Jesse Applegate (July 5, 1811 – April 22, 1888) was an American pioneer who led a large group of settlers to Oregon Country along the Oregon Trail.

Jesse Applegate (July 5, 1811 – April 22, 1888) was an American pioneer who led a large group of settlers to Oregon Country along the Oregon Trail. He was a powerful member of Oregon's early government and was instrumental in establishing the Applegate Trail as an alternative route to the Oregon Trail.

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Jesse Applegate was born on July 5, 1811, in Henry County, Kentucky. He moved to Missouri with his family in 1821 and quickly found work in the law office of Edward Bates. He went to seminary in Illinois and worked as a schoolteacher, clerk, and deputy surveyor to the Missouri Surveyor General, where he met men like Jedediah Smith, William Sublette, and David Edward Jackson, who were instrumental in laying out the Oregon Trail. On March 13, 1831, Applegate married Cynthia Ann Parker and moved to the Osage River near Osceola, Missouri, the following year. His farmstead lasted twelve years, with the labour force primarily consisting of slaves from neighbouring farms, despite Applegate's lack of personal ownership.

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Along with his brothers Charles and Lindsay and their families, he joined what became known as the "Great Migration of 1843" on the Oregon Trail. He became one of the leaders of the expedition after it split into two parties over a dispute about whether the large amounts of livestock being driven by some members of the group would slow down their travel. Applegate's party became known as the "cow column" and the other party was called the "light column". He memorialized the journey in an essay that gained fame in the ensuing decades, "A Day with the Cow Column in 1843".

After leaving their guide Marcus Whitman at his mission and abandoning their wagons at Fort Walla Walla, the Applegate brothers built boats for travelling down the Columbia River to Fort Vancouver. Near The Dalles, a boat capsized and Jesse and Lindsay each lost a son to drowning. Lindsay later wrote, "We resolved if we remained in the country, to find a better way for others who might wish to emigrate."

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Jesse Applegate established a farm in present-day Polk County in 1844, as well as a mill and worked as a surveyor, including surveying the site of Oregon City. During the elections for the Legislative Committee of the Provisional Government of Oregon in 1845, Applegate was elected without his knowledge as the representative of Yamhill County (one of five counties in Oregon at the time). Soon after, he was appointed, along with David Hill and Robert Newell, to draft a revision of the Organic Laws, which was eventually voted on and adopted by the settler population.

The Provisional Government had tense relations with the Hudson's Bay Company, based across the Columbia River at Fort Vancouver, and Applegate paved the way for a political settlement. He drafted a new oath for government officials that included both British subjects and American citizens. The Yamhill legislator persuaded John McLoughlin and James Douglas to join the Provisional Government during a meeting. A previous incident involving Americans squatting on Fort Vancouver's farmland, as well as his subsequent threat to burn down the Fort, contributed to the agreement. The Hudson's Bay Company was to be taxed only on transactions with settlers, according to the Provisional Government. Douglas was elected to the newly established Vancouver district, which included the lands north of the Columbia. Applegate was able to get duelling banned after learning of an upcoming fight between two men over a woman.

The Cayuse War was one of the last events in Oregon in which Applegate was involved. Following the Whitman massacre, a commission led by Applegate approached Douglas, requesting a loan from the HBC to fund a military intervention. Douglas stated that he was not authorised to make a loan, but he did recommend Peter Ogden's peacekeeping mission to the Cayuse. Applegates, Asa Lovejoy, and George Abernethy contributed to a loan of $999.41, and others contributed as well. Because of the settler's isolation, Willamette Valley communities Joseph Meek and Applegate were tasked with requesting assistance from other parts of the United States. Meek travelled to Washington, D.C., to deliver an appeal for military support written by Applegate. Applegate had to turn back while attempting to reach his destination of California due to the mountain passes being impassable in the winter.

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For settlers wishing to reach the Willamette Valley, a safer alternative to boating the Columbia River was still required. The Barlow Road was considered the worst stretch of the Oregon Trail, despite being safer than the river crossing. The Meek Cutoff, another attempt to find an alternate route, resulted in the deaths of at least 23 people. Applegate drafted legislation that gave him the authority to survey a southern route to the Willamette Valley that avoided the Columbia River. Daniel Waldo, an emigrant from the Great Migration of 1843, was appointed as the expedition's outfitter. The Applegate Trail, also known as the South Road, began at Fort Hall in present-day Idaho and followed the Humboldt River before crossing the Klamath Basin. Jesse Thornton travelled the trail in its first year, 1846, and later accused Applegate of starving his party to give him a stronger negotiating position for relief. Men surveying the road, on the other hand, defended Applegate.

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In 1849, Applegate established a land claim in the Umpqua Valley. Yoncalla was named after the local Indian tribe. He represented Umpqua County at the Oregon Constitutional Convention in 1857, but he left before the convention was finished. In an 1865 speech, Applegate stated that "every member of the Commonwealth, regardless of which sex, what colour, or where born, if free from the tutelage imposed by domestic relations, should have the right to vote, if morally and mentally qualified to do so." Applegate died on April 22, 1888, and is buried with his wife in a small private cemetery near Yoncalla, Oregon.

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