Some people believe that the Rough Riders were almost all cowboys from out West. After all, it had earned the nickname “The Cowboy Regiment.”
But that wasn’t entirely the case, as you shall see. Brahmins from New England with refined backgrounds also joined the Rough Riders.
Men from every New England state volunteered for Teddy Roosevelt’s U.S. 1st Volunteer Cavalry, better known as the Rough Riders. Massachusetts had as many as 25. As a matter of fact, the actual commander of the unit, Leonard Wood, hailed from New Hampshire. Frederic Remington featured Woodbury Kane from Rhode Island in his famous painting of the immortal charge up San Juan Hill.
Roosevelt had four recruiting stations out West, in Arizona, New Mexico, Texas and the Oklahoma/Indian Territories. He had vast experience in the West and knew the cowboys already knew how to ride and shoot. But Roosevelt knew another target-rich area full of ready-for-action men: His wealthy, pedigreed friends throughout New York and New England.
Roosevelt put out the word. They responded in droves from polo clubs, boxing clubs, duck blinds, steeplechase courses, yacht clubs, Ivy League athletic fields and glee clubs. Many had graduated from Harvard.
One Rough Rider, James McClintock, who hailed from California, said they were in it for the adventure.
The Rough Riders are the stuff of legend, having generated a movie, a television show and, of course, a President. They were, however, one of the shortest lived units in American military history. They only existed for four months and 13 days before they disbanded.
Rhode Island Rough Riders
Woodbury Kane, Newport;Joseph S. Stevens, Newport; Norman Maxwell, Newport; Charles Hatch, Newport; Joseph F. Flynn, Cranston.
Woodbury Kane, a classmate of Teddy Roosevelt’s at Harvard, was born in Newport, a cousin of John Jacob Astor IV. A noted yachtsman, he belonged to the New York Yacht Club and served on the crew of the Columbia in the 1899 America’s Cup Race. He was also a noted big game hunter.
After graduation, he lived the life of a bon vivant in Newport and New York. In April 1898 he and other East Coast friends joined the U.S. 1st Volunteer Cavalry.
After enlistment, he, William Tiffany and other East Coast friends donated two $7,500 Colt machine guns to the unit. When the unit expanded to a thousand men he received a lieutenant’s commission.
While serving in the Rough Riders he was always noted for being dressed to a T, no matter the conditions. While leading K Troop in the charge on San Juan Hill, he was wounded in the forearm. Kane was awarded a citation for gallantry and promoted to captain.
He spent the rest of his life living the life of a dandy until a heart attack cut him down at the age of 46. His obituary noted he left no children, but he did leave his beloved polo pony.
Ira A. Hill, Grand Isle; Wallace Batchelder, Chester.
Wallace Batchelder graduated from Chester Academy in Chester, Vt., before enlisting in the Rough Riders. He later fought in the Philippines under General Wood. After his service he returned to Vermont, where he became a lawyer and chaired the state’s committee to elect Roosevelt President of the United States in 1904. He later broke with Roosevelt, who in 1912 sent him a telegram telling him not to support any candidate who didn’t support Roosevelt. Batchelder replied he wouldn’t support Roosevelt.
New Hampshire Rough Riders
Dudley S. Dean, Laconia; Walter F. Hickey, Nashua; Leonard Wood, Winchester.
Leonard Wood was the actual commander of the Rough Riders; Teddy Roosevelt was his second in command.
A descendant of four Mayflower passengers, he trained as a physician at Harvard Medical School. He served as a major general in the Army. When he came to command the U.S. 1st Volunteer Cavalry in Cuba, he was a seasoned Indian fighter in the West and had already been awarded the Medal of Honor. After the Spanish-American War, he served as Governor-General of the Philippines and contended for the Republican nomination for President in 1920.
Dean was an All American football quarterback for Harvard from 1888 to 1890. He participated in the charge on San Juan Hill. That was not to be his last military adventure. During World War II, he served as a lieutenant colonel In the U.S. Army Air Force. He was the executive producer of the play Winged Victory, which ran from November 1943 to May 1944. He lived until the age of 79, passing away in 1950.
Dudley’s son John H. Dean played football for Harvard too. At Harvard, he befriended Joseph P. Kennedy and they spent summers together at Cohassett, Mass.
Guy Muncie, Calais; Harrison J. Holt, Portland; Frederick C. Wesley, Bangor.
Harrison Holt graduated from Phillips Andover and Harvard. Upon his Harvard graduation in 1898 he enlisted with Roosevelt’s Rough Riders. After the war and some business ventures in Mexico he joined the New York Globe and Commercial Advertiser as a reporter. Later in life he wrote novels and detective stories, including The Calendared Isles, a Romance of Casco Bay (read it here) and Midnight at Mears House.
Edward C. Hall, Wallingford.
Unlike most of the Ivy League Rough Riders, Edward Hall graduated from Yale, not Harvard. Upon graduation in 1894, he went to work for Westinghouse and did a brief stint at a North Dakota ranch before enlisting with the Rough Riders. After the war he joined General Electric in Lynn, Mass., then transferred to the Schenectady office, where he died in 1912.
Harry A. Curtis, Boston; Prescott H. Belknap, Brookline; John D. Hubbell, Boston; Rufus K. Thomas, Boston; Wellman H. Saunders, Salem; John P. Gardner, Boston; Guy H. Scull, Boston; Harry A. Davis, Boston; Francis B. Crowninshield, Marblehead; William H. Mitchell, Salem; Winslow Clark, Milton; Edward F. Donnelly, Boston; Michael F. Hogan; William T. James, Fitchburg; Arthur M. Leroy, Boston; Raymond Morse, Springfield; Edward A. O’Brien, Charlestown; William J. Tudor, Boston; Harry C. White, Somerville.
Francis Boardman Crowninshield, another Harvard graduate, went on to become a noted international yachtsman. He fought with Troop K of the Rough Riders and took part in the charge up San Juan Hill. In 1900, he married Louise DuPont from the famous chemical family. In 1911, he won the King of Spain’s Cup in Spain, now among his many trophies at the Eastern Yacht Club in Marblehead, Mass.
About the author of this story: Leo Caisse of East Providence, R.I., passed away in 2020. He published the book, The Civilian Conservation Corps: A Guide to Their Works in Rhode Island. He also published a number of historical articles, including Ears On the World in America in World War II Magazine, October, 2017. Leo earned a B.A. and M.A. in American History from Providence College and he lived in East Providence, R.I.
This story updated in 2022.