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In the autumn of 1830 he moved to New York State and attended the academy at Canandaigua where he began his study of law. Realizing that his mother wouldn’t be unable to support him through his courses, he was determined to go to the west, and on June 24, 1833, he set out for Cleveland, Ohio, where he was dangerously ill with fever for four months. He then visited Cincinnati, Louisville, St. Louis, and Jacksonville, Illinois, but failed to receive any employment. Feeling Discouraged, he walked to Winchester. Here he found employment as clerk to an auctioneer at an administrator's sale, and was paid six dollars. He studied law at night, and on Saturdays practiced before justices of the peace.
In March 1834, he removed to Jacksonville, obtained his license, and began the regular practice of law. Two weeks after that he addressed a large Democratic meeting in defense of General Jackson's administration. In December 1840, he was appointed secretary of state of Illinois, and in the following February elected a judge of the Supreme Court. In 1843 Judge Douglas was elected to congress by a majority of 400, and he was reelected in 1844 by 1,900, and again in 1846 by over 3,000: but before the term began he was chosen U.S. senator, and took his seat in the senate on March 4, 1847.
The bill for organizing the territories of Kansas and Nebraska, which Douglas reported in January 1854 reopened the whole slavery dispute and caused great popular excitement, as it repealed the part of the Missouri Compromise of 1820 which excluded slavery from the regions of the Louisiana Purchase north of the Mason-Dixon line, and declared the people of any state or territory free to form and regulate their domestic institutions in their own way, subject only to the Constitution of the United States.
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By 1852, Douglas felt politically strong enough to attempt a run for the presidency. He was backed by "Young America," a movement that supported a strong nationalistic policy and called for a return to the principles of Jacksonian democracy. So in 1852, and again in 1856, Douglas was a candidate for the presidential nomination in the national Democratic convention, and though on both occasions he was unsuccessful, he received strong support. The Republicans were united behind Lincoln, while the opposition was divided by regions. Most of the campaign was run by the party organizations, with the candidates taking a very small active part. Stephen Douglas became the first presidential candidate in history to go on a nationwide speaking tour. He traveled to the South where he did not expect to win many electoral votes, but he spoke for the maintenance of the Union. The contest was in effect two contests between Douglas and Lincoln in the North and West and between Breckinridge and Bell in the south. The Republicans ran a very vigorous campaign and then better organization won the day
In an address to the legislature of Illinois, delivered at its request, he urged the oblivion of all party differences, and appealed to his political friends and opponents to unite in support of the government. In a letter dictated for publication during his last illness, he said that but one course was left for patriotic men, and that was to protect the government against all who threatened it. On his deathbed his last coherent words expressed a wish for the preservation of the Union, and his dying message to his sons was to "obey the laws and uphold the constitution."
Douglas died from typhoid fever on June 3, 1861 at Chicago, where he was buried on the shore of Lake Michigan. The site was afterwards bought by the state, and a monument with a statue by Leonard Volk now stands over his grave. In person Douglas was small, standing about 5’ in height, but his large head and massive chest and shoulders gave him the popular nick-name "The Little Giant". His voice was strong and carried far, he had little grace of delivery, and his gestures were often violent. As a resourceful political leader, and an adroit, ready, skilful, he has had few equals in American history.