Goofs

There are several mirror shots as the Spanish are preparing to defend against the American attack on San Juan and Kettle Hills. In particular, several Spanish soldiers are shown shooting Mausers that are suddenly left-handed, and two other Spaniards feed a Maxim machine gun from the left when the German later tells Roosevelt that the Maxim feeds from the right.

Mirror-image shot while Roosevelt is preparing to sound the charge up San Juan Hill.

In the final scene in 1920 Nash states that Roosevelt was in poor health. Roosevelt died in 1919.

William Tiffany was not killed in action. He survived the Battle of San Juan Heights unhurt and was given a battlefield commission as a second lieutenant, but was among several Rough Riders who contracted and died of yellow fever while awaiting their return home after Spanish surrender.

At several points in the film, General Wheeler refers to Nathan Bedford Forrest, another Confederate cavalry general, as his "old friend" and quotes him approvingly. However, Wheeler and Forrest had a notoriously rocky relationship, stemming from the Kentucky Campaign when General Braxton Bragg transfered most of Forrest's troops to Wheeler's command. After a failed attack on Dover, Tennessee in February 1863, an enraged Forrest told Wheeler that "I will be in my coffin before I fight again under your command," leading ultimately to Forrest's transfer elsewhere. Wheeler may have grudgingly respected Forrest, but it's unlikely that he would have upheld him as the ideal cavalry officer given their antagonistic wartime relationship.

Captain Bucky O'Neil is buried in Arlington National Cemetary, not in the Arizona Wilderness.

John Hay was not in fact Secretary of State during the time of the Spanish-American War. William R. Day was in that position, Hay was the Ambassador to Great Britain and was appointed Secretary of State after the war had concluded.

There were no German Advisors present at the battle of San Juan Hill. Also the German Maxim guns shown were not used by the Spaniards in Cuba.

In the final scene subtitled "22 Years Later" (placing the scene in 1920), Nash refers to "the First World War," a term not used until the start of the Second, in 1939.

When the captured machine gun is used by the rough riders to target San Juan Hill, Roosevelt orders them to "elevate 20 meters". Any US army commands given in 1898 would have been in feet, moreover the cowboys would have not known what 20 meters was.

Roosevelt refers to a captured German military advisor as a "Hun." The derogatory epithet "Hun" for German soldiers was first used (by the German Kaiser Wilhelm II himself,) during the Chinese Boxer Rebellion of 1901 and did not become widely used until World War One, both well after the Spanish-American War.

The Film ends with Henry Nash, now a millionaire, visiting the graves of his comrades circa 1920. In fact, the real Henry Nash died in the Philippines in 1902 as a teacher.

During their training at Fort Sam Houston in San Antonio, Texas, the USV is shown riding through dense pine forests. There are no such pine forests on or near Fort Sam Houston.

After Roosevelt's first encounter with the Spanish, he is walking away from the battle scene getting an update on who was wounded and killed. During this scene, on the bottom left corner you can see a boom mic enter and leave the picture.