col. Teddy Roosevelt


1998 marks the 100th anniversary of the Spanish, American war. This was America's first major step into the international arena, the first in a string of overseas military adventures stretching from San Juan Hill to Desert Storm. Our resounding success in this relatively minor conflict confirmed America's position as a military and colonial power to be reckoned with by its European forefathers. Although it lasted barely 10 weeks, from June through August of 1898, our baptism in fire produced a number of national heroes. Foremost amongst them were Commodore George Dewey, commander of the Navy's Pacific Fleet, and Lt. Col. Teddy Roosevelt, second in command of the First United States Volunteer Calvary, better known as the Rough Riders.


The origins of the Spanish, American War were a combination of America's genuine concern for Spanish intervention in our hemisphere, and the growing political belief that in order to become a great power, we needed to expand our influence here, and in the Pacific. Both of these led to a confrontation with the still vital empire of Spain. Nearby Cuba had been a colony of Spain since the end of the 17th century, and over the course of her rule, Spain had ruled the island with an iron fist. Indifferent to either Cuban or American sentiment, Spain seized Cuban lands and assets, exported her natural resources, and dominated every aspect of Cuban life. During the 1860's and '90's, popular revolutions rocked Cuba, and Spain put them down with brutal efficiency. The Spanish garrison was commanded by General Valeriano Weyler, commonly known as "Butcher" Weyler, because of his ruthless tactics.

America had always maintained strong business interests in Cuba, and those interests were put at risk by Spain's capricious rule of the island. Inflammatory newspaper reports added fuel to the national fire, with their graphic reports of innocent Cubans slaughtered at the hands of barbaric Spanish overlords. As 1898 wore on, Americans demanded action in Cuba, politically if possible, militarily if necessary. Pure sentiment also mixed with a greater strategic aim. Confrontation with Spain over Cuba would also put into play other Spanish interests vital to American expansion in the Pacific, principal among which was the Philippines. The Philippines and the Pacific in general, were seen as their next natural sphere of influence for the Americans, and if war with Spain brought those strategic islands under our flag, so much the better.


The Spanish, American War was the first time the United States committed troops and ships to a two theater war, the Philippines in the Pacific, and Cuba to our south. The Philippine campaign would be the first battle fought, and waged solely at sea. The plan called for the Navy's Asiatic fleet to steam for Manila harbor at first news of war, engage the Spanish fleet there, and if successful, cut Spain off from the archipelago. This strategy depended on our technically superior forces ability to overwhelm the numerically superior, but antiquated Spanish fleet. Ships and strategy aside, this bold move also depended on a Commander aggressive enough to carry out his duties nearly half way across the globe from Washington's central command. Once committed there was no turning back, once difficulties presented themselves there was no chain of command to rely on. Sink or swim, it was his battle to win or lose. History will always remember him, Commodore George Dewey, 30 year naval veteran, seasoned in the Civil War battles of New Orleans and Ft. Pierce, and as pugnacious a sailor as ever held command in the Navy. He was appointed to this position in the summer of 1898, with the considerable help of the then Assistant Secretary of the Navy, one Teddy Roosevelt.

Newly elected President McKinley has only appointed Roosevelt himself to the Navy's second highest position, in early 1987. Determined to prepare the service for what he envisioned as an inevitable battle with Spain, he threw himself into preparations for the coming struggles. Not only did TR feel war was inevitable, he thought it essential to the evolving political future of the republic. His first speech to the Naval War College that summer summed up his view of the world, "No triumph of peace is quite so great as the supreme triumph of war. It may be that at some time in the dim future of the race, the need for war will vanish. But that time is yet ages distant. As yet no nation can hold it's place in the world, or can do any work worth doing, unless it stands ready to guard it's rights with an armed hand." Teddy was confident he could provide the armed hand, and in Dewey he had an Iron Commodore to guide it.


