Theodore Roosevelt As Rough Rider  by Rosemary McKittrick

Photo courtesy of Swann Auction Galleries.

The U.S.S. Maine moved into Havana harbor on Jan. 25, 1898 and dropped anchor.  The American warship’s presence was a warning to potential pro-Spanish Cuban rioters to stay away from Americans living in Cuba and their property.  The rioters were demonstrating against the idea of Cuba’s independence from Spain.  The United States was in favor.     

Life was a great adventure to Roosevelt and he wanted to see battle.  It was a way to demonstrate his toughness.

The battleship with its four long guns seemed to be a good deterrent.  But on February 15 a huge explosion lit up the night sky and roared through the city.  The Maine’s front end had been blown off. 

The ship was on fire and sinking.  It went down in 40 feet of water.  Parts were still burning when the sun came up.  Of the 355 men on board, 253 were dead.  Seven more died later.

Was it an accident?  An act of terrorism?  To this day no one knows for sure.

Hostility broke out between America and Spain over the disaster.  It was just the type of fight Asst. Sec. of the Navy Theodore Roosevelt was looking for.  

Life was a great adventure to Roosevelt and he wanted to see battle.  It was a way to demonstrate his toughness.

Roosevelt told friends if a war broke out he would resign as Asst. Sec. of the Navy and join the Army.  He loved ships but had no training as a naval officer.  He understood being an Army officer. 

The Spanish-American War was a given and Roosevelt accepted a commission as a lieutenant colonel in a volunteer United States Army.  He wanted the best men America had to offer to fight next to him.  He chose a collection of rough-and-tumble characters for his regiment. 

Roosevelt picked cowboys, African Americans, Irishman, Jews, Native Americans, athletes, police officers and college students.  The regiment called themselves the Rough Riders.

“Rough, rough we’re the stuff.

We want to fight, and can’t get enough,


That was their motto.

Roosevelt included his personal publicists in the regiment and put them in charge of documenting the regiment’s heroic exploits.      

The Rough Riders’ uniform was a dark blue flannel shirt, breeches, tan canvas leggings and a wide-brimmed tan hat.  The men were equipped with six shooter Colt revolvers kept in black leather holsters on their right hip.

Thanks to the publicists and the press, Roosevelt’s military exploits in the Spanish-American War echoed throughout America.  Reporters covering the war wrote countless stories about Roosevelt and his Rough Riders.   

It took the Americans 111 days to overcome the Spanish kingdom.  Spain lost all of its colonies and much of its Army and Navy surrendered. 

Hailed as a hero, the publicity paved the way for Roosevelt’s political climb, ultimately ending in his presidency.

On April 22, Swann Auction Galleries featured a selection of Roosevelt’s items in its Autographs auction.  Among the collection was a photograph of Roosevelt in his Rough Rider uniform. 

Signed and inscribed as President, the 22 inch by 18 inch, 1904 portrait taken by the Pach Brothers shows President Roosevelt standing beside a tent in Camp Wikoff, Montauk. 

The photo sold in the auction for $15,600. 

Pres. Theodore Roosevelt

Military Commission; partly-printed; appointing William B. Homer Lt. Col. In Artillery Corps; signed and countersigned by Acting Sec. of War Robert Shaw Oliver; July 3, 1906; 19 inches by 15 ½ inches approximate;  $1,140. 

Photograph; signed; family portrait by W.S. Ritch; Roosevelt surrounded by family; May, 1918; 4 ¾ inches by 6 inches;  $1,200.

Photograph; bust portrait; signed and inscribed; by Harris Ewing; 1910; 13 inches by 9 inches approximate;  $1,968.

Typed Signed Letter; defense against charge of maligning Thomas Paine; with a 12-line autograph postscript; March 1918;  $4,800.             

Rosemary McKittrick is a storyteller.  For 26 years she has brought the world of collecting to life in her column.  Her website is a mother lode of information about art, antiques and collectibles.  Rosemary received her education in the trenches working as a professional appraiser.

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