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Douglas Harper's Etymology Dictionary
rough rider

1733, "horse-breaker," from rough (adj. or adv.) + rider. In specific military use, a non-commissioned officer in cavalry regiments, from 1802; meaning "irregular cavalryman" is attested from 1884.

Wikipedia
Rough Rider (film)

Rough Rider is a documentary film which was first shown on RTÉ television on 28 July 2014. The documentary, which was filmed over two years features former Irish professional cyclist Paul Kimmage. It is set against the fall of Lance Armstrong for doping offences in 2012 and follows Kimmage as a journalist during the 2013 Tour de France where he questions what is being done to remove the doping culture in professional cycling since the release of his book Rough Ride in 1990. The film is directed by Adrian McCarthy.

Rough Rider (Rank)

Rough Rider is a now defunct rank in the Royal Regiment of Artillery of the British Army and was a rank equivalent to Private. It was previously used in the British and British Colonial Forces and was the rank was commonly displayed as a spur. Rough rider was also later used as an appointment for what others might call 'Assistant Instructor, equitation'. This latter use could result in designations such as Bombardier 'Rough Rider'.

Usage examples of "rough rider".

Marshal in New Mexico, a deputy sheriff in the Oklahoma Territory, a Rough Rider with Roosevelt at San Juan Hill, a soldier in the Philippine Insurrection and the Boxer Rebellion, a horse breaker for the British and possibly as a mercenary for both sides in the Boer War, as a mercenary for Madero in Mexico, as a Wild West show performer, and as the highest-paid movie actor of his time.