
1) Cavalryman with TR 2) Equestrian 3) Follower of Roosevelt 4) Harsh jockey 5) Hero of 1898 6) Horseback rider 7) Horseman 8) Spanish-american war figure 9) Teddy Roosevelt 10) Teddy Roosevelt was one 11) Teddy Roosevelt, notably
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https://www.crosswordclues.com/clue/roughrider

• (n.) An officer or enlisted man in the 1st U. S. Volunteer Cavalry, a regiment raised for the Spanish war of 1898, composed mostly of Western cowboys and hunters and Eastern college athletes and sportsmen, largely organized, and later commanded, by Theodore Roosevelt. Sometimes, locally, a member of any of various volunteer cavalry commands ...
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http://thinkexist.com/dictionary/meaning/roughrider/
Rough'rid`er noun One who breaks horses; especially
(Mil.) , a noncommissioned officer in the British cavalry, whose duty is to assist the riding master.
Found on
http://www.encyclo.co.uk/webster/R/97

Formerly, a roughrider was a non-commissioned officer in the British cavalry, whose duty was to assist the riding master.
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http://www.probertencyclopaedia.com/browse/FR.HTM

[
n] - a horseman skilled at breaking wild horses to the saddle
Found on
http://www.webdictionary.co.uk/definition.php?query=roughrider
noun a horseman skilled at breaking wild horses to the saddle
Found on
https://www.encyclo.co.uk/local/20974
No exact match found.