The American Asiatic Fleet consisted of the heavy cruiser Olympia, the protected cruisers Raleigh, Baltimore and Boston, the gun boats Petrel and Concord, and a revenue cutter, the McCulloch. They were stationed in Hong Kong when news came of the outbreak of hostilities. The American fleet was a modern force, amply armed with rapid, fire main guns, thick armor, capable of good speed, and crewed with well trained, although inexperienced, sailors and officers. Dewey's orders were simple, enter Manila harbor, engage the Spanish fleet, and blow it out of the water. The Spanish fleet, although nearly 40 in number, was primarily comprised of small gun boats and support ships. Its main ships were no match for the Americans, in particular the flagship, the "Castilla", a wooden cruiser from the fading age of sail. Dewey's major obstacle was not so much the opposing fleet, as the fortifications that guarded Manila harbor. Mined at it's entrance, guarded by the island fortress of Corregidor, and within range of the many shore batteries in Manila, Dewey would have to force his way past these defenses before engaging the Spanish. He arrived off the Philippine coast at midnight on May 1, 1898, and under cover of darkness began to pick his way through the harbor defenses. Although sighted and fired upon by the shore batteries, he guided his fleet untouched into the heart of the harbor, and waited for first light. Promptly at 5:45AM, with dawn illuminating the Spanish fleet at anchor in the heart of the harbor, Dewey issued the most famous order of the Spanish, American War. Turning to the Captain of the Olympia, he said "You may fire when ready, Gridley!" With that the 8' main batteries of the fleet came alive and the early morning sky of Manila erupted with a cascade of fire and flying steel. Within minutes Dewey's guns had found the range, and the trapped Spanish ships were engulfed in fire and smoke. Gallantly the Spanish returned fire, but their fate was sealed. Dewey made four passes at the Spanish fleet, and by the end of the fourth every capital ship of the fleet lay burning, sunk or adrift. It was a thoroughly one sided triumph, with not a single American ship materially damaged, and not a single American life lost. The Spanish counted nearly 400 dead and wounded. It was the most glorious victory in the history of the Navy, and marked the end of Spain's influence in the Pacific.


Half way round the earth, in Washington, President McKinley received the news of the great battle with relief and pride. However, the battle of Manila did not end the war. Scarcely 100 miles off the US coast lay Spanish held Cuba, garrisoned by a substantial army, and hostile to American interests there. No naval force could impose its will on Cuba, in order to force the Spanish out a full scale invasion would have to be mounted. This would also be a first for America's military, and a risk of her prestige. McKinley may have had his doubts about the venture, but one man was willing to risk everything, in order to make it succeed.

In 1897, Theodore Roosevelt was already a well known national figure, hero of the frontier, vigorous patriot, champion of American values, and most importantly, chief spokesman for an aggressive, expansionist American foreign policy. At the beginning of 1897, Roosevelt was in a perfect position to prepare the nation for what he believed to be an inevitable conflict with Spain. Appointed Assistant Secretary of the Navy, by President McKinley, Roosevelt oversaw the expansion and modernization of the Navy that resulted in Dewey's overpowering advantage at Manila. It was also Teddy, who would be instrumental in organizing and leading the force that would oust the Spanish from Cuba.

In the summer of '98, with hostilities on the horizon, Teddy agonized over his role in the upcoming war. Always a man of action, he knew his place was on the battlefield, not in the rear. At the age of 40 he took a fateful gamble. Determined to serve, not merely direct, he resigned from the Navy Dept. to organize and lead a crack regiment of volunteers for the Cuban invasion. Formally named the 1st United States Volunteer Calvary, they quickly became known as Teddy's Rough Riders.

As soon as word spread that the colorful Roosevelt was looking for volunteers, the War office was swamped with requests to serve. 23,000 applied to ride with Teddy, roughly 2,000 were accepted. The unit Roosevelt assembled was unlike anything the Army had seen before, or since. They came from far and wide, Princeton football players, full blooded Pawnee Indians, aristocratic English dandies, trail wise cowboys, polo players, and Rhodes Scholars. Drawn from every state and social strata, the prototypical Rough Rider was equal parts cowboy and soldier, men who could out ride and out fight the Spanish every day of the week. Traditional military experience was helpful, but not required.

Roosevelt assembled him men in San Antonio, where, in typical Teddy style, he whipped them into army shape. Day after miserable day, they marched, rode, shot, and paraded under the scorching, Texas sun. Inspired by the infectiously energetic Roosevelt, the Rough Riders gave it their all. It wasn't pretty, but within a few short weeks together this disparate gang became the fierce, fearless unit that Teddy needed to break the grip of the Spanish on Cuba. By mid, June they were ready, and Teddy and his beloved Rough Riders boarded trains for Tampa, Florida and the Cuban invasion.


All his adult life Roosevelt had preached the necessity, and nobility of war. Now he finally had his chance to put his principle to the test. On the 20th of June, 1898, he and his Rough Riders began their short, but glorious, campaign in Cuba. Landing on the southern coast, near the small city of Daiquiri, the Rough Riders were one of the first units to come ashore. That week they and the other American forces marched and fought their way through the interior, toward the principal Cuban garrison, at Santiago. The Spanish resistance was fierce along the way, and a number of Rough Riders killed and wounded. Roosevelt himself came under fire a number of times, and earned the nickname "Old Icebox" for his calm courage.

