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Exile to Submission, Death to Dishonor: General Joseph Orville Shelby Stuart W. Sanders few Civil war Cavalry CommaNders rivaled Joseph orville shelby. aN expert at hit-and-run tactics and adept at covering a retreating army, Shelby displayed charm, tenacity, and fighting ability. Most often compared to his childhood friend John Hunt Morgan because both made slashing raids into Union-occupied, border-state territory, historians have called Shelby a “Kentucky aristocrat” and a “sort of Trans-Mississippi Forrest.” In addition, writers have noted that his troops participated “in every major campaign in Missouri and Arkansas,” where they became “the very flower of the [transMississippi ] army” and “perhaps the best cavalry unit in the West.” Although Federal troops frequently equated Shelby’s troopers with bloodthirsty guerrillas who roamed western Missouri, Union Major General Alfred Pleasanton, who fought Confederate cavalry from Virginia to Missouri (including that of J. E. B. Stuart), said that “Shelby was the best cavalry general of the South. Under other conditions, he would have been one of the best in the world.” His men echoed this sentiment, reputedly stating, “You’ve heard of . . . Jeb Stuart’s Ride around McClellan? Hell, brother, Jo Shelby rode around missouri !” There was a price for this hard riding. Shelby’s adjutant, John N. Edwards, remarked, “Every step that Shelby took ran over in blood.”1 Shelby was born in Lexington, Kentucky, on December 12, 1830, into a prominent Bluegrass family. His grandfather was a cousin to Kentucky’s first governor, Isaac Shelby. When Joseph’s father died in 1835, he left Jo with a sizable trust. Eight years later, on July 6, 1843, Joseph’s widowed mother, Anna Boswell Shelby, married Benjamin Gratz, a wealthy lawyer and hemp rope manufacturer whose friends included Henry Clay. The marriage gave Jo Shelby a set of cousins and friends who rose to prominence. Montgomery Blair, Francis P. Blair Jr., and Benjamin Gratz Brown were cousins by marriage . Montgomery became President Abraham Lincoln’s postmaster general, Stuart W. Sanders 234 Francis helped keep Missouri in the Union, and Benjamin became a renowned Missouri politician, U.S. senator, and governor of the Show Me State.2 In addition, Jo moved into the Gratz home in downtown Lexington, two doors away from John Hunt Morgan. The two became friends, and their wartime careers in many instances mirrored each other.3 Gratz provided Shelby with his early education. In 1845, at age fifteen, he entered Lexington’s Transylvania University, located up the street from the Gratz mansion. After three years there, he finished school in his stepfather’s hometown of Philadelphia. When Shelby returned to Lexington, he joined the family hemp business.4 In 1851, Shelby turned twenty-one and received his eighty-thousanddollar inheritance. The next year he followed two cousins, Frank Blair and Gratz Brown, to Missouri, where he eventually settled in Waverly in Lafayette County. There, Shelby and his stepbrother, Howard Gratz, established a hemp-rope walk, run with slave labor. Having grown up around slavery— Shelby’s stepfather, for example, had sixty-five slaves in 1850 and twelve slaves when he retired in 1860—Shelby used the institution for his benefit. He also farmed and owned a steamboat, and by 1860, he was one of the wealthiest slave owners in Missouri.5 When the Kansas Territory erupted into chaos after the KansasNebraska Act, Shelby led a group of forty well-armed, proslavery fighters into Kansas to vote in local elections. As border tensions exploded into fighting, Shelby gained combat and leadership experience. He later recalled, “I was in Kansas at the head of an armed force about that time. I was there to kill FreeState men. I did kill them. I am now ashamed of myself for having done so, but then times were different from what they are now, and that is what I went there for . . . the trouble we started on the border bore fruit for ten years.”6 Shelby found more than violence during this period. In 1858, he married a distant cousin, Elizabeth N. Shelby. Throughout their marriage, they were blessed with seven children, but within three years, after Shelby cast his lot with the Confederacy, the family was frequently separated.7 As a man of considerable influence, both sides courted Shelby when the Civil War erupted. In early 1861, he met his cousin, Francis Blair, in St. Louis. Blair, working for Missouri Unionism, offered Shelby a Federal commission, but he declined. He was already actively supporting the Confederacy, having purchased...

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