Prior to his service in the Spanish–American War, Roosevelt had already seen reserve military service from 1882 to 1886 with the New York National Guard. Commissioned on August 1, 1882 as a 2nd Lieutenant with B Company, 8th Regiment, he was promoted to Captain and company commander a year later, and he remained in command until he resigned his commission.[71][72][73][74][75]When the United States and Spain declared war against each other in late April 1898, Roosevelt resigned from his civilian leadership job with the Navy on May 6 and formed the First US Volunteer Cavalry Regiment along with Army Colonel Leonard Wood.[76] Referred to by the press as the "Rough Riders", the regiment was one of many temporary units active only for the duration of the war.[77]After securing modern multiple-round Krag smokeless carbines, Lieutenant Colonel Roosevelt arrived on May 15.[73] The regiment trained for several weeks in San Antonio, Texas, and in his autobiography Roosevelt wrote that his prior National Guard experience had been invaluable, in that it enabled him to immediately begin teaching his men basic soldiering skills.[78] The Rough Riders used some standard issue gear and some of their own design, purchased with gift money. Diversity characterized the regiment, which included Ivy Leaguers, professional and amateur athletes, upscale gentlemen as well as cowboys, frontiersmen, Native Americans, hunters, miners, prospectors, former soldiers, tradesmen, and sheriffs. The Rough Riders were part of the cavalry division commanded by former Confederate general Joseph Wheeler. It was one of three divisions in the V Corps under Lieutenant General William Rufus Shafter. Roosevelt and his men departed Tampa on June 13, landed in Daiquiri, Cuba, on June 23, 1898, and marched to Siboney. Wheeler sent parts of the 1st and 10th Regular Cavalry on the lower road northwest and sent the "Rough Riders" on the parallel road running along a ridge up from the beach. To throw off his infantry rival, Wheeler left one regiment of his Cavalry Division, the 9th, at Siboney so that he could claim that his move north was only a limited reconnaissance if things went wrong. Roosevelt was promoted to colonel and took command of the regiment when Wood was put in command of the brigade.Main article: Battle of Las GuasimasThe Rough Riders had a short, minor skirmish known as the Battle of Las Guasimas; they fought their way through Spanish resistance and, together with the Regulars, forced the Spaniards to abandon their positions.[79]Main article: Battle of San Juan HillColonel Roosevelt and the Rough Riders after capturing Kettle Hill along with members of the 3rd Volunteers and the regular Army black 10th CavalryUnder his leadership, the Rough Riders became famous for the charge up Kettle Hill on July 1, 1898, while supporting the regulars. Roosevelt had the only horse, and rode back and forth between rifle pits at the forefront of the advance up Kettle Hill, an advance that he urged despite the absence of any orders from superiors. He was forced to walk up the last part of Kettle Hill, because his horse had been entangled in barbed wire. The victories came at a cost of 200 killed and 1000 wounded.[80]Roosevelt commented on his role in the battles: "On the day of the big fight I had to ask my men to do a deed that European military writers consider utterly impossible of performance, that is, to attack over open ground an unshaken infantry armed with the best modern repeating rifles behind a formidable system of entrenchments. The only way to get them to do it in the way it had to be done was to lead them myself."[81]Roosevelt as a veteranIn August, Roosevelt and other officers demanded that the soldiers be returned home. Roosevelt always recalled the Battle of Kettle Hill (part of the San Juan Heights) as "the great day of my life" and "my crowded hour". In 2001, Roosevelt was posthumously awarded the Medal of Honor for his actions; he had been nominated during the war, but Army officials, annoyed at his grabbing the headlines, blocked it.[82] After returning to civilian life, Roosevelt preferred to be known as "Colonel Roosevelt" or "The Colonel". However, "Teddy" remained much more popular with the public, even though Roosevelt openly despised it. Men working closely with Roosevelt customarily called him "Colonel" or "Theodore".[83]
Governor of New York
Chicago newspaper sees cowboy-TR campaigning for governor
After leaving the Army, Roosevelt discovered that New York Republicans needed him, because their current governor was tainted by scandal and would probably lose. He campaigned vigorously on his war record, winning the 1898 state election by a historical margin of 1%.[84]
As governor, Roosevelt learned much about ongoing economic issues and political techniques that later proved valuable in his presidency. He was exposed to the problems of trusts, monopolies, labor relations, and conservation. Chessman argues that Ro
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