Clancey Pitts worked as a bellman in those high rolling The morning of July 1, 1898, found the Rough Riders within sight of the hills that defended Santiago. Assigned the task of capturing the heavily armed high ground, Teddy assembled his troops for what he would later call, "the great day of my life". After a brief bombardment, the 1st American Volunteer Cavalry began its assault. The hill was steep, and covered in dense underbrush. Sniper bullets whirled around the men, crashing into Rough Riders to Teddy's right and left. Artillery burst all around. At times the advance hesitated, but Teddy led them on. "Forward March", he yelled above the crash of battle, and the Rough Riders surged forward. With Teddy at the head, the Rough Riders at last gained the top of the hill, San Juan Hill. Not once, but twice, Teddy led his men along the ridge to root out the Spanish units.

TR & Rough Riders on San Juan Hill
TR & Rough Riders
on San Juan Hill

The battle for Santiago was the last major conflict of the Cuba campaign. Together with the many other troops of the American force, Teddy and the Rough Riders forced the surrender of the Santiago garrison, and the collapse of Spanish opposition on the island. Unlike Dewey's battle, this American victory came at a heavy price. The Spanish in Cuba fought well, and American blood flowed freely. The Rough Riders in particular took casualties at an alarming rate. It was reported on Jul 4, 1898, that of the 568 Rough Riders landed in Cuba, only 339 were fit for service. The rest were dead, wounded or sick. Roosevelt, and his fearless fellows, had proven their courage under fire. The American people would never forget them. July 1 was by far the most glorious day in Roosevelt's storied life. By the time the newspapers and wire services were done, he had become the most famous man in America! Teddy and his Rough Riders, pounding up San Juan Hill, were installed in the pantheon of American 19th century mythology. In one short afternoon's battle, the Spanish, American War was for all intents and purpose ended, Teddy's fame cemented, and America's domination of the Western Hemisphere certified. All that was left was to bring the troops home for a ticker tape parade down Broadway! That's where Montauk comes into the picture.


TR in Montauk 1898
TR in Montauk 1898

The one small problem with having conquered Cuba was a rather nasty little disease, called yellow fever. During the course of the action, over 29,000 American troops had been exposed to it, along with nearly every other exotic, infectious disease known to be fatal to 19th century medicine. Winning the war was grand, but what to do with the troops? Demobilizing 29,000 potentially inflected soldiers, and sending them back home could well have been caused epidemics from San Fran to the Big Apple! Keeping them in Cuba could have been nearly as disastrous. As TR pleaded to the War Dept. on July 31, " The army must be moved at once, or perish. As the army can be safely moved now, the person responsible for preventing such a move will be responsible for the unnecessary loss of many thousands of lives." The military had to arrive at a reasonable solution, and they settled on relocating those troops to Montauk, while they recovered.

Montauk was a perfect choice, completely isolated, uninhabited save for a few herdsmen, available by either deep water transport or railroad, and still only a few hours train ride from New York. As strange as it seems today, medical wisdom of the time even recommended Montauk for it's prevailing off, shore winds. It was believed that infectious diseases were airborne, and our predominant Northerly breezes would flush the germs harmlessly out to sea.

With little discussion, and even less advance warning, 29,000 Spanish American veterans set sail from Cuba for Montauk. The first ships arrived at what we still call Rough Riders Landing, on Fort Pond Bay, on the morning of August 14, 1898. Waiting for them was a small, but exuberant crowd, including a brass band playing the "Battle Cry of the Republic." The crowd roared as the hero of San Juan Hill, Roosevelt himself, was the first down the gang plank of his flag ship, the "Miami". Asked by a reporter how he felt, TR replied in typical style "I'm in a disgracefully healthy condition! I've had a bully time and a bully fight! I feel as strong as a Bull Moose!" That first day was glorious, what followed was a near disaster. Although the military had conquered Cuba, it floundered in Montauk. The troops who arrived here at Camp Wykoff, as it was called, were in dire need of rest, food, clothing, sanitary facilities, and medical care. Unfortunately, there was little of any in Montauk when they arrived. Once off the transports it was a quick march inland, to a sprawling tent city thrown up from the shores of Fort Pond Bay south to Ditch Plains, and east to Third House. There the veterans of America's first great international war sat, while the military bureaucracy of its day struggled to provision Montauk.

