As the war moved farther south, Kilpatrick returned to Virginia and spent the rest of the summer and that fall slugging away at J.E.B. Stuart's horsemen. He took a short respite from this grueling work when he used his artillery to bombard two Confederate-manned gunboats in the Rappahannock. Afterward the slugging matches resumed, and he fought fa series of battles at and near Brandy Station. In one of these he achieved a modest feat by escaping from an encirclement set by Stuart's men. However, this was later described in slightly grander terms by one regimental historian: "Kilpatrick thus escaped serious injury, defeated his pursuers, and presented to the beholders one of the grandest sights witnessed in the New World."

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During the winter of 1863­64 Kilpatrick sat in winter quarters and did some thinking. He reassessed his career, and re-evaluated his goals. At length he decided that his future was to be in terms of elective office: first, he would become governor of his native state, and then the President of the United States. And he determined to prosecute the war in a way that would assure the attainment of these goals. He knew that his cateer, and therefore his future, had been jeopardized at Gettysburg and in subsequent campaigning. Clearly he needed a plan that would give him new prominence and would once again splash his name across the North's newspapers.

After much deliberation he conceived such a plan. He would enter Richmond with his cavalry, free the Union prisoners there, and perhaps even capture Confederate officials. The more he thought about it, the more eager he grew to test teh scheme. he boasted to others of its brilliance, and it was not long before his boasts were circulating through the army, and northward. President Lincoln eventually heard of it, and began to wonder. In this third year of hostilities the President was almost desperately searching for a blueprint for peace. Despite Kilpatrick's uneven past performances, Lincoln called the cavalryman to the White House and asked for details. Kilpatrick was more than happy to oblige. When he learned that Lincoln was anxious to distribute through Virginia copies of his amnesty proclamation for secessionists who wished to come back into the Union, he assured the President that his expedition would be the ideal means to that end. Lincoln finally gave his approval for the raid, and a joyous Kilpatrick returned south to put it to the test.

On the morning of February 28, 1864 he started his cavalry toward Richmond from Stevensburg, Virginia. His 4,000 troopers rode in two columns. Under his personal command 3,500 of them were to strike the city from the north; 500 in a detachment led by a boyish, onelegged colonel named Ulric Dahlgren, were to attack the Capital from the south. Dahlgren had been taken into Kilpatrick's plans because he was eager to "smell hell"–and, incidentally, because he had impeccable social credentials (his father was a prominent Federal admiral).

The raid began smoothly enough. The columns proceeded south by widely divergent routes, planning to make a concerted attack on Richmond–believed to be only thinly guarded this winter–on March 1. Both Kilpatrick and Dahlgren met with little opposition in their destruction of railroad lines and private property, and distributed hundreds of copies of the President's proclamation.

But the Yankees' coming had been anticipated by the Confederates. Just outside Richmond Kilpatrick was hit by units of Rebel infantry, artillery, and cavalry. He faltered and then retreated–beaten back fro n the city when success was nearly in his hands. Dahlgren, meanwhile, was stymied by an unfordable river and reached the city too late to coordinate an attack with Kilpatrick. The colonel and his men were sent on a disorderly retreat through a winter storm and were finally surrounded by Rebel home guardsmen. In an ambush fight the detachment was cut to pieces and Dahlgren met a tragic death at 21.

His hopes crippled, Kilpatrick retreated to Fort Monroe. There he fretted that instead of enhancing his reputation, the raid had broken it beyond repair. His anxiety deepened when a national controversy developed around papers found on Dahlgren's body, stating that the raiders had planned to burn Richmond and kill President Jefferson Davis and his Cabinet.

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