A post on Facebook about Theodore Roosevelt revealed a piece of history that was quite shocking mostly because I’ve never seen anything about this while there are multiple articles, TV spots and museum entries in south Florida.

Roosevelt and his Rough Riders spent some time in the Ybor City neighborhood of Tampa before disembarking for the Spanish-American War in Cuba in 1898 where the famous San Juan Hill battle took place.

The Rough Riders were in Tampa just a short time, but while there made some history that is today enshrined in a Tampa museum along with several monuments in Ybor City.

Most of us who are aware of Ybor City know that it was home to hundreds of cigar manufacturers in the 1890s. Many of the workers in those factories were Cubans and Roosevelt and his Rough Riders camped there which led to some clashes with the Cuban immigrants.

History tells us that Tampa Bay was the perfect spot to launch a troop ship because the imminent battle would take place due south of the Florida city of 15,000 at the time.

There are numerous mentions of North Dakota in the historical accounts in Florida. After assembling a regiment of fighters from all over the nation, the unit was transported to San Antonio for training before boarding trains for Tampa that included food and horses.

Apparently, the nickname Rough Riders came about because of Roosevelt’s time owning a ranch in Dakota Territory and that he helped recruit the Soldiers.

Roosevelt, at the time was a lieutenant colonel and was second in command to Col. Leonard Wood, of which Fort Leonardwood in Missouri is named. Roosevelt had resigned his post as assistant secretary of the Navy to lead the Rough Riders since he was a strong proponent of the Cuban war of independence.

Although we’ve seen and heard a lot about the Rough Riders in Cuba, they had another nickname, Wood’s Weary Walkers that reflected their dissatisfaction that despite being cavalry, they ended up fighting in Cuba as infantry since most of their horses didn’t accompany them from Florida.

The men were in Tampa in late May 1898 and arrived in Cuba on June 23, 1898. Not all of the Rough Riders’ 12 companies departed which weakened the regiment, according to Roosevelt. At the same time about a fourth of the trained Soldiers had died of malaria or yellow fever.

These troops wore wool uniforms, so you can imagine how hot it must have been in Florida and Cuba during the summer with that attire. The Soldiers were uncomfortable in their camp while reporters covering the war stayed nearby in the lush Tampa Bay Hotel. The Army headquarters was housed in the same hotel.

Also at that time in history, because the Civil War had taken such a toll on both sides of the fighting, the United States became mostly isolationist and because of it, the Army had a dangerously low manpower of 28,000. The Rough Riders totaled 1,000 during their stay in Ybor City.

While the Rough Riders waited for orders to leave for Cuba, much of the food went bad in the Florida heat and humidity. As a result of that, Roosevelt used his influence as assistant secretary of the Navy to get his men on a ship that was meant for another regiment.

In 2019, Clay Risen, an editor at the New York Times, spent some time in Tampa and Ybor City to get information for a book he wrote called The Crowded Hour, a title that Roosevelt himself had put on the San Juan Hill battle.

Risen found plenty of information in Tampa that included journals and letters of the men who made up the Rough Riders. The book was released in late 2019 and was one of 100 notable books described in the New York Times that year.
Because of Roosevelt’s influence in the Tampa Bay region, the 1st U.S. Volunteer Cavalry Regiment – Rough Riders Inc., known locally as the Teddy Roosevelt Museum, was formed in 1978 to create and perpetuate the unique accomplishments of Roosevelt and the Rough Riders.

The museum is located near Tampa’s Channel District at 601 19th Street which houses a museum, meeting facilities, a float barn and administrative offices. Anyone interested in visiting may call 813-248-1898 or email a request to (office@tamparoughriders.org)