"Starving Men at Montauk" cried the New York Journal, "Story of Horrors Hourly Grow Worse", "It is Murder That is Being Done at Montauk", the headlines were overblown, but the problems were real. Erecting a complete military base, in the middle of Montauk's barren landscape was problem enough, complicated even more by the unique, medical situation. Hundreds of tents had to be pitched, miles of telephone wire run, wells sunk, latrines dug, field hospitals and kitchens erected, not to mention the food and provisions needed daily. Montauk was overwhelmed with transport ships waiting to off load, railroad cars clogging the single train track into town, and the hue and cry of 29,000 sick soldiers.

As it became apparent the military lacked the ability to run Camp Wykoff, help arrived from unexpected sources. First the good towns people of the East End pitched in with much needed food and hospitality. Concerned private citizens from East Hampton in particular, did their part to ease the soldier's plight. Trains stopping at the East Hampton station were met with fresh food and gifts, soldiers healthy enough to leave the Camp were welcomed into private homes, many families visited the Camp with baskets of food. It was more than just a gesture of good will, as one distraught East Hamptonite put it, "It is no exaggeration to say that some of the food brought down by me yesterday saved lives, and I beg everyone in the name of humanity not to relax their efforts". Help also came from another, unexpected source, the Women's National War Relief Association. Founded by, and comprised of some of the most prominent women of their day, this group of dedicated volunteers threw themselves into the care and rehabilitation of the army troops. Lead by Mrs. Emily Warren Roebling, wife of Brooklyn Bridge builder John Roebling, this was no ladies lunch outing. The privileged women who came to Montauk as nurses, rolled up their sleeves, and worked as hard as anyone to get the boys back on their feet. They took charge of providing clean sheets and bedding for the men, bottled water and milk, much appreciated delicacies such as fresh fruits, and jams. They even paid for clean clothes and new boots for the poorly outfitted troops.

The Women's Assoc. did as much as any one to transform Camp Wykoff from a logistical nightmare to a working operation. One, a Miss Reubena Hyde Walworth, a Vassar graduate and teacher who had come to Montauk as a nurse, paid the ultimate price, when she died of typhoid fever contracted tending the men. She was afforded a full military funeral, and was laid to rest wrapped in her country's flag. She joined the 126 men who died of fever at Camp Wykoff that summer. Considering the Army's general incompetence, it's surprising the toll was so low.

President McKinley arrives in Montauk
President McKinley
arrives in Montauk

By the beginning of September the health of the troops had improved to the point where true demobilization could begin. But before Camp Wykoff would fade away, Montauk would witness one last historic moment. On September 1, a flag bedecked train pulled into the Montauk station. With the flourish and fan fare befitting him, the substantial figure of President McKinley emerged from the train to inspect and congratulate his troops. As he gazed upon the assembled masses, his eye caught the unmistakable sight of a certain ex, Ass. Secretary of the Navy in the ranks, McKinley stepped down from his carriage, Teddy dismounted and the two met in the center of the troops. As they shook hands, and exchanged warm greetings, the men of the 1st American Volunteer Calvary exploded with hurrahs and cheers. At that moment, the most powerful man in the country stood side by side with the most famous.

Teddy Roosevelt accepting the Remington statue
Teddy Roosevelt accepting
the Remington statue

Teddy stayed in Montauk with his Rough Riders until their marching orders were finally cut on September 13. That day a mustering out ceremony was organized, for Teddy to bid farewell to his beloved men. But before the great orator had his moment, his men had theirs. They wished to present the Col. with "a very slight token of their admiration, love and esteem". A Private Murphy then uncovered what had been hidden by a field blanket on a table in the center of the formation. It had hidden a bronze bronco, buster statue, by the famous Western artist, Frederick Remington. Overcome with emotion, and speechless for one of the few times in his life, Teddy choked back real tears.

"This is something I shall hand down to my children, and I shall value more than the weapons I carried through the campaign". Roosevelt then asked the Rough Riders to come forward so that he could shake their hands. As they filed past, Roosevelt thanked each of them for their comradeship, bravery, and devotion. In those last moments together, Teddy and his Rough Riders wrote the last page in their glorious history. By dark the 1st American Volunteer Calvary was but a memory, as they shuttled through the dark, bound for New York City and home. The glory of San Juan Hill would out last them all, while the dismal experience at Camp Wykoff would fade as quickly as the summer's night.



An exhibition celebrating the Rough Riders stay in Montauk is currently on exhibit at the aptly named Teddy Roosevelt County Park, three miles east of the village. Site of last years Roosevelt Centennial celebration, it features rare photos, military memerobilia, and Roosevelt personal affects. The gift shop also has an excellent history of the Rough Riders for sale, as well as other books on the period. A bully time, is guaranteed for all!


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